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According to Gartner, sales organizations undergo an average of four transformations every two years. Of those, only 11% manage to drive commercial success. For the go-to-market organization, and especially for the enablement function within it, that statistic says a lot. Every single one of those transformations lands on their desk, and the ask is pretty much always the same: move quickly, keep the field informed, and make sure what they’re armed with is 100% accurate. So how do you build an enablement function that can keep up, especially as AI increases the pace of these transformations? Riley Rogers: And welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully. Here to discuss this topic is Rebecca Sharbono, Senior Manager of Sales Enablement at Tanium. Thanks so much for joining us, Rebecca. I’m super excited to hear your take on this one. I know it’s very top of mind for you and the team. Before we jump right into the deep end, could you tell us a little bit about yourself, your background, and your role? Rebecca Sharbono: Riley, thank you so much for having me. As you mentioned, I’m an enablement leader at Tanium, a cybersecurity company. I spend a lot of my time training and enabling people across the go-to-market org and supporting business initiatives that scale across all those go-to-market teams. I have spent years developing people across nonprofits and startups and large corporations. That moment when you see the light bulb go on for someone who’s learning something new or learning a different way to do something, watching them go from unsure to confident, and realizing that I got to play a small part of that, is huge, and that feeling never gets old. Across all of my career, my rule is really simple: leave people better than you found them. And these days, what that means is figuring out how to help teams move at speed without losing trust and craft that makes people really good at their jobs. RR: Let’s dig into it. As so many organizations, yours, mine, are grappling with AI innovation that is truly ceaseless, every day there’s something new, how are you seeing that affect Tanium’s go-to-market priorities? RS: Wow, the struggle is real. What it comes down to is looking at it a couple different ways. Part of me looks at it through a product shift, and then part of me looks at it through a people shift. There’s a shift that’s happening with AI models and with products, and I know specifically with Highspot and with Tanium, there’s a lot of AI that’s in our products. And at the same time, it’s happening in how we build our people. So we’re moving from this idea of we need to train experts to use a complex tool or process, such as Tanium or Highspot, to enable anyone to run at an expert level. When I tie it back to product, our AI platform lets one operator do what used to take a team. My job is making sure that our people, our field, can do the same thing, where they can walk in and perform like a team of experts faster than ever before. When I think about how AI plays into that, it isn’t just in how we sell anymore, it’s the mirror that we’re holding up in how we’re developing talent. RR: I like that. It kind of drives home the point that, yes, it’s changing the way that we can do things, but it’s not changing necessarily what we’re doing. We’re still going to market with relatively similar products. We’re developing our people in similar ways. We just have some different mechanisms, and not only do we have different mechanisms, there’s different kind of priorities and pushes, by which I mean, as you’ve mentioned, we’re moving with greater precision, greater urgency. Where is that pressure kind of coming from for you? RS: This is coming from all over, much like the AI that’s being thrown out there. But I think at its core, there are three places where I can distill it down. Again, I go back to the product. AI-driven tools move faster than training cycles used to. And then I think about the market as a whole. Customers now expect proof of value in weeks, not quarters, not months. They want to see that impact right away. And then the people. Today’s talent doesn’t want a six-month onboarding. They don’t want a two-month onboarding. They want to be useful in week one. And I think what’s interesting is that enablement really sits at the center of all three of these things. RR: I would like to think about this through the lens of a recent example, and maybe slightly less recent now, because again, to the point of new things every day. But given the industry that you’re in, monumental change in the models that are available can send shockwaves through your workforce and your customers, a good example being the release of Claude’s Mythos model. So can you walk us through what it looks like on the enablement side when something so significant drops in your industry? RS: Tanium is a cybersecurity company. We sit within the IT industry, and what we do is help businesses connect their endpoints and have full visibility in real time. Taking a step back a moment, the release of industry disruptors like Mythos, whatever the next thing is, really shows us that the tool capability jumps are now arriving so much faster than most organizations can absorb them, and this is a pressure point. Every time a Mythos level model drops, the ceiling on what’s possible jumps overnight. With that, people’s readiness to speak to it doesn’t jump with it. So what the field needs isn’t necessarily training on the new model, it’s judgment training. They need to know what it means, what it’s capable of, and what it’s not, because the gap changes every few months. So specifically with Mythos, what we identified the field as needing in that moment were a few different things, but they needed them really fast. That goes back to that speed we talked about earlier. They needed to know the capability as a foundation, “Hey, what is this? What does it mean,” so that we can position ourselves as a trusted advisor when we’re talking with prospects and customers. They needed to know the impact, because if they’re talking to a CISO and a SOC analyst, they’re gonna have very different questions, different fears, different requirements for that conversation, and we needed to make sure our field was armed with those right conversations based on the persona they were gonna be speaking with. When we got word that this was released, we stood up an enablement package within, I think it was, a 48-hour timeframe. It was all hands on deck. We had analyst themes to start building the foundation off of, and their insights to work from. Teams across the company, product, enablement, sales, pre-sales, you name it, jumped in to provide the right talk tracks and help us build FAQs. And then we launched everything with a field activation brief just a few days later. RR: As we talked about, you need to move fast, but up until recently, you didn’t necessarily have all of the tools in the toolkit to move quite as quickly as you needed. So what resources and support were the field working with, and what did you see kind of not working? RS: We didn’t have a way to ensure that the field had the most up-to-date information. While we were housing stuff on SharePoint, sometimes if a seller would go in and try to search for a piece of information, it may have pulled something up that was from two years ago, and things change at lightning speed, as we know and as we’ve been talking about. So that was a huge gap. We had ways to create content and measure some activity, but the speed and the impact together, we didn’t have that in real time. And as you can imagine, there were decisions that were being made on instinct or lagging data because the feedback loop just didn’t exist yet. RR: As you were tackling that beast and started building a new way forward focused on speed, what were your early priorities, and how did you get started breaking that down into manageable bits and pieces? RS: It truly is, hey, what’s the endpoint that we’re trying to get to, and then what does that mean for us and how do we prioritize how to get there? When speed becomes a priority, many times I see people creating more stuff. You don’t start with more content. What you need to do is start with clarity. So looking at where the pain was loudest at that time was really important. We’re hearing from sellers that they don’t have what they need. They can’t find the information at the speed they need it. Those were pretty loud pain points right out the get-go. So the first priority is figuring out how we actually move the needle and identify what’s mission critical versus nice to have. Secondly, building the fastest possible feedback loop so that we know within days, not quarters or weeks, if something is working or not. That was really important too, to figure out we need to identify a test group, a beta group, once we’ve looked at some different solutions to get feedback. And thirdly, we have to make it usable by one person without hand-holding, because if it needs an expert to drive it, to understand it, to use it, it’s not actually fast. Those were some of the things that were rattling through my brain as we figured out how to build that foundation, prioritize what we needed, and how we got started. RR: You did the work to figure out what the path forward was. You spoke with people to understand what they needed. You essentially built the vision. Once you started to understand what the North Star was, what were those first few components that you needed to tackle once you had landed on a solution? What is the go-forward plan there? RS: It was basi

According to LinkedIn’s Workplace Learning Report, 49% of L&D professionals say their executives are concerned that employees don’t have the right skills to execute their business strategy. And in busy, fast-paced industries, that gap is becoming a real problem. Because if the product, market, and go-to-market motion are all evolving at once, organizations are left asking the same question: what does it actually look like to build an enablement and a go-to-market model that can keep up and build those skills as they’re needed? Riley Rogers: Hi, and welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully. Here to discuss this topic is Julia Townsend, Go-to-Market Enablement and Business Development Leader at DataRobot. Julia, thank you so much for joining us today. I really appreciate the time. Super excited to hear about the work you’re doing in this arena today. Before we jump in, though, I’d love if you could tell us about yourself, your background, and your role. Julia Townsend: Yeah, great. Thanks for inviting me, and Riley, really appreciate it, and excited to share more about what I do at DataRobot. So yes, I lead the go-to-market enablement and business development function at DataRobot, and if you’ve not heard of us, we are the only end-to-end agent workforce platform for secure, scalable, and production-grade agents. We are based out of Boston, although I am based in the UK, so we do have a global workforce. So when it comes to enablement, I own it globally. Plus, as I said, I also have the business development piece. Pretty interesting role that is fairly unusual within the enablement space. But day-to-day, what that means is a few things. So I run our enablement team, so within that, I have a BDR and sales revenue enablement specialist, I have a go-to-market readiness specialist, and I also have a technical enablement data scientist, which is brilliant. And then I also have our BDR team who are based in Boston. So a little bit about me. So prior to making a career change to working in enablement in the AI ML space, I actually did start out as a BDR myself, then I was an enterprise seller in the SAS observability market for many years. I’ve been with DataRobot for five years. I’ve been through quite a few different distinct eras of where we’ve been. And so started out very early with very hiring-heavy model. We did a lot of in-person boot camps, then we had a bit of a restructure within our business, which is very typical within the AI space. It’s very much up and down, so we had to rebuild the enablement in a much more of a leaner type of practice. And now within the AI agentic era, where the products in the market are moving so, so, so quickly, any of the other early enablement models that we’ve had, it’s really, there’s been a lot of changes. RR: And that leads us very well to kind of the first topic we were gonna touch on, which is the fact that change is abundant and everywhere, especially when you’re working in the AI space. So as you’ve been navigating the enablement journey for the last five years at DataRobot, what has shifted about how you think about enabling sellers from when you first started to what it looks like now? JT: So I guess the biggest shift when I think back to those years is moving away from a very calendar-driven compliance type model towards something that’s much more embedded where the seller is and is very continuous. In previous older years, we were very much all about completion tracking, which in hindsight looks a lot like compliance monitoring. So there were lots of weekly reports on showing who had or hadn’t finished a learning module. We were very big on the stick piece back in the day. And then I guess after we had our organizational restructure a couple of years back, our hiring volume dropped and the business model changed, and the need for big recurring cohort in-person boot camps really evaporated. So that meant that it forced enablement to start pivoting towards much more of a leaner targeted delivery. Tracking forward to today, enablement definitely lives now inside the same sorts of tools and the cadence that sellers already have. We use Highspot, we have the content management and the learning management modules. So that means we’re able to offer very much bite-sized content. So it means that rather than the field having a separate training destination that they have to go into, what we’re providing is very much just part of the weekly workflow for them to be successful. So they’re not visiting stuff occasionally, they’re always in it. So it’s less about building a big curriculum and running it once a year, and it’s much more about treating enablement like a live product. RR: We kind of talked about what it means for enablement as a function to be working amidst this change, but like you alluded to, DataRobot is a company in a market that never really stops moving. So what does that kind of environment demand from you? JT: It is really about speed because we operate in a very competitive environment. There’s a ton of companies out there that are specialist agent builders, they’re there to sell you some sort of agent to help you in a day-to-day life. But then there’s also companies at our level who are also providing platforms, and it’s very, the language is very similar, so it’s very hard to stand out. So when you have an edge with your product development, those USPs, you really have to get the sales team on board with it and talking that language, that new messaging, that new positioning to customers as soon as it’s been created. So speed is very important. What that means for enablement and content is that it has to ship in days or weeks, not quarters. For example, two Sales Plays that we launched last quarter, our Dell seller-to-seller play and our customer expansion play, they both went from kickoff, initial conception, to the field launch on very, very tight dated project plans with weekly status checks, which meant we could launch them in a matter of weeks, whereas in the past, it would take us a lot longer to do that. RR: I’d love to drill down into an example that you mentioned as you were speaking to the speed piece, in a recent instance where that became a necessity. So the Dell partnership. You shipped a Sales Play for it, you enabled the team quickly on the messaging. What did that look like to build, and can you tell us a little bit more about the scenario around it? JT: So DataRobot, we have a fairly new strategic partnership with Dell and Nvidia. As this was a new business drive for us, we had to create a very specific Sales Play that was focused on our reps engaging with Dell reps. And I think this is a little bit different maybe to other enablement functions or what we also did in the past, where plays tend to more focus on the sales process, so things like objection handling play, first meeting play. Whereas this play had a pipeline generation target attached to it, and so the play centered on building early-stage pipeline with Dell sellers, and it was very, very specifically around that. The Dell engagement with our Sales Play ended up being quite a few different types of enablement requirements that are stacked on top of each other for different audiences, but all around roughly the same timeline. So for example, we first launched the Dell seller-to-seller play. This was equipping our own sellers to target and partner with the Dell sales team. We launched this towards the end of Q1. But then coupled with that, we then did some event-specific BDR training. Our BDRs were going to some of these Dell networking events with the sellers and meeting them, and they needed to have the right narrative. They needed to understand some of the vertical specific use cases that would get a Dell seller interest. So we did lots of live role play practice with them to make sure they were able to do that effectively. But yeah, I guess to summarize that piece, it wasn’t just one enablement deliverable, it was four or five different audiences that were wrapped into one Sales Play, but it was very much focused on a pipeline generation target. RR: What was the timing like from we have this partnership to now I need to enable the field to I have enabled the field? How does that differ from maybe a year ago what that would’ve looked like? JT: Yes. So I guess a year ago, it felt like there was more luxury in terms of time, because the Sales Plays then weren’t so much aligned to a specific pipeline target. So if your Sales Play is more around objection handling or first meeting deck, that’s important, but it doesn’t quite have the same impact on what the business needs in terms of a north star metric that will translate into real business revenue and deals closed. So that was one thing that was different. In terms of the timeline, probably took us about four weeks. We really put the heads down with the team. We had a daily project call to work on the content, test it, and ship it out. We ran it like we would a product launch, so using the same sorts of methodologies around that with reviewing, iterating, building, testing, those sorts of things. So that was also different. We had a very tight project management approach to it, which enablement led. Because this was tied to a real revenue metric, it really had the ear of the CRO. It was his prerogative to drive this. So that also was super helpful, was having executive sponsorship all over it, encouraging the reps to lean in, and being the voice of enablement, helping us amplify what we did to help them, and that’s all because the Sales Play was attached to a real revenue goal. RR: Four weeks, that’s a pretty crazy turnaround, I

