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Manny Medina, Co-Founder and CEO of Paid, the monetization platform for AI agents, and the founder who took Outreach from nothing, joins Sam Jacobs, AJ Bruno, and Asad Zaman in person on how to price AI agents once seats stop making sense. Topics include why every SaaS company needs its own agents before someone else's run on its MCP layer, why a token is the wrong unit of value, and the itemized phone bill every agent builder owes its buyers. Plus, why fixed-price deals win logos but stall expansion, the case for 40% to 60% gross margins in the agent era, and what Satya Nadella told Manny in a green room. Key Takeaways: - Price the work your agent does, not the seats it fills. In SaaS you sell 100 seats, procurement sees 20 in heavy use, and the renewal shrinks to 50. With agents, "if you've sold 100 seats and only 2 were hyper-users, you don't care because you're charging for all the uses and all the value those 2 seats were getting." For now that pricing lives between effort and output, because true outcome pricing needs attribution, and as Manny put it, "Attribution is really hard." - Make the bill readable before you argue about ROI. Manny compares it to the old itemized phone bill, where you went straight to the biggest line and asked, "Did I really call Pakistan from New York?" Tokens can't play that role: "A token should not be a unit of value for charging because a token is really kind of like the inside secret." Show the buyer the research, deck, or analysis the agent produced, because "explainability is like the first rung in the ladder." - Fixed pricing is easy money that boxes you in at renewal. Enterprises are buying one of each right now, so "new logo is not hard. Expansion is hard." Teams that land logos on fixed price hit the first renewal with nowhere to go, which is why Paid opens with a monetization consultant and takes a percentage of revenue: "You grow, I grow." - Plan for thinner margins and narrower markets. Manny learned Amazon's margins cold (books 20%, electronics 7%, jewelry 3%) and calls SaaS's 70 to 80% an anomaly of cheap money: "I feel like a normal, you know, software business will be running on 40% margins, 60% tops." Connect with the Hosts & Guests:   Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: Manny Medina, Co-Founder & CEO at Paid - https://www.linkedin.com/in/medinism/   Topline is more than a podcast:   Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Check us out on YouTube for the #1 video podcast for founders, operators, and investors in B2B tech: https://www.youtube.com/@TOPLINE-Media Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack   Chapters: 00:00 Introducing Manny Medina 01:37 What Paid Is Building 04:38 Will All Software Go Agentic? 06:35 The 100-Seat Renewal Problem 10:02 An Itemized Phone Bill for Agents 13:33 Why Outcome Pricing Takes Time 19:04 Open Source vs. Frontier Models 26:41 Pricing Agents Is an NRR Problem 33:11 Why Manny Won't Build Workflows 35:39 Fundraising Lessons From Outreach 41:10 Life Is Path Dependent 45:46 Culture Is the Exhaust of Winning 47:50 Is AI Spend Still Experimental? 58:22 The End of 80% Software Margins

You have the CRM. You have the data. You have the sales team. You have the AI tools. So why does everything still feel broken? Ramin Heydari, CEO & President of XYZies, has spent more than 30 years building businesses across telecom, sales, distribution, and technology. In this episode of Topline Spotlight, he explains why fragmented systems can become one of the biggest obstacles to growth and why AI requires businesses to rethink how they operate, not simply add another tool. Sam Jacobs sits down with Ramin to unpack the shift from traditional growth to 10X thinking, the problem with scattered data and sales systems, and how AI can create real-time visibility and coaching across an organization. What we get into: - Why businesses need to think beyond traditional growth - Why adding AI to existing software isn't enough - The hidden cost of fragmented systems and data - How AI can provide real-time coaching and performance feedback - Why continuous improvement matters more than occasional reviews - What a truly AI-powered CRM could look like - The leadership principle: "The future belongs to those who can see it before it becomes obvious." Chapters: 02:01 Why XYZ Exists And Why "The Details" Matter 03:27 Building the Smarter Home With AI 04:10 Information Overload and Better Decisions 07:32 Why Businesses Need to Think 10X 09:47 The Problem With Too Many Systems 10:15 The Human Side of the Technology Problem 10:58 The "Dream CRM" 12:49 Real-Time AI Coaching and Continuous Improvement 15:07 The Hidden Cost of Enterprise Software 17:56 Ramin's Leadership Lessons 19:20 Where to Find XYZies 19:46 Outro Try XYZies: xyzies.com