According to Gartner, 73% of B2B buyers actively avoid suppliers who send irrelevant outreach. That tells us two things. One, personalization is prolific. Many teams are trialing different plays and finding varying degrees of success. Two, personalization is a risky play. Get it wrong, and you might actually do more harm than good. So what does it actually look like to show up in a way that earns a buyer’s attention? Riley Rogers: Welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully. Here to discuss this topic are Molly Donlon, sales activation manager, and Tommy Dauphin, senior account executive at Paylocity. Thank you so much for joining us, both of you. I’m super excited to dive into all of the fun and unconventional ways that you guys are capturing attention, driving engagement, and tackling the beast that is today’s modern buyer. Could you help me kick things off? Just tell me a little bit about yourself, and Molly, I’ll kick it over to you. Molly Donlon: Tommy would have insisted that I start anyway because he’s a gentleman from the South. So I started out in sales as a business development representative in my corporate career, and I actually used Highspot as a BDR. I stayed in sales for three and a half, almost four years, and then fell in love with the strategy behind sales, and especially personalization. I almost felt like an investigator, where I could go and do the research and find something that told me that this person actually would benefit from what we are providing, and then explain how I made that connection. So I decided to help my teammates and my colleagues within sales, rather than put that into practice with clients. It’s been an amazing company and a great journey. RR: Amazing. Well, I’m super interested to hear more about the buyer engagement private investigator lifestyle. Before we do, Tommy, I’ll kick it over to you. Tommy Dauphin: Excellent. Thank you so much, Riley. And, Molly, you are absolutely correct. I was not going first on that one. You were definitely gonna get the first intro there. So Tommy Dauphin here from South Louisiana. Been at Paylocity, it’ll actually make eight years next month. And then before that, I worked at Cintas for 10 years, primarily on the operations side. Paylocity was my first outside sales job. So not only did I have to learn the world of sales, but also the world of HR tech, and all of the things in between. So it’s been quite the journey, but like Molly said, fantastic place to be, and very excited to be here today. RR: Well, I’m looking forward to learning more about everything happening at Paylocity right now. And Molly, I’d love to start with you. You mentioned that one of the things that you loved was doing your own research, and it sounds like it’s not just sellers that are doing their research, it’s also buyers. So when buyers are learning, researching, Googling before they ever talk to a seller, how do you actually get their attention? MD: In a Forbes article, it said that about six in 10 B2B buyers prefer to go through most of the buying process without a sales rep intervening. And HRIS, human resources information system, what we sell, is very complicated, and it has an impact on the whole company. So I find it hard to believe that sales reps will be completely free of participation in the sales process. But I do think we should be leaning into the behaviors and the desires that we’re hearing from buyers. They want to see all of the information available, and that’s why we’ve had such great success with Digital Rooms, for example. The best way to accommodate this behavior is here are the trustworthy resources, so that we can meet you when you’re ready to talk to someone. RR: Okay, so you mentioned needing to create a place where when buyers are researching, they land in a location where they get everything they need, the right messaging that you want them to have, and that then leads them to an actual person that can then usher them through that back half of the sales cycle, or whatever point they reach you. Tommy, I know that you have more than a handful of creative tactics for those get your foot in the door moments. So how do you make a meaningful impression before the conversation starts? TD: I think the number one piece is providing value in every step of the way. In every interaction, there’s gotta be something that I’m bringing to the table, and me showing up and dropping off a business card or a pamphlet or a brochure or something is not cutting it. You have to do more than that. And it’s also a situation where not every person knows how to go through a buying process, because sometimes I’m talking to people who have evaluated their process every 18 months, every two years. But every once in a while, you run into that person who’s said, “We’ve been with our current provider for the last decade.” Well, a lot has changed in the last decade in the world of HRIS, so not only do you have to learn how to buy this product, but you have to then compare, contrast, and figure out the differences, and it can get confusing. The waters get muddy. Everyone starts to look and sound the same, and we have the phrase internally of the sea of sameness. We don’t wanna fall into that trap. So we really do try to differentiate ourselves right off the bat, and one of the ways that I do it is I like to drop off fudge, chocolate peanut butter fudge. And yes, it is something that I make myself. This is a recipe my mom’s been making for over 40 years, and I’ve been making it for seven and a half years. My tactic has changed over the years, pre-Highspot and post-Highspot, because before I didn’t have a good way of getting the information to the prospect about the recipe. But now I do. So what I have done is I have branded a QR code that takes the prospect to the recipe, and it’s housed in Highspot. So I can see who and when they click it. If I wanted to make it unique URLs, I could do that. But also, I can see when they’re accessing it, and then for how long they looked at it. So when I go to drop it, and number one, I always drop to the receptionist as well as to the prospect, before I get to my truck, I get an email saying that recipe has been scanned. I feel like I’m gonna be getting at least some sort of phone call back or return email for me to be able to have that additional conversation. Not having a tool like Highspot, I couldn’t do that before. It wasn’t nearly as easy. Now it’s a plug-and-play thing, and I’m rocking and rolling with it week in and week out. RR: I still can’t get over that approach. It’s so good, and it is so unique. I can’t imagine that there is anybody else that does that, and that is exactly why you get out to the parking lot, and already you’ve got someone on the line going, “Who is this?” Or, “You know what? I’ll take a call.” So I love that strategy. And I also love the call out to engagement data, of how you’re using that to intuit what’s happening in the mind of your buyer or in the mind of your prospect. So when a buyer engages with something that you’ve sent them, whether that is a fudge recipe or a brochure or whatever the case may be, what does that tell you? And then how do you use that to decide what to do next in a deal? TD: Number one, all I’m looking for is them to engage. Whether they like the fudge, they don’t like the fudge, they’re diabetic, or whatever the case may be, it sparks a conversation, and I’ve actually changed my process with that over the years. I used to drop the fudge, and then I would say, “If you want the recipe, just email me.” Well, no one willingly emails a sales rep. So it is definitely one of those things where I had to adjust. Now I can do my outreach. I can call, I can email, I can even text if I do have a cell phone number or something like that. And number one, I just wanna make sure they got it. Did they enjoy it? And then number two, if I find out too, because I’ve gotten this before, “Oh, sorry, I’m allergic. I can’t have peanuts or anything like that,” well, now I’m coming with one of the other drops that I have that is not food related. It gives me access and ability to have a conversation, be unique from the jump, and then after that, that’s when we bring in Digital Rooms or a brochure that we have tied to Highspot or something like that, where then I can interact with them in a more professional manner, talking about the products and services that we offer. It gives me the ability to adjust on the fly and do it from my phone if I need to, do it from a computer or an iPad, and it gives me the flexibility to build something specific for them. It’s not just the generic everyone gets the same response, and hopefully something sticks. I can have that personalization that you talked about at the beginning of the episode. RR: I love that, and I’m really curious too. So we’ve heard a little bit of the individual approach, of the very unique thing that you do, because I can’t imagine that every single rep at Paylocity is roaming around the continental US with fudge in their truck. Molly, I’d love if you could tell me a little bit about how you’re thinking about doing this at scale. What does your process look like for building something that you think, A, sellers will use, and that, B, buyers will go, “Hmm, maybe I should actually look into that”? MD: And one of the great things about Paylocity is our sales reps are gritty. And like Tommy was hinting at earlier, he tested the fudge approach. It’s the same with the Digital Room templates that we build. We know that when we put a Digital Room template out there, our re

According to Salesforce’s State of Sales Report, sales teams use an average of 10 tools to close a deal, which then leaves 66% of reps to say that they’re overwhelmed by the sheer number of platforms they’re expected to juggle in their day-to-day. So when an enablement team goes to roll out new tools, reps more than likely just stop listening because it feels like it’s just another login that they’ll slowly stop opening over time. So how do you introduce something new without asking reps to change how they already work? Riley Rogers: Welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully. Here to discuss this topic is Ryan Costello, go-to-market senior enablement tools specialist at Enverus. Ryan, thank you so much for joining us today. I’m super excited to have you here. As we’re jumping into this topic, and a little bit of a loaded one, could you kick us off just by telling us a little bit about yourself, your background, and your role? Ryan Costello: Thanks for having me, Riley. So I’m Ryan Costello, coming to you from Indianapolis, Indiana. I started my professional career as a high school English teacher. I taught for 18 years, and then I left the classroom. I spent a couple years as a learning consultant at Lessonly and Seismic, and for the last two or three years, I’ve been working at Enverus. We’re an energy technology company, and I’ve been on our sales success team, helping our reps use the tools they’re asked to use more efficiently. So I manage our content and learning management systems, as well as our call recording and social selling softwares. That’s the quick version of me. RR: So sounds like you’re the right person to talk to when it comes to tool adoption and long-term tool adoption. As we’re thinking about how you’re making that happen in the specific environment that you’re working in, I’d love to get a little bit of background on the challenges that you’re coming up against. So what is it that makes your go-to-market motion complex, and how are you trying to solve these challenges or simplify these challenges with tools? RC: Enverus is a company that helps all fields in the energy industry. So that means that we are helping solar companies, oil and gas companies. We’re helping people that are investing in new energy technologies. And so there are so many different fields within the energy industry, and we have hundreds of products and SKUs that sometimes overlap with those various segments, that it can become a real challenge to get all of that information to the right reps. And so what we’re trying to do when it comes to helping them leverage tools is making sure that as we continue to offer more and more for our customers, we want to make sure that as that haystack grows, their ability to find the needle, to find the piece of content they need, or the training to get better at selling, doesn’t take away from their time with customers. That’s really what we’re ultimately focused on. RR: As you’re, again, helping reps find the needle in the ever-expanding haystack, it does sound like there are many avenues through which your sellers, your sales managers, anybody who’s looking for information can go try to access it from the bajillion platforms that we all have. So where do your teams today work from? RC: First and foremost, we’ve had Highspot for years, and our organization is really comfortable with it. The reps understand its value, but they’re often in other platforms. So one example I’ll use is, they’re in Salesforce a lot. And so for a while now, we have incorporated a Highspot widget in Salesforce so that they can search for content from that platform, and many of them have grown accustomed to it because they just, for whatever reason, live in Salesforce more. But like everybody else right now, companies, including ours, are starting to give them access to AI platforms. And so our entire go-to-market organization right now is in ChatGPT, and then our sales leaders and marketing, my team, is also in Claude. So when I’m primarily serving the reps, the main need that we found was that the reps are being told, “Use ChatGPT.” And so what we found was they were spending more time in a platform like ChatGPT. So to have an option where Highspot could essentially follow them there, any opportunity we have for Highspot to be where they’re naturally at is something that we’re interested in. When they were spending more and more time in ChatGPT, we needed something that let them more easily get to Highspot without having to travel there, basically. RR: So since you’ve started using the Highspot MCP Server to, like you said, bring Highspot along with you wherever your teams are working, whether that is Claude, whether that’s ChatGPT, what kind of use cases are you seeing sellers using that for? And maybe what kind of use cases were they trying to use these tools for previously that were kind of difficult because they didn’t have enough context to really deliver them? RC: One thing that they’ve really enjoyed within the platform is that now you can use the search bar and ask it a question, and it’ll give you an AI-generated response, and you can have that conversational experience. They were still saying, “Yeah, but I need to combine the information on our products that we have in Highspot with the information that I’m getting from a call transcript with a customer or some information in email correspondence that I’ve had with them.” And so what we’ve started to see with the Highspot MCP and ChatGPT is the ability to combine the information in Highspot with the capabilities that exist outside of the platform. But by having Highspot present in ChatGPT through the MCP connector, they’re able to do things without jumping around and having to manually synthesize it themselves. RR: I know you spent a lot of time testing it yourself before you launched it out to the field to make sure this was something valuable, something they would use, something that fit into their workflow. Can you walk me through what the process of evaluating this looked like? RC: When it became available, we met with our Highspot CSM and a Highspot TAM to talk through what the MCP was designed to do. And before I wanted to have our reps try it out, I wanted to make sure that it would serve their needs. And so the Highspot team gave me a whole set of sample scenarios. Here are the types of questions that we think reps would be served by. And I took quite a bit of time. I tested every sample prompt, every scenario that Highspot gave me. So I took the time to see, are the prompts and scenarios that Highspot has designed this MCP to help with, are they landing with the content that we happen to have? That was a really important process because I certainly identified some prompts and scenarios that just because of the nature of our business, didn’t quite land. So that was the first step, was let me try these out and see what lands and what doesn’t land, so that I could identify what to unveil this with to ensure that the first time a user tries it, it hits. So that testing allowed me to prepare resources that would lead with what it’s best at and give some troubleshooting right off the bat so that if they stub their toe, they had a quick solution. So that was all just the testing phase to then get to resources so that I could create a how-to video and a how-to guide so that they could step by step set it up and try it out. RR: To the point at the top, you launch a tool, it sounds scary, nobody uses it. If you can make it easy, or at least feel digestible, you give yourself a little bit of an edge. So I’d be curious, in addition to the resources that you built and the thoughtfulness with which you approached what works, I’d love to know a little bit more about what the rollout to your teams looked like. RC: So after I had tested everything, we did what I would consider a soft launch. We let all of our Highspot users know that it was available, and we designed those resources so that whether they were using ChatGPT or Claude, the resources focused more on what the Highspot MCP could do regardless of the platform. All the information was essentially the same so that we didn’t have to create two different versions of everything. But once we had tested and had those general resources, we let everybody know via email and our Teams channels, “This is now available. Try it out.” And that probably lasted a month and a half. And while that was happening, I was asking, “If anybody’s trying this and you’re having success or not, let me know.” Because before we did a full rollout, I needed to know the real-world application and value of the MCP, which I just can’t do myself because I’m not a rep and I’m not talking to customers. And so during that soft launch, our reps who were always up to try something new, they were our guinea pigs, so that when we did a full launch about a month and a half later, I could have more specific use cases. And so the full launch had resources that were more specific to us, and I was just more aggressive. So we again fully launched through email and Teams channel communication. And then every week, I would provide specific examples from our guinea pigs earlier, knowing that it had genuinely helped them, and that would ultimately give this more credence. And so for the last month and a half or so, that’s what’s been happening. Every week, I post new updates, I continue to ask for feedback. It’s amazing the motivation a ten dollar Starbucks card will get in people responding to surveys. And during all that time I’ve been able to continue to fine-tune