Harvey's gross margin fell from roughly positive 50% at the start of 2026 to negative 50% by June, so every $1 of revenue cost $1.50 to deliver. Sam Jacobs, CEO of Pavilion, AJ Bruno, CEO of QuotaPath, and Asad Zaman, CEO of STA, go hosts-only on when AI growth justifies margins like that, why open weight models are no substitute for frontier intelligence, and what happens to the application layer if the exuberant market funding it goes away. Plus, AJ's 100x raise from 2021, a 68% jump in tech M&A and what it means for employee equity, and a Bulls and Bears round on AI catastrophe before 2031. Key Takeaways: - Negative gross margins can be a phase if there's a way out. Sam's straw man: "Above 200% growth, I can tolerate bad margins temporarily if you can show me you have a path to a good business." Between 100% and 200% he wants "a clear improving trajectory," and below 50% the margins have to be good. - Cheaper models fix the margin line but can break the product. Asad likened the switch to open weight models to "going from hiring people only from Harvard to then going and hiring people from the worst university you can find or some mid-tier university and saying it's the same thing." That leaves application companies "completely at the behest of these model companies." - The 2021 hangover is still on cap tables. AJ raised QuotaPath's Series B "at a 100x valuation in '21," but with SaaS multiples at "1x or less than 1x," he said, "If I wanted to go sell QuotaPath today, I really couldn't find a buyer." Asad countered that secondaries changed the math: "The founders are making a lot of money along the way." Connect with the Hosts: Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Topline is more than a podcast: Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Check us out on YouTube for the #1 video podcast for founders, operators, and investors in B2B tech: https://www.youtube.com/@TOPLINE-Media Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack Chapters:  00:00 The Math Of AI, Deals, And Equity 02:03 SaaS Margins Were A Law Of Nature 03:24 Harvey's Margins Went To Negative 50% 04:18 Sam's 200% Growth Straw Man 05:46 Open Weight Models Aren't Harvard 14:13 Open Models Vs. Frontier Lab Economics 19:01 What Would You Spend $1M On? 30:08 Bullish Or Bearish On The AI Trade? 34:15 Walrath's Warning And A 100x Round 36:37 Secondaries Changed The Founder Math 42:35 Most Companies Never Get The Choice 47:32 Corporate M&A Is Surging 52:04 Should Equity Vest Monthly? 57:40 AJ's Case For Performance Equity 1:02:49 Bulls And Bears: AI Catastrophe

Keith Peiris, Co-Founder and CEO of Lightfield, joins Sam Jacobs, AJ Bruno, and Asad Zaman to talk about building an agentic CRM that launched in November 2025, has been adopted by more than 5,000 customers, and just raised a $47 million Series A led by Andreessen Horowitz. Topics include why every system of record was really a forecasting tool, how to get reliable output from non-deterministic models, and the two reasons companies actually rip out Salesforce or HubSpot. Plus, a spirited debate on whether the SaaS partner ecosystem is dead, why AI-native deal sizes at 200-person companies can rival enterprise contracts, and how Lightfield landed on a mix of seat-based and consumption pricing.   Key Takeaways:   - Plan for models that will always make some mistakes. Keith builds Lightfield on the assumption that models stay non-deterministic, and calls reliability "a harness problem" that they're making fantastic progress against. - Use LLMs for insight and plain code for arithmetic. When Asad asked whether auditing AI forecasts saves anyone any time, Keith described a one-time implementation where Lightfield's head of finance checked every formula: "We converted some things from prompts to real code, right? I don't want LLMs doing math. I want real code doing math." That got the dashboards 95% of the way there, leaving the models to flag which deals were on the cusp because of missing features or competition. - Slightly better AI output won't justify replacing a CRM. After several rip-and-replace projects off Salesforce and HubSpot, Keith said marginally better agentic emails are "not a good enough reason to change a system of record." The two reasons that do move customers are believing one model of the business improves every stage of the revenue funnel, with SDRs pulling real-time case studies from customer success, and higher-level scenario planning, where "the modeling really matters. The data completion really matters." - Put predictable work in the seat price and meter the work with visible ROI. Lightfield tried both extremes, and pure consumption backfired: "It's like going to a store where everything's really expensive, that our customers didn't touch anything." The seat and platform fee now covers the core CRM, call recording, and the data model, while pipeline generation, AI workflow automations, and scenario planning run on consumption, because "most revenue leaders, CEOs… have an uncapped budget for business intelligence."   Connect with the Hosts & Guests:   Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: Keith Peiris, Co-Founder & CEO at Lightfield - https://www.linkedin.com/in/keithpeiris/   Topline is more than a Podcast:   Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Check us out on YouTube for the #1 video podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack

What happens when a seasoned GTM leader becomes CEO for the first time and steps into a founder-led company with a global team?  In this episode, Eric Anderson, CEO of Walnut, shares what it's really like to take over a business built by someone else. He talks with AJ Bruno about building trust across time zones, rebuilding the go-to-market motion, and making bold decisions while honoring legacy culture.  From listening tours to tough calls on pricing and segmentation, Eric opens up about the challenges and wins of his first six months in the role. Eric talks about: - What it's really like to step into a founder-led company as a first-time CEO - Building trust and alignment across a global, distributed leadership team - Why CEOs need to be willing to make bold and unpopular decisions - The challenge of walking away from revenue that doesn't fit the business - How pricing and market segmentation can force difficult but necessary changes - Why rebuilding the GTM organization can unlock a company's next stage of growth Chapters 00:00 Introduction to Eric Anderson and Walnut 02:30 From GTM Leader to First-Time CEO 06:49 Leading Across Cultures and Time Zones 09:11 The Boardroom: A New CEO's Balancing Act 11:36 Why CEOs Have to Make the Hard Calls 15:00 The Cost of Trying to Serve Everyone 16:52 Rebuilding Walnut for What's Next 18:30 Where to Find Eric and Walnut Try Walnut: walnut.io

Jen Igartua, CEO at Go Nimbly, joins Sam Jacobs, AJ Bruno, and Asad Zaman. Her client roster is wild: Fireworks AI, Perplexity, Exa, and Wispr Flow, plus some of the biggest names in SaaS. Topics in today's episode include how the fastest-growing AI-native companies are growing in spite of their revenue operations (not because of them), the first project she runs when she wants to show ROI fast, and how she makes the case that RevOps is a support function and always was. Plus, whether the GTM engineer is anything more than RevOps with better marketing (and more)! Key Takeaways: - Operational debt at the fastest-growing AI companies tracks demand, not management quality. Go Nimbly's second customer was Zendesk in 2016, where the head of IT told her "oh, we've grown in spite of our operations." Jen shares what it takes to make a difference at the breakneck pace these environments demand. - RevOps spent a decade insisting it was strategic, and Jen thinks that cost the function credibility with the sellers it exists to serve. As she says in the episode: "I think that operators have been doing an injustice to sellers for a long time. And we are starting to really take onus of the fact that revenue operations needs to be a support function to the sales team. And we've been fighting it forever. We are not a support function. And I'm like, we actually are." Asad, who has argued the same line for years, put the failure mode in football terms: "if a goalkeeper starts trying to play like a striker, you don't let in a lot of goals, right?" - In a people business, staffing is the product, and Jen only learned that after COVID took Go Nimbly down to 20 people. The rule she rebuilt around is "I should only take projects of skills that I want to nurture," then staff someone who is 80% of the way there so the last 20% is stretch. "Our whole job is playing Tetris with resources." She is equally direct about what did not work: "I poured a bunch of money in being tech enabled... I burned millions of dollars trying to do it," because at her clients' scale "everything's custom." The payoff line is the one to keep: "if you nail staffing, you grow a really great services organization." Connect with the Hosts & Guests: Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: Jen Igartua, CEO at Go Nimbly - https://www.linkedin.com/in/jen-igartua/ Topline is more than a podcast: Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack 00:00 Introducing Jen Igartua 02:15 Growing In Spite Of Their Operations 05:46 Top Of Funnel Is The First Fix 06:39 What AI-Native Ops Teams Actually Have 10:50 The Twenty-Rep Qualification Bar 11:37 Is Sales More Broken Than Before 15:00 RevOps Is A Support Function 16:29 Do Great Products Make Great Sellers 22:51 Caesars, COVID, And Twenty People 24:56 Lessons From A Services Business 28:21 Staffing Is The Whole Game 31:10 Why Contractors Do Not Work 40:09 What Is A GTM Engineer Really 49:26 What Scares Jen About 2027 54:40 Bulls and Bears