According to Gartner, worldwide AI spending is forecasted to increase 44% by the end of 2026. Companies are investing in AI, and they are investing heavily. But knowing where and how to invest isn’t easy, especially with what feels like a million different AI tools out there and a million more different ways to build your own. So how do you figure out what to build, what to buy, and which investments will help you move the needle for your business? Riley Rogers: Hi, and welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully. Here to discuss this topic is Cody Sims, head of commercial brand at Cox Communications. Cody, thank you so much for joining us today. Super excited to hear your thoughts on this one. Before we dive into what is quite a loaded topic, could you tell us a little bit about yourself, your background, and your role? Cody Sims: Yeah. So, hi, I’m Cody. I’m the head of commercial brand for Cox Communications, and it’s kind of crazy how I came into this role. So I actually started my career when I was 15 and was installing phone systems for my dad’s phone company. And after that, I had actually had two parts of what I thought was what I wanted to go into, and that was either musical theater or physics, because those were two things I really had a passion about. And when I got into college and had musical theater as my major and physics as my fallback, I realized that both of them left a part out of what I really enjoy. And so I ended up actually landing in marketing because it’s both analytical and creative, and that has served me really well over the years. So, across Cox, I have done all kinds of things from product management to market development to pricing to competitive analysis, and now in the brand world. It’s given me kind of a 360 view of the entire business from a marketing lens. I would say that I’m pretty much a transformation leader. I really enjoy breaking things and building them up new again. So, AI is happening right at the right time for me. RR: I love that story, and I love that it’s taking you to a place that especially now is getting more and more technical, more and more analytical. I’m very excited to get into that transformation leader side of things. But before we do, can you paint a little bit of a picture of your sales environment? CS: Yeah. So when I first came to Cox, it was very similar to most of what you would call a CLEC, or a competitive local exchange carrier, which is primarily internet service, voice services, and obviously because it was Cox, some cable TV services that were the triple threat. That was kind of what in the early 2000s was kind of the way that they went to market. But over time, the team at Cox realized that in order to stay competitive, they had to add to the portfolio to make sure that they were providing value to their customers, and I’m sure many would understand that and have gone through similar transformations. And so we had acquired several different other companies that added to our portfolio, and developed some of our own products, and over time that turned into a lot of products. But it’s not just 70 products. It’s 70 products, it’s nine customer segments that we have from a segmentation perspective. It’s six distinct buyer personas, industry verticals, what’s serviceable at that address. So you take all of these different components and it’s almost like three-dimensional chess for the salesperson. The way that I like to think about it is that the sellers, what they really need and what their challenge is, is that they’re not looking for specs. They’re looking for what are the business outcomes that my customer is trying to achieve, and then what do I have from my portfolio that will help them to achieve those results? So it’s no longer a world where they can memorize everything and know every product in and out, and be the technical expert. They really do have to have tools and systems that help them to have the right knowledge at the right moment for the right person in the right place. RR: Yeah, there comes a point when the human brain just can’t contain the context and the expertise that you need. So when you can’t ask for expertise, what you can do is provide, to your point, that just-in-time support. And one of the things that you alluded to was that that’s where you kind of started some of that AI investment as a way to bridge that gap. You’ve given us a little bit of a taste, but what kind of motivated that early initiative? CS: Well, I would say that, over time what we discovered was that we couldn’t keep track of all of our marketing materials, collateral, all of the pieces of information in just files, formats, and putting it online into a here’s-an-accessible-library. Because the library just becomes bigger and larger and more difficult to manage. But I would say that we didn’t set out to do AI. We didn’t sit down and say, “Oh, hey, AI looks cool. Let’s make sure we’re doing it.” We needed to transform our go-to-market strategy so that we were more nimble, we were more competitive, and that we could deliver the kind of experience that our customers were asking for. And so AI was the mechanism that would help us to get there. But what really triggered this whole thing was what I mentioned earlier, was our segmentation. When we sat down and said, “Let’s rebuild the way that we look at our audience segments,” and we did that based off of what is the value to Cox of each of these customer profiles, and then what is the technology sophistication of that client, of that business. And that intersection allowed us to create our nine different segments that we were working on. And so when we did the math, when we looked at all of that information and all of the things that we needed to be able to provide to those segments, we realized this was quickly going to turn into something that was far beyond any marketer’s ability to do. But what we knew is that the Gartner information we were tracking said that personalization was having much higher returns on the way that people respond to information. And not only that, but if you do personalization and you get it wrong, if I call you and I say, instead of, “Hey, Riley,” and I say, “Hey, Jonah,” you’re like, “Hmm, nice try.” So personalization is really important to being successful, but getting it right is even more important. So we realized that we needed to have some radical partnership between our marketing, AI, and sales teams, that we needed to make sure that this was not just an IT project, that we were going to go and pull a bunch of requirements together and everybody would be like, “Oh, hey, here’s this new tool. Everybody figure out how to use it.” And it wasn’t necessarily about optimization. It was about transformation, the way that we go to market, the way we think about our customers, and the way we show up. So I would say that AI definitely was part of the solution set, but we had to look ourselves in the mirror and say, “It’s time for us to actually think about this in a completely different way.” RR: That distinction comes through very well, and I think is very important because oftentimes when you’re in kind of the scramble to be keeping up with the market, keeping up with your competitors, there is this urge to just tack on AI because we have to. But when it’s not strategic and it’s not built into the things that you’re actually doing, to your point, it’s we put together some specs, good luck using it. But instead, now it’s something that’s really built into the way that you work. I would love to hear a little bit more about that specific use case, especially given the fact that a lot of teams are running into that question of how do we use AI and can we just build what we need ourselves? Given that you’ve done the math, answered the question, I’d love to hear how it worked and kind of where you landed. CS: It’s very easy to fall into the trap of, “Hey, everybody, here’s AI. We put it on your computers, now go use it.” And so then everybody starts using AI to try to figure out, how does this help me in the job that I already do, in the role that I already do, in the processes that I already do? And so then it really limits the impact that it can have on the business and the performance because either, A, you have a handful of people who are really smart, and they go crazy with it, and they create their own thing, or you have a bunch of people who are looking at it going, “Okay, came up with some ideas, but I still have to do my work.” What you end up with is there’s no standard. There’s no flag running up the hill to say, “Everybody follow me. Let’s go do it this way.” So, it required both the yes, we had to make sure that the teams were bought into using AI, but we also had to have a standardized way of approaching how we deploy AI. And that brought us to the question of do we buy or do we build? And because there were so many different parts of what kinds of functionality we needed, it wasn’t the same answer for every one of those needs. So in some cases, we have a tool, we have a partner, they already have AI integrated into their platform, let’s go see how we can use that. In other cases, and I’ll give you an example, in the case of content generation, that is where we started with our AI journey about a year ago. We sat down and started interviewing and reviewing all of the different providers who can do content generation. Every one of them had a different approach to content development, content generation, which were all very good, and they attempt to make sure that they are covering as

According to research by Gartner, by 2029, sales organizations with AI-driven enablement functions will achieve 40% faster sales stage velocity than those using more traditional approaches. But getting there means building the kind of workflows that tell you what actually works, which is only possible when you can see inside the conversations that selling actually happens in. If you can’t, you might just find yourself scaling an AI-powered program that’s completely misaligned with how your sellers sell and how your buyers buy. So how do you understand what your teams need, and then build an innovative, mature, AI-powered enablement program to match? Riley Rogers: Welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully. Here to discuss this topic is Jill Sawyer, Director of Sales Enablement at RL Datix. Thank you so much for joining us today, Jill. I’m really excited to have you here. I think we’ve got a very fun conversation ahead. Could you give us a little bit of an overview of who you are, what your background is, and your work today? Jill Sawyer: Yeah, absolutely. First, thanks so much for having me. I’m super excited to be here. Currently, I sit as the Director of Sales Enablement for North America at RL Datix. I’ve been here for a little over seven and a half years. JS: My background is a bit non-traditional for sales enablement. I started more on the marketing and product marketing side. I moved into the enablement role a few years ago, a little bit over two and a half years ago, but I was really stepping into a function that needed to be built from the ground up. That meant figuring out not just what sellers needed to know, but how to help them actually use it in moments that matter. I’ve also recently gone back to school. I’m currently pursuing my Master’s of Jurisprudence in Health Law at Loyola University Chicago, which has been really valuable in this role. Our customers operate in a highly regulated healthcare environment, so understanding more about compliance, patient safety, risk, and legal frameworks helps me think differently about what our sellers need to understand and how we support them. RR: And you wear so many hats through it all. I’m really excited to see how all of this comes into play in your work today. But before we jump into what you’re working on now, could you give us a little bit of an overview of your sales environment? JS: Yeah. So the way I usually describe RL Datix is that we sit at an intersection of healthcare safety, risk compliance, and operational reliability. Our customers are health systems and hospitals that are trying to solve problems with very real stakes. They’re trying to either prevent harm, respond appropriately when something does go wrong, or maintain regulatory readiness. So it makes our sales environment really complex because those problems rarely belong to one department or one singular buyer. The buying committee can be really broad, and each stakeholder is looking at the problem through a different lens. So for our sellers, the challenge is being able to zoom in and zoom out. They need to understand specific workflows, not only within our product, but within the landscape. But they also need to connect that workflow to the larger operational and strategic priorities of our customers. This is where enablement for us becomes really important. I’m helping translate complex healthcare problems into clear, relevant conversations about value and outcomes and how RL Datix helps raise the standard of care. RR: So a lot for sellers to juggle, and a lot for you to help them juggle, especially because you built the enablement function largely from scratch. While doing so, you were learning what sales enablement as a concept is, what the function should look like, and how you should tailor it to your specific environment. So how did coming in without a more traditional enablement background change the way you thought about what to build, and was that kind of an advantage? JS: Yeah, so I think coming in without a traditional enablement background shaped our function in a really positive way. Since I’ve come from marketing and product marketing, I was always really thinking about our audience, message, positioning, and customer value. But when I moved over into enablement, I quickly realized that having the right message or right content was only part of the equation. I needed to help our field know how to use it in real customer conversations. I really came in thinking about what my sales reps actually need to be more confident, more consistent, and ultimately more effective. Of course, sellers needed content, but they also needed guidance, learning, reinforcement. Our leaders needed coaching and better visibility into what was working and what wasn’t. So in some ways, I approached enablement like building a product. My sellers were the users, the sales process was our workflow, and it was my job to understand their friction points and build them something that made it easier to have stronger customer conversations. RR: I love that. It’s enablement, but make it product marketing. You listed out some things that were important for sellers and things that were important for your leaders, and all of this you had to build from scratch. So as you were looking across what needed to happen, what your first few check boxes on the to-do list were, a key first step was assessing what you had and what you needed. How had RL Datix been supporting its sellers, and where did you start to see those first few gaps? JS: Yeah. When I first stepped into the role, we had a lot of strong subject matter expertise and a ton of people supporting the field in a variety of different ways. The issue wasn’t that our support structure didn’t exist, it was that it wasn’t really connected or, quite frankly, easy to scale. I had a lot of content, but it lived in a variety of different places. We had trainings, but much of it was event-based or dependent on live sessions and then going back and watching re-recordings. I needed to make sure my sellers were hearing the same message and had access to the same guidance on how we wanted our customers to hear about RL Datix and our offerings. And I needed visibility, not only for enablement, but for collaborative teams like product marketing and product, into what was actually being used, what was resonating with our customers, and where we still needed to support the field. So my final assessment really shaped the foundation that we built. It was truly creating what I call that connected enablement environment that could support sellers in the flow of their day-to-day work. RR: Yeah, and I think a recurring theme through all of this is that there were levers to pull, content to create, training to centralize, all of these things, but that wasn’t the end goal. The end goal was that when a seller hits the field, when a seller is on a Zoom call, they’re saying the right things, and they’re not just reading off bullets, they’re tailoring it because they know it and they know it well. So you’re looking at what you need to do. You have your content, you’re beginning to get it centralized and organized, your training is in place, you have data on what reps are using, you’re building. But you still can’t see inside the conversations that sellers are having to understand whether all of that work is, for lack of a better word, working. So what challenges did that lack of visibility create, and why did you start thinking that maybe a conversational intelligence tool was that next step forward? JS: Yeah. So when we brought Highspot in, we truly started with a baseline foundation. Before I could do anything more advanced, I needed to, step one, make it easier for sellers to just find what they needed and understand how to use it. It may sound really basic, but it was a huge step forward because it helped us connect content to the way sellers were actually selling. It also gave us a huge level of visibility. I could start to see what reps were using and what they were not using, to identify those true gaps. But the missing piece was actually our customer conversations. I could easily know if a rep opened a deck or completed a course, but I still didn’t know how that translated when they were in front of a customer. Were they asking strong discovery questions? Were they connecting the message to the customer’s priorities? How were we handling objections? What were we hearing? Without that level of visibility, there was still a lot of guesswork. Enablement, product marketing, product, and sales leaders were all trying to support the field, but a lot of times we were relying on anecdotal feedback or even secondhand information. Conversational intelligence really helped close that gap, and that foundation is really what made the next phase possible. Once we had the content, the training, and guidance all in one spot, I could start to think about how to layer other pieces in, like coaching, conversational intelligence, and eventually deal-level insights on top of it. RR: When you first had that line of sight into the field and what they were actually coming up against, was there anything that you didn’t expect that came through? Things that sellers were either saying that you were like, “Oh my gosh, have you been saying this for the last umpteen months?” Or that you had no idea they were running into that was a problem. You were like, “Oh, we should’ve been helping with this,” or, “We could be enabling differently.” JS: Yeah. I think for us, what it really helped open up was just the level of content that I needed. We had really great high-level intro, top-of-funn

According to Salesforce, sales professionals spend up to 40% of their time searching for the information and knowledge they need to do their jobs. For go-to-market teams stretched across multiple products, multiple acquired businesses, and a sprawling tech stack, that number can feel like a conservative estimate. So how does a solo enabler cut through the chaos and build something an entire go-to-market organization actually uses and actually trusts? Riley Rogers: Hi, and welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully. Here to discuss this topic is Heather Darling, senior sales learning and development manager at HSI. Thanks so much for joining us today, Heather. Super excited to have you here. Wondering if you can kick us off and just tell us a little bit about yourself, your background, and your role. Heather Darling: Yeah, absolutely, and thank you so much for having me, Riley. Appreciate it. My background actually started on the customer side. I spent a few years in customer success at HSI, working directly with our customers, building relationships, identifying growth opportunities, and helping them drive product adoption. So over time, I realized I really loved helping teams get better at that work and not just doing it myself. So I got my master’s, and I moved into the sales learning and development role, where I now design onboarding and ongoing learning for our sales reps and CSMs. And a big focus for me is practical application, so I spend a lot of time building programs around how to position our solutions with buyers, how to teach reps about our solutions without overwhelming them with information that they don’t need. Recently, I’ve been focusing on how AI can help sales teams show up more strategically with customers, so I’m really focused on how you turn enablement into something that actually changes behavior. And because I came from customer success, I think a lot about the full customer life cycle. So a lot of my work is in helping teams connect the dots across sales, onboarding, and long-term success. In enablement, I just think it’s important to focus beyond training and think about how we build a culture where people are continuously improving. RR: Your intro tells me we’re going to have a great conversation about how you’re bringing all of that to life. But before we do, I’d love if you could maybe give us just a little high-level view of HSI, just so we have a little bit of a framework as we’re going into the conversation. HD: HSI is a workplace safety training and compliance company in the environmental health and safety space. Ultimately, our goal is to help companies operate safer, smarter, and with less complexity. So we sell to SMB and enterprise organizations across a wide range of industries. Within those companies, our buyers are typically EHS leaders, HR and L&D teams, and operations leaders. So basically anyone who’s responsible for tracking workforce performance, compliance, and risk. RR: Love it, and that is, to your point, just about every company aims to do that, so broad customer base to serve, broad prospect base to target. One thing that you mentioned to me when we spoke last was that HSI’s growth has come from acquisition. So can you tell us a little bit about what’s challenging about working in an environment that’s constantly changing and trying to enable your teams through that change? HD: Honestly, it’s a tough environment to run enablement in. Growing through acquisition, you’re constantly dealing with new products, old branding, different messaging, new systems, and even different workplace cultures converging. So, it sometimes feels like nothing is ever fully standardized. You’re always evolving, working towards a moving target, and the teams are always needing to absorb new information. So you’re trying to help reps understand what to sell, how it fits together, and how to tell a simple story even when the business itself is still getting aligned. On top of that, priorities are shifting with a moment’s notice, products are getting rebranded, positioning is evolving. So enablement needs to stay really plugged into the business and be flexible. There’s long periods of waiting to bring a new product to market sometimes, and then suddenly it’s go time, and you need to be ready, and you have to get everyone else ready. At the end of the day, it’s just a balance between driving consistency and accepting that some level of change is always gonna be your reality. So if you wanna be successful without driving yourself crazy, you work to have a structure in place to bring consistency to your own role in those moments. RR: I would love to know what your personal process for creating consistency amid that chaos is. I think that’s something that’s often challenging to do. HD: That’s a good question. I spend a lot of time meeting with our leaders. I touch base with them at least once a month. I go to team meetings when I can. I just try to stay as plugged in as possible to all the different things that are happening within the organization. For me personally too, I have a mission, vision, and values for my team of one, and so it’s a touchstone for me to go back to. Like, “Hey, am I meeting the goals and the principles that I’ve set out for myself?” Make sure that we’re doing the things that are not out of scope, but also that we are doing the things that we need to be doing to address what’s happening at the moment. RR: I think that’s one of the things that’s really hard, and something that when you talk to solo enablers is probably one of the hardest things, is that wherever you are, enablement is a game of change. It’s a never ending project. There’s always new things for people to learn, always new things for people to do. But when it is just you, and when things are changing fast, staying true to those north stars and that scope that you’ve set, beginning of the year, beginning of fiscal, gets hard. So I really appreciate those tips for how to maintain structure, how to not go crazy, and how to keep yourself on a path that supports your work and the business. So thank you for that. You alluded to a little bit of this in your introduction. Acquisitions aren’t easy. They add new product lines, they add new collateral, they add all sorts of different branding, messaging, et cetera. So what are you seeing that cause for reps? HD: For reps, I think the biggest challenge is just suddenly they’ve got a bigger portfolio of things that they can sell, but it’s not always clear how the pieces fit together, what they need to lead with. If you’re not on top of that as an organization, rep’s confidence drops, your sales cycles get longer. You tend to see people fall back on doing and selling what they already know. People can be reluctant to bring up a new solution that they might feel like they don’t fully understand. And so again, I think that’s where it’s really important to make sure all those pieces are in place as much as possible before you bring the reps in, because they don’t fully understand something, they don’t feel confident in talking about it, so sometimes those new solutions, they don’t get brought up as much as they should. That’s definitely a challenge. For the broader go-to-market team, it creates a lot of inconsistency too. We’ve got different messaging, different positioning, overlapping collateral. It’s really easy for marketing, sales, and customer success to get slightly out of sync, and that shows up pretty quickly in the customer experience. Your risk really with that is not a lack of resources, it’s almost in having too many. It makes it hard for people to find or trust what’s relevant. So you might have reps sharing old collateral with legacy branding because they feel comfortable, they feel like that’s something that they trust. They’re measured on results, so when something is working for them, they don’t wanna risk messing that up. And so change can feel like it really slows them down or it puts deals at risk. So when you’re introducing new products, new positioning, or new tools, especially all at once, that can create some hesitation. Reps are gonna tend to default back to what they know, what they trust, what they’re comfortable talking about. RR: Hearing all of those challenges and also some of those questions that you asked, when there are so many priorities swirling around, so many new things coming in, how do you find that clarity, and how do you create that clarity? And I think one of the things that you shared was an answer to that was, “We needed some tooling.” And so you started looking for some tools to help with that, that problem of reps don’t feel confident with our new solutions. And so I think you were looking initially maybe for something more aligned to an onboarding tool, and then you wound up here with a sales enablement platform. HD: Yeah. Yeah, it was an interesting shift because early on I really was thinking about this as an onboarding problem. So how do we get new reps ramped faster, especially with how complex our business has become? But as I got deeper into it, I realized that the bigger issue wasn’t just onboarding, it’s ongoing development, coaching, creating and tracking certifications. So the challenge doesn’t stop after those first 30, 60, or 90 days. The business is still changing. We’re adding new products all the time, messaging keeps evolving, and that can be really a struggle for reps to keep up with. So there’s just so much information coming at them about buyers and products, and not to mention our internal processes that can sometimes

According to Gartner, at least 30% of generative AI projects will be abandoned after proof of concept due to escalating costs, poor data quality, or unclear business value. There are a lot of factors working against them, and too often failure happens when teams are right in the middle of building. They’ve spent significant time, money, IT capacity on something that may very well have been doomed from the start. So how do you know if something is actually worth building with AI or if you should just focus on buying instead? Riley Rogers: Hi, and welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully. Here to discuss this topic is Keith Weaver, Senior Director of Global IT and Enterprise Applications at Highspot. Thanks so much for joining us today, Keith. I’d love if you could just kick us off by telling us a little bit about yourself, your background, and your role. Keith Weaver: I have been leading our global IT team at Highspot. I’ve been in IT for, I think, getting close to 20 years now, just overseeing all kinds of different systems and specialties within those systems. Our IT team at Highspot is IT operations, making sure everyone has devices, equipment, all of that globally. We’re now in seven countries. As well as system engineering, making sure everyone has the right tools, that they’re optimized for the business. And then we have specific teams in IT that specialize in financial systems and HR systems. In the world of AI, it’s a whole new world and it’s a lot of fun. RR: So 20 years in IT, you’ve kind of run the gamut. But it sounds like the last two and a half years have crammed almost 20 years’ worth of change into a very short window. When we were planning for this episode, you mentioned to me that you read four or five newsletters every morning just to keep up with the pace of innovation. Can you walk us through why you’re spending so much time learning and how IT has had to evolve to keep up with this pace of development? KW: What I’ve seen is mostly it’s the same things that we’ve done, except it’s done at a much faster pace. It is kind of an unheard of pace that AI is moving. Every day, the reason I read five different newsletters is because there are so many new things getting released, whether it’s a new model or a new tool, and then there are things within the tools that are getting released. Trying to understand all those things, the new protocols that are getting released, the new ways people are building or executing on AI, or the new things people are learning, is just really critical. And all of that is at a speed that we’re just not accustomed to. So I think that the objective of what an IT team does to continue to keep the business unlocked, able to do their best work with the technology and tools while making it secure and scalable, those things are the same. It’s just the speed now that it’s running, and the speed from the business. The business is moving so fast, and their expectation is that IT continues to deliver at that pace. I’ll give you some examples. I get probably, me personally, not my team, but me personally, I probably get 20 to 50 requests for new connections, new skills, new tools every week. That’s in Slack, in Jira. It’s just nonstop, and that’s just unheard of before AI. It just didn’t happen. It would be like, “Oh, we have this big initiative, and we’re gonna do this thing.” And now it’s just like, “Can I have this? Can I have that?” And all good things, it’s just how do we do that, and how do we keep up? RR: So when you have 20 to 50 requests hitting your desk every week, it can probably start to feel a little overwhelming. And I wonder if the folks who are sending these requests your way maybe don’t know the considerations behind every single one of these ideas. I’d love if you could give us a view of what you’re seeing across the industry as both technical and non-technical teams are all noodling on the idea of how to build with AI, how to buy AI tools, how to bring them all together and create a combination that actually works. What are you seeing? KW: Well, I think if you think back a year to a year and a half ago, mostly people were buying tools. Building was… It’s so funny ’cause we’re talking about a year ago or a year and a half ago, but building was much harder. And really with Claude, the Opus class models that came out, it really started unlocking the ability for everyone to start building. And so since then, the conversation shifted from, “Yeah, we can go buy this tool,” to “We can build this internally.” And there’s a lot of excitement to build because building’s fun. The