Matt Allison, CEO and Founder of Handraise, joins us to share why he's skipping the SMB trap and building an AI-powered media intelligence platform for enterprise from day one. Drawing on hard-won lessons from scaling TrendKite, Matt breaks down how Handraise is targeting $30K+ deals with brands like Walgreens and Hershey, the importance of patience in early go-to-market, and how AI is helping them build a more thoughtful, scalable, and enterprise-ready product from the start. Matt also talks about: - Why Handraise is skipping the SMB trap and going enterprise from day one - What TrendKite taught him about building for high-value, high-retention customers - Why patience and discipline matter when you're building an enterprise GTM motion - How AI is helping Handraise build a more sophisticated product with a lean team - Why being AI-first changes what's possible in product development - How to build a sustainable business without chasing hypergrowth at all costs Chapters: 00:00 Introduction to Matt Allison and Handraise 01:15 Why Handraise Is Going Enterprise From Day One 08:46 The Challenge: Building for $30K+ Enterprise Deals 11:56 Why Patience Matters in Enterprise GTM 15:17 How AI Is Changing Product Development 19:02 Building an AI-First, Enterprise-Ready Product 22:43 Why Handraise Isn't Chasing Hypergrowth 26:00 Matt's Favorite Book and Podcast 28:00 Where to Find Matt and Handraise Try Handraise: handraise.com

Forget Growth. Your Valuation Depends On Your AI Story | Tomasz Tunguz, GP @ Theory Ventures Tomasz Tunguz, General Partner at Theory Ventures, joins Sam Jacobs, AJ Bruno, and Asad Zaman with public software multiples sitting at 4 to 4.5 times forward revenue, down from the 100x ceiling of 2021. Topics include why the market now pays for an AI story rather than growth, the $10 billion AI companies committed in a single year to putting forward-deployed engineers inside customer orgs, and the 41 days a model company gets to commercialize a state-of-the-art release before it is knocked off the perch. Plus, why the mid-market is being abandoned for enterprise deals that close in 45 days, what quota inflation at AI-native companies is actually measuring, and a bull-versus-bear call on 50 to 100x multiples for AI harness companies twelve months from now. Key Takeaways: - The valuation follows the AI story, not the growth rate. Average public software trades around 4 to 4.5 times forward revenue today, and the category leaders carrying 30x and up are usually not the fastest growers in their category. As Tomasz put it: "what the market is asking for, and this is both true in the public and the private market, is great, you have an existing business, now show me that you can sell tokens." Revenue growth is still the highest single correlate to multiple, but the token story is what re-rates a company before the revenue shows up. - Before you copy an AI-native company's quota model, work out where the number is actually coming from. "It's not the supply side has changed and suddenly become 10x more productive. It's the demand side budgets have increased by a factor of 10. And that's what's driving quotas," said Tomasz. Quota-to-OTE ratios that topped out between 2.5 and 4 at Oracle and IBM five years ago are now routinely 1.5 at early startups, and a single insurance account can carry a quota in the tens to hundreds of millions, which is why he no longer grades companies on AE to SDR or AE to CSM ratios at all. - Using AI to save time is the wrong target for top-tier performance. Tunguz rebuilt his blog workflow so every edit runs through AI, and the total edit count held flat at 134 per post regardless of how long he had been at it, while a graded review of ten years of posts showed a 20% quality increase in 2026. "if you're a chess grandmaster and you want to be better with AI, you don't train less. You train just as much, but you hold yourself to a higher standard." The hour to an hour and a half per post did not change; the research, citations, and depth of analysis did. - Product advantage is thinning, so the distribution move is what investors are underwriting now. "the go-to-market innovation is now significantly more important than it was. And if you can find a founder who can execute a beautiful go-to-market judo move and produce a lot of leverage for the company, then it's incredible," said Tomasz Tunguz, General Partner at Theory Ventures, placing Dropbox, Zoom, Confluent, and HashiCorp as the previous era's version of the same pattern.  Connect with the Hosts & Guests: Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: Tomasz Tunguz, General Partner at Theory Ventures - https://www.linkedin.com/in/tomasztunguz/ Topline is more than a YouTube Channel: Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack Chapters: 00:00 Introducing Tomasz Tunguz 02:16 Market Stopped Paying For Growth 04:56 Show Me You Can Sell Tokens 06:33 Inside The Hugging Face Hack 10:07 Explaining RL With A Roomba 13:43 Is Security The Next AI Use Case 17:49 Fertility, Consumption, And Tokens 22:36 Overleveraged On The AI Buildout 26:08 Writing Every Post Through AI 30:55 The $10 Billion FDE Boom 39:11 FDE Moat Or Toll Booth 44:39 Quotas Are A Demand-Side Story 52:54 Does Customer Success Die 55:55 Enterprise Shift And GTM Judo 01:03:41 Bulls and Bears Sources & Attribution: 2015 quota figure: https://tomtunguz.com/how-big-should-your-sales-pipeline-be/ SaaS AE compensation: https://blog.bridgegroupinc.com/saas-account-executive-compensation 2024 AE metrics and compensation benchmark: https://blog.bridgegroupinc.com/2024-ae-metrics-compensation-benchmark AI investment map: https://www.forbes.com/councils/forbestechcouncil/2026/02/27/ai-is-redrawing-the-tech-investment-map-in-2026/ The $10B FDE Boom: https://tomtunguz.com/the-10b-fde-boom/ Clip: https://www.youtube.com/watch?v=8DbCQn86f9w Clip: https://www.youtube.com/watch?v=bSo4V6tY9XQ&t=1385s Clip: https://www.youtube.com/watch?v=36mE3cjYldU&t=560s