pendulum just swings often on these things, and so we’re kind of in that wave where everyone’s super excited about building something. And I think we’ll end up in a place that is more normalized, where we’re building some, we’re buying some. We’re doing a hybrid approach. I think that is where we’ll end up. It’s just, it has swung really far to, “Look, we can just go build that thing.” RR: So it sounds like we’re kind of in the early phase of a cycle that you’ve seen time and time again, where surrounded by enthusiasm, but maybe we don’t have much direction. And like you said, building is fun, so I imagine you probably hear a lot of, “Hey, look what I built,” or, “Why can’t we just build this?” So when something like that lands in your inbox, what’s the first thing that goes through your mind? KW: If it’s, “Look what I built,” there’s lots of questions, like how is it being deployed? What’s the next step with this? Who’s gonna own it? How is this actually out in the world, and how are we gonna make sure that it’s as scalable and secure? If it’s a conversation, I would say this is more so where we hear, “We want to build this thing,” or, “We can just go build this thing. Why would we buy this?” I think the thing that I would ask is, what is the long-term path for this? Because deploying is just the first step. It’s the iteration. It’s the test. It’s continuing to deploy it. It’s maintaining it. It’s supporting it. It’s the full life cycle of any software project. What resources are gonna do that? How are we going to maintain this and support this long term? Those are usually the questions that I start asking. RR: And you’re quite equipped to speak to the build side of the equation because you’ve done it. You’ve tackled the planning, the deployment, the maintenance, the ongoing support, the full life cycle, like you said, of a software project. And you’ve done it with AI. I’d love if you could walk us through your first test case. Tell us a little bit about what you were thinking going in, and what you learned along the way about what works, what doesn’t, and what was surprisingly difficult. KW: Yeah. So we built an IT AI agent and an HR agent, and we did that with a cross-collaborative team. I think we started it last fall and then deployed it in February or March this year. And I would say the main objective there was not that these are the tools that are gonna change the way we function. The main objective was a learning. It was an R&D investment. So we knew that we had to, as an IT team, be able to help the business deploy these agents, and we found some use cases that we could. The IT one we can own in-house. The HR one, we already collaborate with them very closely on a number of things. So it felt like a good first step for us to dip our toes, learn a lot about how to build these, what works, what doesn’t. And these agents are more than just chatbots. They really were taking actions in tools like Jira and Workday, Highspot itself. And we built them using the Workato platform, and what we learned through it is it was actually really exciting and really easy to get to a place where this mostly works, and this is pretty, it feels like this could be really powerful. That was, like, the first three weeks. The rest of the time was, “Oh, gosh, how are we going to get this thing so that it doesn’t give somebody some really poor answer from a security standpoint or an HR answer that needs to be rooted in truth?” And then how can we make sure that it repeatedly does these actions no matter what people prompt, that it’s really controlled? I often described it to my team like it was training a four-year-old. I have four kids and they’re all older now, but it was like I was back in those toddler stages. Like, “Why’d you decide to do that? That was a bad decision. Stop.” And trying to train it and get it to that point, it just took a massive amount of time. And since we’ve launched it, it’s a lot of resources to read the conversation, understand what was asked, understand what it did and where it went wrong, then refining it, then retesting it, then redeploying it. It’s a cycle. It’s this continual cycle, and that takes a lot more resources and time than I originally thought it would. RR: Ballpark, what did that investment look like? How long did it take you to build? How many queries did you have to manually validate before you trusted the thing? And how much are you still investing today to keep it alive? KW: In the beginning, you just start giving it manual prompts and testing it to see what it does. Then you produce your test cases, and you manually go through those test cases, and every time you make some major changes, you go through those test cases, make sure that it’s still hitting. Because just changing one little thing, for example, if you take a tool and change the prompt or the description of that tool, you actually have to do regression testing on all the t

According to research by IBM, just 16% of AI initiatives have achieved scale. Why? Because few organizations have the structure and data to support long-term AI investments. So, how do you build an AI-ready system? Riley Rogers: Welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully. Here to discuss this topic is Rich Weymer, Senior Director of Go-To-Market Strategy and Transformation at Yubico. Thank you so much for joining us today, Rich. I’m super excited to have you here to dig into all the expertise that you’re gonna bring to the table. As we’re kicking off, I’d love if you could just tell us a little bit about yourself, your background, and your role. Rich Weymer: Yeah. First off, thanks for having me. A repeat customer with Highspot, so excited to get invited to this, as we’ve worked with your organization for some time now. Like you said, Rich Weymer. I’ve spent time pretty much so in tech for most of my professional career in one form or fashion, from my earlier career days at Microsoft working in consumer goods, where I’ve worked on video games, your Office products, all your devices, through where I’m at today in the security world. RR: Well, amazing, and bravo, tech veteran. Not easy. RW: Yeah. It looks a lot different today than it did when I started, that’s for sure. RR: And I think that is exactly what we’re gonna talk about today. But before we go into where the world of tech has been to where we are today, I’d love if you could give us a little bit of foundational context for folks who might not be familiar with Yubico. Could you give us a little walkthrough of who your company is, what you do, who you serve? RW: Yeah. So Yubico does phishing resistance hardware MFA, which basically means we ship you a little bitty key that helps control access to all your online portals and logins and everything along those lines. RR: As somebody who is password challenged, I certainly see the value of that one. I wish we had a wonderful little bitty key that got me set up for success every single day. One thing that I think you set up early on is that Yubico, and pretty much every other organization in the industry, is moving fast, and it has to. Security in this day and age is harder than ever. And when it comes to working in a fast-moving organization, teams like yours also have to move fast. I’d guess that that pace of change is part of the reason why you have a really forward-looking approach to enablement and to go-to-market strategy. So why do you think it’s important to think critically about how technology can transform traditional workflows, processes that you’re accustomed to, things like that? RW: Again, to your point, things are moving so fast right now. That’s the biggest underlying factor that organizations really need to think through. Decisions that you’re making today are almost obsolete by the time you’re done signing the paperwork on whatever decisions or procurement you’re going through. So you need to be really thoughtful about the foundations that you’re building, the integrations that you’re gonna lean on, and the partners that you’re gonna select that are gonna be around for the long run. Measure twice, cut once, and also understand that there’s different types of decisions that you’re gonna be making. I use the analogy of a hat, a haircut, or a tattoo. What type of decision are you making when you’re thinking about your technologies? If it’s a hat, you can switch it in and out real quick. If it’s a haircut, maybe it takes a little bit of time to unwind. And those tattoos are the ones that you just can’t change. They’re gonna be– They’re– You’re gonna live with them forever. So you really gotta just understand the lens that you’re making the decisions through, as well as having an industry understanding of where things are heading. And as you look at your partners, thinking, “Hey, at the pace at which innovation is happening, is this someone that’s gonna be relevant six months, 12 months, 18 months from now?” RR: I have not heard that decision-making framework before, hat, haircut, tattoo. RW: It’s an easy one, yeah. A lot of organizations think everything’s a tattoo. So you make every decision like it’s the last decision you’re ever gonna make in that space. And it’s right for a lot of things, but framing it goes a long way, especially when you’re trying to move fast. Being able to categorize those decisions pretty quickly goes a long way. RR: Yeah. And it helps you avoid the problem of when everything’s important, nothing is. You mentioned systems, data, processes, having the right tools in place to move quickly. So with that perspective in mind, how are you thinking about layering on AI? RW: I think about it every day and night, in every meeting I’m sitting in, and every conversation I’m having, and every free minute when I’m thinking about work. The big thing is automation and AI for the sake of AI, and automation for the sake of automation, it really doesn’t mean anything unless you have a strong foundation and an understanding of your data. So to me, it all just boils down to a strong foundational data set and understanding what to measure and what moves your business, and then building around that first and foremost before you do anything else. RR: What do you need in that foundation before you can start building AI on top of it in order for those initiatives to be successful? RW: If I were to think through how I structure this, there’s no shortage of ways to measure the business, but landing on one that’s influential and helps you adjust the dials as you go is really important. So the way I operate is through the lens of sales velocity, which is a time-tested mathematical problem to give you a temperature check on how the business is doing. It’ll let you know whether you’re going up, down, left, right, staying center, or whatever it is. But where organizations stop is they stop at the top four measurements, which, if you think of sales velocity, is open opportunities, average deal size, win rate, and then you divide that by your deal cycle length. That gives you a daily throughput, which tells you part of the story because you can help understand your forecasting. When you take your close one business, you can use that to forecast days left in the quarter, what those numbers would look like. But where it gets really powerful, and what I think a lot of organizations haven’t spent the time to do, is go deeper on the leveling of those metrics. So if you think through the process lines, L1 is your executive metric. That’s the all-up number. Your L2s are your leadership numbers, where your managers need to understand those. But your L3, four, five, six, and you can keep going down the rabbit hole, really start impacting how your frontline folks operate. One of the things we’ll talk about today is AI Role Play, and when we think of it, we look at diagnosing issues in our win rates, and we think, “How is our competitive wins doing? What are we, we get very, very granular in how we look at those.” And then we can actually start layering on recommendations and automation. So we do that across probably close to 100 different metrics through the various layers that are our leading indicators. And this really helps us when we think through automation of where we go from here, ’cause once we understand those, we know how are we doing against certain competitors? Are we getting the right amount of MQLs? Are we talking about the right things? Do we get caught up in legal, security? We can understand all those different variables of the business, and then we can take a proactive approach to coaching where we need to coach, and then adjusting the business where we need to adjust the business. And you can’t really do that unless you have that entire foundation laid out and actually understand what all those levers are. So to me, taking the time to do that is really just beyond critical. RR: Yeah. Yeah. You know what you need to do, and you can start driving really aggressively against it, which I– it sounds like you alluded to an example there with AI Role Play, you’re doing the work to do. In that, you’re beginning to layer some of these new technologies, new tools on top of that foundation. What were some of those first use cases that you prioritized, and why did you start where you did? RW: I think the first win you always wanna go for is really a practical application of any new technology and how that can move the needle for the business. So when I think of practical applications, I think of AI Role Play as being a very early one. As an enablement team and a training team, how many times have people walked through certification programs, the one-on-ones with managers, all the Role Plays, all the back and forth and the headaches and the objectivity that goes into those exercises. That’s just a quick win that you can pick up and take care of almost all of that. The time saving alone and the cost of having a manager do these one-on-ones time and time again, it just drains an organization when every organization right now is trying to be lean, mean, focused on sales efficiency. So anything we can do to give back and level the team up, I think is just a no-brainer. So AI Role Play is a huge one for us. We looked at a lot of different places. We tried a lot of different things, and we landed on the Highspot implementation of that because it’s important to be able to do that stuff, but also it has to be within the context of everything you’re doing and all the content and everything that you do have. It can’t b

According to Corporate Visions, 74% of buyers say they faced too many competing options in their last major purchase decision, and instead of selecting a vendor, they just checked out entirely, gave up, and moved on. So, how do you create a buying experience that makes those decisions feel easy? Riley Rogers: Hi, and welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully.  Here to discuss this are senior enablement program manager Lisa Monahan and account executive Madison Leatham from Pluralsight. Thank you guys for joining us. I’m super excited to talk through this topic with you. I’d love to just hear a little bit about yourself, background, and role. So Lisa, wanna kick us off? Lisa Monahan: Yeah, absolutely. My name’s Lisa Monahan. I live in the suburbs of Austin, Texas, and I’ve been at Pluralsight two and a half years, and I’ve been in enablement for, I guess that’s coming up on four years now.  I currently serve our go-to-market tech stack from a strategy and execution standpoint, and that is where I learned about everything I know and love about Highspot. So big Highspot fangirl here. Happy to be here. RR: Amazing. We’re happy to have you here. Madison, can you tell me a little bit about you? Madison Leatham: Yeah, of course. Happy to. I am based out of Salt Lake City, Utah, and I am an account executive on the public sector team here at Pluralsight. I started out as a BDR on the public sector team, eventually moved into a manager role, where I led the same team that I started on as a BDR, as well as our team in Australia, and then more recently became an account executive supporting our higher education partnerships specifically. RR: I can’t wait to dig into all of this wonderful work and experience that you guys have, and then all the complexity and challenges that kind of come with that. So Lisa, I’d love if you could set the stage for us: who Pluralsight is, what you do, who you serve, all that goodness. LM: Absolutely. And Madison, I’m gonna ask you to keep me honest, ’cause I’d love from a seller’s perspective how you would change my pitch. But we are an online learning and workforce development platform serving businesses and individuals alike with on-demand courses, hands-on labs, and skill assessments that help bridge the skill gaps in areas like AI, cybersecurity, and software development, and so on.  RR: With that context in mind, I think I’d like to jump into what that world of work kind of looks like today. So Madison, from a sales perspective — BDR and AE roles, managerial roles, helping BDRs succeed — you’ve kind of seen it all.  When we look at where we are today versus where things were when you started, what’s changed most about selling over the last few years, and where do you see sellers still struggling the most? ML: So just to talk about both sides of it, starting with prospecting, there’s definitely more of an expectation of personalization and effort. The spray and pray tactics just don’t work. People are a lot more risk-averse. They’re just more busy.  You have to do something different to really cut through the noise, prove that you’ve done your homework, and that you deserve their time just based on the research that you’ve done. So finding ways to do something different is always a challenge. It takes more time. I think personally prospecting and getting your foot in the door is really the hardest it’s ever been.  And on the selling side, this might not be really new news, but they say it takes a lot more people to decide on purchasing a product nowadays. You’ll see different studies saying different things, but they all just show how the buying group has jumped up in numbers, so there’s a lot more need for collaboration on both sides of the fence for communicating the value to different stakeholders that might have different goals. And then I’d say multi-threading, getting in front of decision-makers is just consistently one of the most challenging aspects. Sometimes it’s tricky because you wanna keep the relationship strong with your main point of contact, not overstep, but you wanna make sure that the value is still being communicated and the pain points are still being properly uncovered and discussed. And you kind of lose control of that when you’re just relying on one person. So I really see that across all the AEs I’ve talked to, all the AEs on my team, that need to multi-thread and how tricky it can be to communicate that value across different stakeholders and throughout the buying group. RR: So it sounds like there are a lot of challenges out there, and it’s a fine line to walk when it comes to balancing your initial point of contact and then doing all of the work that makes a deal successful. Thinking specifically about the AE challenges that now you in this new role are facing, in your day-to-day, some of these things that we talked about, what would you say is most difficult for you when you’re working deals and trying to keep things moving forward? ML: Just visibility into what matters to those fringe stakeholders. So when I say fringe stakeholders, the ones that you know have some sway, but you don’t have that direct contact with. Maybe they join one call, and they were off camera. And then just trying to figure out how do their goals align with the solution? How can I make sure it’s not just that game of telephone, that everyone understands the vision of the solution and the implementation of the solution so that we can really start to focus on aligning the logistics and next steps. So I’d say it’s just being able to get clear communication and more visibility and more people involved to really get those discussions, give them a little bit more oomph and value with each person that has some sway in the deal. RR: Yeah, because if you can’t find those fringe stakeholders, you’ll kind of go sideways, and you lose the momentum that you spent all that time building. One thing that’s funny here, Lisa, are you taking notes? LM: I am. This is on the fly, and I’m like: “Oh, this is so interesting to learn.” RR: You’re sitting here taking notes, hearing these challenges, and being like, “Hmm, how do these fit into my programs? How can I support this?” So when you’re hearing challenges like this from the field, how do you start thinking about solving them? LM: So it’s about making sure that the field is empowered with the tools that can really help them do that deep, intelligent research so that they can speak to the needs and the pain points of these accounts.  It can’t just be this very generic as you said at the start of the call spray and pray. It can’t be that anymore, and we know that to be a fact. So it’s ensuring that they have the tools available to them, but also knowing all the different ways that those tools can work with them, not against them, so that it can be simplified.  One of the biggest things I care about is reducing tool swivel, making sure that it’s easy for them to get as much done in one place without feeling exhausted by having to go from Gemini to LinkedIn Sales Navigator to Highspot. So trying to make sure it’s as simplified as possible. RR: Having that conversation of swivel chairing has changed so much over the last year. Now there are so many different AI tools that you can layer in, and somehow it seems like the number of tools has shot up. So making it simple is almost harder than ever and a bigger priority than ever. Today, what are you prioritizing, Lisa, to help sellers break through? What’s new? What are you working on to help them cut through that noise and engage buyers effectively? LM: Definitely AI at every step right now, because as you just mentioned, every tool that we use has some level of AI, and making sure that they understand which one is the best one to use in what workflow, in what step: prospecting, outreach, anything like that. So really working hard. And as you said, it feels like the functionality is changing so much right now that I feel like every half day, my strategy of how we’re going to market with AI for our sellers changes. RR: Yeah, and I love that point of utilizing a tool to its fullest. You invest in these things, you need them to work for you. And one of the things that over the years you’ve spoken extensively about is using Digital Rooms as part of the way of simplifying the buyer journey, making it easier to engage your buyers, and then, to your earlier point, Madison, track what’s interesting to them, track who’s in there. So Lisa, with that being a key part of your strategy, can you walk us through why you leaned into that approach? LM: When I was previously at SAP Concur, Digital Rooms were such a huge part of their strategy that they had an entire team dedicated to that. And so when I was there supporting Highspot, I actually didn’t have an opportunity to touch it. It felt like this really powerful feature that seemed unattainable to me. And then when I came to Pluralsight and I was rolling it out here, I had to very quickly learn Digital Rooms, and I have to admit, I was intimidated because of the way that it was handled at my previous employer. But once I came here, I was like, “Oh, it’s actually super easy.” Digital Rooms are very easy to use. It takes just a few minutes to customize one.  And what I think is really important about Digital Rooms is what Madison was saying earlier, we don’t have a lot of opportunities to break through and stand out right now. You can send a link to something, you can add an attachment to an email, but being able to build out this very personalized space like a Digi

According to research by Salesforce, 86% of business buyers are more likely to buy if companies understand their goals, and nowhere is that statistic truer than in the nonprofit sector. So, how do you ensure that your sellers are ready to show up the right way for every buyer?  Riley Rogers: Hi, and welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully.  Here to discuss this topic are Carly Foerster, principal enablement manager, and Conner Smith, mid-market account executive at GoFundMe. Conner, Carly, thank you so much for joining us. We’re super excited to have you here today.  As we’re kicking off, I’d love if you could just tell us a little bit about yourself, your background, and your role. Carly Foerster: First and foremost, I just want to say thank you so much for having us on here. We are honored as always to work with Highspot and to be featured—how exciting for us.  So, my name is Carly Foerster, as you just shared. I am on our revenue enablement team over here at GoFundMe. I’ve actually been here for almost 10 years now, so about a decade of experience with this team, and one fun fact is that I started on the actual sales frontline side at one point way back in the day, which meant that I was working directly with our nonprofit organizations.  I share that because it’s really helped shape how I think about enablement today. I’ve been in that seat. I’ve been where Conner is. I’ve worked and navigated really complex and unique buying cycles here. And what’s really kept me with this team is our mission. It’s this incredible mission to help people help each other, and I also have this incredible opportunity to partner with purpose-driven individuals, just like Conner. You’ve brought the right person on the call here today. It’s been such a privilege to work with these incredible nonprofits and help drive real impact in this world. And one of my favorite parts is I’m still learning every single day, so I hope that I learn something through this podcast. And with that, the person I’m probably going to learn from is Conner, so I’ll toss it to you. Conner Smith: Yeah, Riley, thanks so much for having us on. I’m Conner. I’m a mid-market account executive here at GoFundMe, and I sell fundraising software for nonprofits called GoFundMe Pro, which is the artist formerly known as Classy. It’s the entire arm of GoFundMe that specializes in helping nonprofits just raise more for their missions. I got into sales about four years ago after being a pastor for four years, actually, so I navigated a pretty significant career shift when I went from leading a nonprofit to selling windows, then while I was selling windows, I learned about tech sales and had to go Google what SaaS was and what an SDR was and what an AE was and all those things. I learned and realized, “Okay, I think this is a pretty good path to success and the lifestyle that I’m looking to build.” So I entered as an SDR back in 2023 and quickly moved into an AE role that I then leveraged just a few months after that to ultimately land a spot here at GoFundMe. And it’s really been a great fit because I know the nonprofit world pretty well, and now I get to meld my nonprofit and sales experience together to really help amplify the impact of nonprofits by giving them the tools they need to, like I said, raise more money for their missions. The cherry on top? I get to work with and learn from pros like Carly. RR: You know, I was going to say that was a great introduction to have to follow, and you smashed it. You guys both—those were incredible introductions. I’m super excited to dig into all of this experience that you just kind of high-level skated across. I think there’s a lot to talk about, and I hope a lot to learn.  One thing that you both touched on and that is very apparent throughout both of your career journeys is this shared love for continuous ongoing learning and self-development.  Can you talk to me about where that mindset comes from for you, and then how it shows up in your work? Conner, I’ll toss it to you to start us off. CS: Yeah. I mean, going back, in my previous role in the nonprofit space, learning was a big part of that. You had to wear a whole lot of different hats, and so learning on the fly was a regular part of the job. I think that’s where it comes from for me. But then coming into sales from a different background, I didn’t really have a playbook either. I had to learn fast. I had to learn through trial and error, through feedback, and through a whole lot of mess-ups and failure. And I think that mindset really shows up now in really practical ways. For me, that looks like things like call recordings and listening to those on a regular basis, looking at engagement data, experimenting with different approaches, and not being afraid to fail. You need to be quick to fail.  I had a manager tell me that early on, and I think that was some of the best advice I got. Just get out there and do it. Don’t be afraid of failure because it’s the quickest way to learn. RR: Yeah, and that’s fantastic advice. And I think you built the learning muscle because you had to, and now it’s stuck, and that’s just how you continually improve over time, so I love to hear that. Carly, what about you? CF: Yeah, absolutely. Love learning. We’re big learning fans over here, and Conner, I was going to say, I love that mindset. I think you and I have talked about this, this sentiment of fail fast, fail hard, learn quick, right? That’s a huge part of what we understand as the learning process here. For me in particular, I’m going to take this on a little bit of a personal journey. So one thing you should know about me is that I have very strong core values personally, one of which is to always be learning. So this is really at the heart and core of who I am as a person.  I’ve always had this real natural curiosity in life. I yearn to do and see and experience everything that I can, and I think it’s that sort of innate drive that makes me want to keep growing, to really have that growth mindset. A couple things I wanted to share from a sales lens first. Back when I was a rep, one of my biggest learnings, since Conner shared a few, was that if I were to look around and see who was the most successful on the team, what I could tell you is that the most successful people were not always the ones that had the answers right away. It was often the people who were asking another question, better understanding what they were trying or being asked to do, and then adapting real quick. When I think about our role in enablement now, where that shows up is really how we build our programs. So we focus on the fact that we’re not creating static systems. We’re not creating one-and-done trainings. We’re trying to create systems that are constantly evolving. We try to. We’re not perfect at it, but that is the end game for us. We’re constantly looking at what’s working, what’s not, how we can iterate. Conner even called out a couple of things. We’re looking at recording data, information from Highspot through reporting and analytics to help inform what that looks like. RR: Learning doesn’t always have to be external. Sometimes it’s asking that question of yourself every single day, “How can I be that little bit better? What can I do a little bit differently to serve my customers, to serve my nonprofit partners that little bit better?” And I think that is such an important mindset shift to just be open to that question. On the topic of growth, Carly, you’ve mentioned a couple times that you started your journey at GoFundMe as a seller.  So, having experienced the nonprofit space from both angles, both the sales and the enablement side, what obstacles do you find that your sellers most often encounter now that you are in this place to help them through it? CF: Great question, Riley, and it’s something we’re thinking about every day, right—how can we overcome barriers and friction in our sales process so that we can better support and serve our customers? I think one of the biggest challenges that I learned very early on as a rep and continue to hone in on as an enablement professional in our specific sector is that we’re a little bit off the beaten path from what it means to be in a traditional sales role. It’s because we’re not just selling a product, we’re actually partnering with organizations that are deeply mission-driven. They are incredibly thoughtful about every single cent, every single dollar that they invest, and that’s rightfully so, because so many of the nonprofits we work with are supporting critical solutions for some of the biggest problems in this world. So they have to think about every single dollar that they invest. And so for us, what this sometimes translates into is longer sales cycles, a higher bar for trust. So we are designing our enablement program around those realities.  We’re helping reps to tell as clear of a story as possible, to help personalize our outreach at scale, and to use tools like Digital Rooms through Highspot to create this really thoughtful, almost through-line experience during that deal cycle. At the end of the day, I would almost position it as transitioning from selling to serving. We are here to support nonprofits through this decision to show how we can partner and then to prove ourselves as a partner when they become customers. RR: You know, I think something that comes through as the through line of all of this, just listening to you both speak about your work and the passion that you have for it, is just how important it is to work for a mission-driven or