Evan Huck, CEO and co-founder of UserEvidence, opens up about the hard decision to shift from a tried-and-true outbound sales playbook to a long-term brand-building strategy. After eight straight quarters of flat pipeline growth, Evan had to trust the process, convince his board to stay the course, and rethink how UserEvidence reached its ideal customers. In this conversation, he shares what it takes to stay patient when results don't come fast, how to balance short-term pipeline needs with brand investments, and why the payoff was worth the wait. Evan also shares: - Why eight quarters of flat pipeline tested their commitment to brand over quick wins - How UserEvidence narrowed its ICP to unlock stronger growth - Why creative, one-to-one outreach can still break through with enterprise buyers - How Slack communities helped build credibility and generate early enterprise demand - Why product marketing came before demand generation in building the GTM engine - How customer advocacy became an increasingly powerful source of growth Chapters: 00:00 Introduction to Evan Huck and UserEvidence 04:31 From SDR to CEO: Evan's GTM Journey 07:54 Why UserEvidence Bet on Brand 09:31 Eight Quarters of Crickets: Waiting for Brand to Pay Off 12:30 Narrowing the ICP to Unlock Growth 13:51 The CEO Hustle Behind Enterprise Growth 16:00 Building Credibility Through Communities 18:00 Why the Right Team Matters 19:14 Why Product Marketing Came First 20:39 Turning Customers Into a Growth Engine 22:07 The "Chill, Humble" Leadership Philosophy 22:43 Evan's Favorite Book for Founders Try UserEvidence: userevidence.com