According to research by Gartner, 84% of business leaders report their company’s identity must significantly change to achieve strategic objectives. But how do you know when the time is right? And more importantly, how do you ensure that change goes smoothly? Riley Rogers: Welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully. According to research by Gartner, 84% of business leaders report their company’s identity must significantly change to achieve strategic objectives. But how do you know when the time is right? And more than that, how do you ensure that the change goes smoothly? Here to discuss this topic is Shelly Luciano, Vice President of Strategy and Operations at Leah. Thank you so much for joining us today, Shelly. I’d love if you could just kick us off by telling us a little bit about yourself, your background, and your role. Shelly Luciano: I’m Shelly Luciano. I’m Brazilian. I studied industrial engineering in Brazil and France. I started my career working in infrastructure and R&D, so that experience gave me a strong foundation in execution early on. Back in 2014, I moved to the UK to pursue my MBA at London Business School. I used business school to transition from a technical background into strategy on a global scale. After my MBA, I spent three and a half years in strategy consulting. That work helped me learn how companies compete in larger markets. What I realized is that although strategy consulting is intellectually fascinating, I was being more and more drawn to the business. So I transitioned into tech about five years ago. I joined what was then ContractPodAI, which is now Leah. Today, I’m Vice President of Strategy and Operations. My team focuses on aligning strategic priorities, supporting cross-functional execution, and ensuring our go-to-market approach reflects both where the company’s headed and what our customers need. One of the most valuable parts of my role is staying close to our customer base. These conversations give me and the company a lot of valuable insight into how the market is evolving and how organizations are actually adopting AI. I then bring these insights back into the organization, back into Leah, to inform product direction, enable our customer success team, and ensure that our strategy remains grounded in real market needs. Ultimately, my role sits at the intersection of strategy, go-to-market execution, and customer insight. RR: I think you have a fascinating role, to be quite frank, and also a really wonderful story. To go from “I’m trained as an engineer,” to “now I’ve got my MBA, I’m in consulting, and today I work in tech and have for the last five years,” that’s really an incredible journey that I imagine must have given you a real wealth of experience that serves you very well at Leah. SL: It’s funny because if you asked me when I graduated in Brazil what I’d be doing now, I wouldn’t have guessed. The world has changed so much. My world has changed so much. So I feel very lucky and blessed to do the job that I do. I really like it. My company’s fascinating. My role is fascinating. My company gives me room to change as long as I’m adding value and my team is adding value. So I’m really happy. RR: Yeah, and that’s certainly evidenced by the fact that you spent five years in one tech company when the average tenure is just over two, so something really must be going right. I’d love to dig a little bit deeper into this exciting, challenging, and evolving role that’s been keeping you at Leah for the last few years. You’re there to keep an eye on what’s happening in the market so your reps can tell a story and your engineering teams can build a product that the market both wants to hear and to see. More than that, you’re also there to break down silos and operationalize your strategy so it really shows up in everyday workflows. In this work, what kind of things tend to crop up—challenges or obstacles that make it difficult to build the connections that bridge that gap between strategy and execution? SL: For me, there are two major challenges I see in equipping internal teams to drive growth. First, strategy and execution often evolve at different speeds. A leadership team can align relatively quickly on a strategic direction, but translating that direction into how hundreds or thousands of people operate day to day can take much longer. For me, strategy only really lands when it keeps showing up in customer conversations. What you portray needs to align with what your client base and the market are seeing. If the people talking to customers every day don’t understand the problems that your company is solving and why, then your strategy hasn’t really landed. It’s just a deck. It’s lovely to build these ideas, but you’ve got to be able to execute on them. As companies scale, the complexity increases much faster than people expect. You have more industries, more personas, a larger product portfolio, and if you don’t have the right systems and alignment, that complexity can create a lot of confusion internally. And if your team is internally confused, then everyone else is too. RR: So your job is to keep an incredibly close pulse on the market and on technology as they both evolve. And it’s a little bit of an endless task because the market will always shift and technology will always evolve. So you’ve got to be right there with it as the voice of reason for the organization, telling everyone, “Okay, here’s what’s happening, and here’s how we’re going to move with it.” As someone who, by job description, is very comfortable with change and evolution, can you share with us how you’re thinking about how Leah, as an AI-first company, is keeping pace through major technology shifts, and then how other organizations should think about translating these shifts into their own organizational and operational processes? SL: Leah has been an AI-first company for years, way before LLMs. What changed with LLMs is the speed and scope at which we can execute our strategy much faster. We’ve been using machine learning in our platform for a long time, so the foundation was already there. We already had a really strong team. What LLMs did was introduce a step change, and our founder, Sarvarth, is a visionary. He saw straight away how that was going to change the game. All these changes in the past few years did not change our direction, but for the client base, what they can really see is that LLMs have expanded the use cases that we can deliver. And I think that’s what matters to customers—how can we solve more of their problems? With Leah, we’ve moved from traditional automation into what we describe as an agentic operating system. That means our AI is not just supporting workflows. We can do much more than that. We can now reason across data, understand context, and orchestrate actions. That is so exciting, as you can imagine, for someone who works in strategy because it feels limitless. Going beyond static workflows, you now have systems that can adapt dynamically to the problems that we’re solving. And that’s where the speed and pace of innovation really comes in. Once you move into an agentic model, you’re no longer limited to predefined use cases. You can continuously expand how AI is applied across not only our internal organization but also our client base. From a strategy and operations perspective, the challenge is not adopting the technology, because we’ve been able to do it and we continue to do it. The challenge is how do we operationalize it? Strategists love frameworks, so if I had to group it, I’d say there are three ways I think about this. The first part is strategic focus. The risk with AI, within all this opportunity, is diffusion. So we need to be deliberate about which use cases we prioritize. We need to define where we can deliver the most value, because being AI-first doesn’t mean doing everything. It means scaling the right use cases. The second part is how do we translate that into go-to-market execution? As I mentioned before, strategy only really lands when your customers can speak about you. Organizations need to understand how to position AI. We need to be able to explain it clearly so we can apply it across different industries and contexts. That’s where systems like Highspot can really help us translate this within our organization and externally. The third thing is continuous customer feedback loops, because customer proximity is the most valuable strategic signal we can have. To be a strategist in tech, your goal is not to define a static AI strategy. You’re always on a feedback loop, and you need to be agile. The tools and teams that support you need to be comfortable with always learning and always putting our best foot forward. RR: So as you alluded to, you and the team actually recently went through a rebrand. From ContractPodAI, you became Leah, named after the organization’s flagship AI offering. I’d be curious to hear how, with these challenges to strategy-aligned execution in mind, you and the team made sure that everyone was telling the same story and supporting the same strategy, even as the brand message and narrative shifted so drastically. SL: Leah was already a product of ours that had taken a bigger and bigger piece of our client base. So moving from ContractPodAI, which was very contract-focused, into Leah made sense because the Leah product had become a much bigger part of who we were and our identity. When we came into becoming the Leah brand, we were ready in many ways. You’re never fully ready for a full rebrand. There’s still a lot of work. But we had t

According to Highspot’s Go-To-Market Gap Report, 98% of leaders say their GTM strategy is active, but only 10% see it driving results. The reason for that? Strategy abounds. Real meaningful execution, not so much. So how do you overcome the go-to-market performance gap and bridge that growing rift between strategy and execution? Riley Rogers: Hi, and welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully. Here to discuss this topic is Jacob Keith, senior revenue enablement specialist at HealthJoy. Thank you so much for joining us today, Jacob. I’m super excited to dive into your experience. So could you kick us off just by sharing a little bit about yourself, your background, and the role you’re in currently? Jacob Keeth: Yeah, absolutely. Also, Riley, thanks so much for having me on. I’m really grateful and excited that we get the chance to chat about something so consequential and oddly kind of fun. So I’m just looking forward to it. My name’s Jacob. Professionally speaking, I’ve been working in enablement for just shy of five years and worked in sales for a year prior to that doing SDR prospecting work. I’ve done all types of enablement, everything from onboarding-focused work to focusing on BDRs and prospecting. Now at my current company, HealthJoy, it’s been so much fun. We’re operating in primarily a channel sales method, so we’re working through individuals who then sell our product, which has been a really fun and complicated task from the enablement perspective. We’ll dive all into that today. RR: Awesome. So exciting that you’re in a role that’s challenging you and building on all of those skills that you were learning and picking up along the way. Before we jump in, I’d love if you could set the stage for those of us not familiar with HealthJoy—who you are, what you do, who you serve, and then maybe a little bit of that sales motion that you touched on. JK: HealthJoy is a benefits operating system, and really what we do is help make sure that companies’ benefits strategies and plans actually work as designed. What do I mean by that?  Well, I’m sure, Riley, as you’ve experienced too, companies typically have a pretty fragmented benefits plan, right? There’s the medical plan, the dental plan, maybe individual solutions. Usually these companies all have different logins, different ways to access them, and there’s not necessarily a concrete place where you can go to get all that information inside of one environment. Also, the reality is, if I’m debating whether I need to go to the ER right now, I can tell you the last place I’m gonna go is logging into my company’s intranet to figure out which ER is best applicable to me and which one is likely gonna work with my insurance. We make healthcare decisions through the path of least resistance, and frankly, they’re usually made in situations where we don’t have the luxury of time. This is really where HealthJoy can come in.  With HealthJoy, companies can unite that benefits ecosystem into one seamless platform. We use an AI assistant called Joy AI, as well as human concierges, to give our end members or employees personalized guidance and proactive support. That’s really where HealthJoy finds itself: being that benefits operating system that puts everything together and helps you, Riley, make the right decision at the right time. So that’s the big-picture view of what the company is and what we do.  Now, how do we actually do it? The way HealthJoy operates is we work through what you’d call a benefits consultant. Your HR team at your business is probably working with an external benefits agency, consultant, or broker to help curate and strategize that benefits plan to maximize its effectiveness and cost for the business. We work through them, build really meaningful relationships with brokers all across the United States, and then from there, when there’s strategic alignment and the broker believes in us and our message, they’ll introduce us to clients where they think we can help that company advance its mission because they align with the kinds of things we’re offering. So that’s what we’d call a channel sales methodology. We’re working with people who then sell in tandem with us. From an enablement perspective, you’re not only trying to enable your selling team, but you’re also asking: how can I best train these folks to then go and enable the hundreds of brokers they’re all working with individually around the country? RR: I think your marketing and comms team is really gonna be thrilled because that was a great pitch. It almost seems like you have to, as an enabler, play a game of telephone. You have one message to share with folks internally that you then need them to get out the right way externally. It sounds like it’s quite the challenge, especially given that, like you shared, HealthJoy is in kind of a unique position at the intersection of tech and all of the wonderful complexity that comes with healthcare. So how does that industry challenge shape the way your go-to-market teams need to operate, and what kind of challenges does that create for you on the enablement side? JK: Yeah, that complexity gives me a lot of job security. So it is a real challenge. One thing HealthJoy has gotten really good at over the last year is defining who our ideal customer is. Is it the end-user employer? Is it the member who would experience it? Is it the broker we’re targeting? And it really is the broker. Those are the folks we’re working with, building meaningful relationships with, and who can open up so much opportunity for us as a business. When a broker believes in us, it pays huge dividends in both effectiveness and outcomes. At that intersection of tech and healthcare, another interesting element that often shows up in enablement is onboarding. You look at who we hire as our sales reps—we’re looking for people who typically have a strong background in healthcare and great existing relationships with brokers around the United States. Then they’re coming into an environment where maybe they weren’t in a tech environment at all. So how do we equip these individuals to feel really confident in a remote sales environment that’s very tech-forward? HealthJoy as a company is also heavily leaning into AI internally and externally. So convincing our sellers that the direction we’re taking as a company is one they can understand, intuit, and promote into the market is a real challenge. It’s multi-step. An adage I try to live by as an enabler—and this is really a hallmark of adult education—is the question: what’s in it for me? If it’s not relevant for that seller, they’re not going to retain it, even if they want to. Even if their boss is pleading with them, “You have to know this. This has to make sense for you.” If there’s not an immediate connection to why this matters for me and my paycheck at the end of the day, it’s not going to stick. That’s not selfishness. That’s just the reality of how adults learn and prioritize what’s important. So for us, we have to make sure the messages we’re positioning—whether they’re for the seller to use, for the seller to communicate to their broker, or for the end member—have a really clear through line. The rep needs to know what’s in it for them and who that message is for throughout. It can be complicated. It can be a real challenge to make sure we’re nailing that every single time. I get a negative shiver down my spine every time I hear a message about what HealthJoy is that doesn’t align with the message we’re putting out into the market. Because I know for every one rep who says that, there’s probably a dozen brokers who hear it too. And we’re working with brokers over the course of years. So if that broker got a demo of HealthJoy three years ago and thinks, “I know it. I’m good to move forward,” how do we keep our existing brokers who love us educated on what’s happening across the market and how we’re evolving as a company? RR: It’s kind of fascinating. I feel like sometimes you talk to folks and the challenge of bringing in sellers is getting them up to speed on the complex side of the industry. If I’m chatting with fintech customers, it’s understanding the financial environment. Or with health tech customers, it’s learning how to speak about healthcare. But you have the reverse challenge. You’re bringing in sales reps who maybe were in the field or in more traditional spaces, and now you need to get them up to speed on all of the innovation that comes with a tech company. So it’s a very unique challenge, and it sounds like it’s one you’re well-equipped to tackle. You described yourself as someone who really excels at turning ideas into repeatable, measurable processes. I’d love if you could tell us, from your perspective, how you’re connecting strategy to execution, because as that stat we opened with tells us, things tend to get lost in translation. JK: For me, when it comes to turning things into repeatable and measurable processes—especially as an enablement team of one—my thought is this: pick really carefully and be ready to pivot. Especially in a startup environment, odds are if you’re an enablement team of one, you’re in a company that’s still developing.  There isn’t a strong adherence to “the way things have always been,” or a large team and lots of infrastructure supporting the organization. It’s you. You are the brand of enablement. Who you represent and how you show up is what enablement is perceived as by your organization every single time. So with that, be re

According to research from Promotional Products Association International, the promotional products industry is digitizing, and it is digitizing fast. Last year, online sales represented 25% of total industry sales, which is a 19% increase year over year. As the industry shifts, promotional product organizations like Polyconcept North America are as well. So, how do you manage the change? Riley Rogers: Hi, and welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully.  Here to discuss this topic are Nicole Zuniga, sales enablement manager, and Lanya Trypupenko, marketing lead acquisition specialist at PCNA. Thank you so much for joining us today. We’re really excited to have you here and to dig into all the wonderful work you’re doing at PCNA. Before we kick off, I’d love to learn a little bit about you both, your background, and your role.  Nicole, would you like to start us off? Nicole Zuniga: Sure. So I am sales enablement manager. I run our Highspot platform. I do have sales background experience, and I often go out to customer events and dive back into my sales role when we’re doing those.  But mainly when it comes to Highspot, I’m trying to create a lot of or limit a lot of that gray area between sales and marketing and make it really easy for not only our sales reps to be able to provide guidance and value to our customers, but then our customers take a lot of that same content and reuse it for working with their customers. RR: Wonderful. Well, we’re happy to have you here. Lanya, would you mind telling us a little bit about yourself? Lanya Trypupenko: I am currently the marketing lead acquisition specialist, also known as the new account specialist. So I onboard the majority of our new accounts and just make sure they have all the information and everything they need to kinda get started and be successful with PCNA. And then my background, I’ve worked in marketing and account management for ten plus years, always with different types of products, such as jewelry, eyewear, telecommunications, and now promotional products. RR: Fantastic. Well, I am really looking forward to digging into all of that experience and how it shows up for you at PCNA. Before we get into the nitty-gritty details, Nicole, would you mind giving us a high-level overview of PCNA’s business, what you sell, who you sell it to, especially knowing that you guys have a little bit of a unique sales structure?  I’d love if you could walk us through it and kind of set that foundation for our listeners. NZ: Absolutely. So anybody who has received a piece of swag or some sort of giveaway, that is what we do. So we are a promotional product supplier. We import, design, and decorate promotional items, a 50 cent pen all the way up to a $300, um, leather tote bag or leather, uh, duffel bag. So we have quite an array of products that we offer. And we work with a distributor network, so it’s a very unique way that we do business. Instead of us working directly with the public, our distributors will then market to, could be marketing firms, it could be directly very large corporations, it could be small businesses. And so we are promoting to the promoter of our products. RR: I think folks listening in will probably be a little bit astonished by the scale that you’re dealing with. There are, you know, potentially thousands of products. They change seasonally. They just change depending upon the type of buyer that you’re targeting, the budget that you have, all sorts of factors. When you’re working at a scale like this and you’re working to enable at a scale like this, what starts to break down? What cracks do you see as you’re helping your teams take all of these products to market? NZ: You’re looking at, especially when you look at seasonality or even upcoming national days, their buying events coming, and that kind of takes out, like, that first layer of, “I don’t know where to start.” The hardest question or the hardest thing to get is, um, “Give me, like, five or 10 ideas for this price range,” but not knowing what is the use case, what is the theme, who is the audience. So, that’s what a lot of our resources are for, to whittle out some of those questions to then get down to the nitty-gritty of what is going to hit with the customer. Let’s talk about breast cancer awareness. It’s not necessarily going to be a one-for-one. It depends on what our distributors are working on with their customers. It could be maybe they just want a simple sport pack to be able to give out to their customers. It could be a plastic cup. It could also be a really nice piece of apparel. So we’re trying to provide a lot of those ideas. Typically, we have flyers of product ideas for those buying moments, and that’s mainly what’s housed in Highspot, to make it easier to just have a collection of ideas to inspire more of those discussions with our distributors and then also distributors with their customers. The Sales Plays have been very, very important to us. It’s like a single source of truth now, that with our training, it helps keep everybody on the same page. It’s like how we position it, where we win, competitive insights, how to talk about it. When I was on the sales team, it was like, “What did they say? Who said that?” And it was a game of telephone.  So, now we have a one-stop shop, one resource that has all of the things all weaved together—the what to know, what to do, what to say, what to show. When I developed our quarterly sales playbook, put it in the same exact format, so that way everybody’s used to that exact same format of all the resources that we provide, which is kind of like a big Sales Play for everyone for the quarter for messaging. RR: So it seems like the challenge is really less about navigating through an endless array of options, and more so about creating an efficient system for packaging and sharing out relevant materials that sellers can find and run with, depending upon the type of customer that they’re speaking with.  So with that little bit of frame of reference for the business about how PCNA operates, as well as what’s difficult about how it operates, Lanya, I’d love to hear from you about how some of these challenges show up in your work. LT: Yeah. I would say my initial challenges are really in making sure that, like, the customer has the information that they need from the beginning, that they understand PCNA, and then getting to the place where they’re kind of comfortable placing the order, that they can kind of self-service, you know, go look for product themselves. Of course, as the accounts do grow, it’s also important for me to be able to assist them based on their specific business and industry needs.  So, that’s kind of where the tools, like the Highspot tools that Nicole puts together, are super helpful because then I can go in and just grab something that’s maybe specific to, like, someone that has a healthcare client versus someone that has a corporate client. RR: So we’ve heard a few challenges here, I think ones that make a lot of sense for the environment you’re working in. One thing I’m curious about is that while some of these challenges sound familiar, one thing that might not be familiar to a lot of folks is that you work in a pretty unique environment. It’s still very hands-on.  Nicole, as you mentioned, you’re often at trade shows. You’re supporting events. You’re boots on the ground with the sales teams handling in-person selling right alongside them.  So, what led you to decide that it was time to take a more digital approach, and why did Highspot come into the picture? NZ: Going back to that gray area, we had resources. It was not easy to find. Our website is focused on finding and searching products, and even our own internal people have a hard time finding content on the website.  And the thing we really loved about Highspot is it reduces that searching time. People are able to find things really quickly. We can put them into certain spots within Highspot. We can tag them. And the filters—I always say to anybody that I work on with hands-on training—filters are your friend, and it makes it really easy to quickly find the things that you’re looking for. And then when we send out things, like it could be our new summer lookbook, there are so many products in there, but the insights that someone gets of like, “They told me they were really interested in bags, but they spent five minutes over here on this golf,” that is a great way of a little lead generation to then set up and further those conversations and figure out that maybe that’s really what they were looking for. Of course, using the, “Did you get my email first?” because you don’t wanna necessarily, oh, sound the alarms that you were looking at every single thing they were looking at. But that really helps us narrow down those options to then provide more value and get quickly to what the customer wants. RR: I can definitely see that making a lot of sense as you look across a changing industry and realize, maybe there are some things that we could do differently, especially, you know, as you said, having been through the ringer as a seller yourself. I also love that use case of engagement insights shaping your next steps, because to your point, you know, sometimes your customers come in with an idea of what they want, and then you share all sorts of wonderful, shiny options with them, and they go, “Well, hold on a minute. There’s a lot more I could get there.” So that’s really clever, and I like that a lot.  Lanya, I know that this kind of shows up a lot in your work. I

According to research by G2, organizations with a sales enablement strategy achieve, on average, a 49% higher win rate on forecasted deals. But to see these kinds of returns, you first need to get sellers, leaders, and the business itself bought into the value of enablement. So, how do you build confidence in the function’s value across stakeholders at every level of the business?  Riley Rogers: Hi, and welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace and how to navigate them successfully. Here to discuss this topic are Mateo Perretta, senior director of revenue enablement, and Bety Garcia, sales enablement program manager at Loopio. Thank you both so much for joining us. I’m really excited to have you here and to learn a little bit from your expertise. Before we kick off, would you mind telling us a little bit about yourself, your background, and your role? Betty, maybe can we start with you? Bety Garcia: Yeah, no, thank you for having us. I’m a sales enablement program manager here at Loopio. I’ve been in enablement for a little bit under a decade at this point.  I’ve always been part of pretty small teams, so I’ve had to be pretty creative when it comes to, you know, how do we get a whole bunch of different initiatives done across the board. RR: The story of scrappy teams and figuring it out is one that a lot of folks in enablement know well, so I’m sure there will be a lot of similarities in what you have to share.  Matteo, would you mind telling us a little bit about your journey? Matteo Perretta: Yeah, absolutely. And thanks for having us today. You know, it’s interesting. I tell a story about, I  started my career in telemarketing. I was in sales support did sales myself. I became a sales leader. And then I stumbled into this thing called sales effectiveness, sales excellence, sales enablement. It’s changed over the years, but probably in 2010 when I stumbled across it. And what I’d like to say is I’ve moved from the game of quantity to quality. RR: From your perspective, having now stumbled into sales effectiveness, now sales enablement and led it at several different companies, how would you define what great enablement looks like, especially for growing GTM organizations like Loopio? MP: I’ve walked into sales organizations and the first feedback I get is, we’ve done way too much enablement. We really haven’t had any time to digest it. And that’s usually a symptom of teams being reactive.  What I mean by that is sales leaders and salespeople will come to you and tell you they need all this enablement and you just keep filling that funnel and you almost become a catch-all for everyone versus being proactive and really looking at, you know, data and insights to kind of figure out what do we need to do and how does that actually align to the KPIs or the results and what the organization’s ultimately trying to do?  And so for me, it’s really understanding: “What do we have, what are our assets, and how do we align them to our goals?” When you do that, you become a partner and you show them with insight what’s important versus just, you know, being this order taker and doing a lot of enablement that just isn’t resonating. RR: The other piece of the puzzle is giving enablement the agency to kind of direct course and build a strategy with sellers in mind, but also not built for every single thing that every single seller needs, because that is an endless hamster wheel that you will never escape. So I love that call out and I’m curious to hear how technology fits into that when it comes to building a great enablement strategy. Betty, you’ve been with Loopio through a couple of enablement tool changes, including when Loopio made the decision to step away from a previous tool and kind of run without one for six months. Can you walk us through what wasn’t working then and why for a little while maybe no tool was better than the wrong tool? BG: It wasn’t so much that we had issues with the tool itself, but more so what it had become at the time. Right? So like we have a ton of unorganized, outdated content in there. And the problem with something like this at the time is that users don’t tend to be loud about those issues. They tend to just find workarounds.  On one hand, you might have, you know, top performers starting to create all of their own content that maybe they share with a few individuals and those individuals might share with others. On the other, you have the opposite of that, where you have a whole bunch of outdated content out there that’s just circulating.  And so what this creates is a few different challenges for the team that doesn’t necessarily go noticed right away, which is that the messaging becomes completely random depending on, you know, who knows what, their experience level. That then translates to performance. So, now it’s not just an issue of, you know, do we have a good source of content for everybody to draw from? It’s, you know, how do we get everybody back to performing at the same level with the same level of knowledge and the same level of information?  So that was sort of like, you know, stepping back. That was the real challenge that we were looking to solve. And part of what, having that time in between not having a tool and then looking for a new solution to bring into Loopio was having the time to plan for that, right? If we’re gonna do this, how are we gonna do it? There was a lot of planning involved in that and really trying to make that decision and, and started to tie it to the real business challenges that we had there, which was how do we get everybody working at the same level once again? RR: Yeah. And I’m really excited to dig into how you rebuilt that trust, because that’s not easy. So, we’ll touch on that in a minute. I want to start with the decision over that six-month period to strategize how we’re gonna rebuild and then who we’re gonna rebuild with, and eventually that decision led you here to Highspot.  Bety, you mentioned that you’d launched Highspot at a previous company. What made you confident over this time as your planning, planning, planning, that this would be the right tool and you’d be able to build that trust in that confidence with your users with it? BG: I think it, I mean, I had a huge advantage, right? Because I had done it a few times, and I mean, had a great positive experience working with the team at Highspot, but also I knew that it was a really great tool, right? It sort of sells itself when it’s launched correctly, right? So instead of evaluating the tool itself, from that standpoint, it was like, great.How do we get strategic about doing a launch that’s gonna be really impactful.  And that looked like doing cross-functional partnerships. So working with marketing and product, it wasn’t just an enablement initiative anymore. We really did spend a lot of time doing a ton of content review across the board and reevaluating what it was that we wanted to arm the team with. And then in fact, actually starting to anchor some of our own enablement initiatives into the launch of the tool itself.  So when we did launch Highspot at, we actually also relaunched our onboarding program and we launched a whole new product to enablement program. Now, we were touching on the needs of marketing, the needs of product, the needs of our sales organization when it came to even just onboarding and starting to ramp up ours. And we could really start to show that impact very quickly across many different areas. RR: So from that moment, you’ve reached a pretty stable place with the platform and have built out a really robust environment that, just looking at the data, is well utilized by your teams. Matteo, from a leadership perspective, as someone who came in a little bit post-launch: When you joined Loopio and started looking at what you wanted the strategy to look like and the enablement approach to look like, how did Highspot start fitting into your vision as you were thinking about high priority initiatives, things like onboarding, things like, you know, Loopio’s, monthly product launch cadence? MP: Yeah. I mean, I think it’s interesting when people say enablement or to define enablement, it’s what’s the modality? And I think a lot of times. People see enablement with a classroom and an instructor up all the time. And one of the things, you know, I kept saying was, you know, it can’t be Bety and me in a classroom every time doing this. And so really Highspot allows us to give them different modalities and look at ways of giving people what they need when they need it. And so I think that was part of the strategy. The other thing was, you know, I’ve spent some time with a Highspot team, like, how are we gonna measure this? How are we gonna prove ROI to our leaders so that we can get them to buy in? I know in speaking to other sales enablement leaders, one of the biggest challenges is actually getting people to complete the courses, and so we’ve gotta make it easy for them. So with Highspot, we can quickly pull reports, help people understand who’s completing, who’s not, but then take it one level deeper.  Some of the work that Bety’s done, we’re actually able to look at who are our top performers and how much time they are spending in Highspot versus those that aren’t top performers. There’s a correlation there. To me, that’s the most valuable thing, being able to go back to our leaders and saying: “This is working, this isn’t working. Here’s why we need to change and, and here’s the insight behind it.” RR: You mentioned something interesting there, which is the ability to, at a very granular individual level, s