Keenan, founder and CEO of A Sales Growth Company and the bestselling author of Gap Selling, joins Sam Jacobs, AJ Bruno, and Asad Zaman to make the case that two companies with identical revenue can be valued 3 to 4 times apart, depending entirely on how that revenue got made. Topics include the four sales org archetypes (heroic, random, peacock, and compounding), the valuation discount investors quietly apply to revenue produced by heroics, why quota attainment fell from 60% to 23% while enablement spend went up 7x, and the difference between a sales system and sales structure. Plus, what revenue leaders can learn from how Sequoia, Blackstone, and CAA actually run their people, why Keenan is done with the phrase go-to-market, and the story behind the one-name brand.   Key Takeaways: - How you produce revenue changes what the market will pay for it: investors are buying your ability to repeat the number, not the number itself. Keenan puts a figure on it in his paper Not All Revenue Is Created Equal: "the discount could be as much as 15 to 20% discount on the valuation." Heroics hides the cost; nobody opens a CRM and sees "we closed a $2 million deal and nobody saw that that $2 million deal started at $2.6 million." - Systems are not structure. A system defines the outputs it wants and stays agnostic about how each rep gets there, which is what separates it from a script. "Making people do everything the same is structure," Keenan said. He runs it through golf: "I focus less on what your swing looks like, and I'm asking myself, are you able to hit a draw when you need to hit a draw?" - Sales teams over-invest in training the behavior (structure) and under-invest in understanding the buyer, which Keenan calls sales physics: "nobody buys anything unless their current state is untenable and intolerable." A good system helps the buyer realize that state, which will allow a deal to close. - The spending trend is going the wrong way, and Keenan closes the episode with the numbers: "In 2012, depending who you ask, 60% of reps made quota… now 23%… And the spend has gone up 7x… But win rates declined by 29%. Sales cycles extended by 37 days… What we're investing in isn't working." It persists because no CRO gets room to rebuild: "It's the boat's got a hole in it… You got to fix it. But by the way, you cannot dry dock the boat." And yes: AJ Bruno is buying the book for the first 20 listeners who reach out. Send AJ a direct message on LinkedIn or in the Pavilion Topline Slack and he will buy you a copy of Gap Revenue Performance.   Connect with the Hosts & Guests:   Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: Keenan, CEO & Founder at A Sales Growth Company - https://www.linkedin.com/in/jimkeenan/   Topline is more than a YouTube Channel:   Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack   Chapters: 00:00 Introducing Keenan And Gap Selling 03:08 A Dollar Of Revenue Is Not A Dollar 03:46 The Four Sales Org Archetypes 06:59 The 15 To 20% Valuation Discount 08:58 The MEDDIC Definition Problem 12:47 The Left Tackle Analogy 18:24 Can Heroics Be Predictable? 23:10 Structure Is Not A System 28:32 What VC Firms Get Right 42:09 The Physics Of Selling 50:16 Awareness First, Then Pipeline 51:55 Tired Of The Word Go-To-Market 1:00:23 AI, Product Velocity And Enablement 1:04:26 Is Sales A Power Law? 1:12:09 The Story Behind One Name

Bryan Murphy, CEO of Smartling, confronts a $40 billion industry stuck in the slow lane—the world of translation. Most companies still handle translations like it's 1999: manual, expensive, and painfully slow. Bryan saw AI as the game changer that could rewrite the rules, but integrating it wasn't a walk in the park. He shares how Smartling harnessed AI to not just cut costs and speed up translation but to finally boost quality close to human-level precision without losing control over brand voice or nuance. Yet, making this leap meant upheaval: reorganizing teams, hiring AI experts, and establishing ruthless R&D discipline to separate winning ideas from distractions. Bryan also shares: - Why a $40 billion translation industry was ripe for disruption - How AI helped Smartling move from faster and cheaper to dramatically better - What it took to bring AI into a traditional business without sacrificing quality or brand voice - Why hiring the right AI talent was critical to making the shift - How ruthless R&D discipline helps separate breakthrough ideas from distractions - Why every AI initiative needs a clear connection to customer outcomes Chapters 00:00 - Introduction to Bryan Murphy and Defining the Translation Challenge 02:30 - The Hidden $40B Translation Market and Its Untapped Potential 06:00 - Early AI in Translation: Faster and Cheaper, But Not Yet Better 09:20 - Human-in-the-Loop AI: Boosting Translator Productivity Tenfold 13:00 - Unlocking Market Expansion Through Improved SEO and Digital Footprint 15:00 - The Moment of Truth: Recognizing GPT's Impact and Rolling Out Rapid Innovation 18:00 - Overcoming Organizational Challenges: From Excitement to Structured Execution 22:00 - The Discipline of "Customer-First" in AI Development and Roadmapping 24:00 - Leadership Lessons: Listening Without Losing Vision Amidst Painful Change 26:00 - Winning Customer Trust: Betting On Proofs of Concept Against Skeptics 28:00 - Personal Insights: Favorite Leadership Books and the Role of Intellectual Curiosity 33:00 - Wrap-up and Invitation to Follow Smartling's AI-Empowered Evolution Try Smartling: smartling.com

The Unwritten Rules of CRO Survival | Rick Smolen, CRO @ ShipHero Rick Smolen, CRO of ShipHero and sales advisor to Riverwood Capital's portfolio of more than 2 dozen enterprise software companies, joins Sam Jacobs, AJ Bruno, and Asad Zaman to argue that AI is leverage rather than a shortcut. Topics include why AI note-takers quietly degrade seller performance, why ShipHero has not raised a single quota despite real AI investment, and why the leading AI companies keep hiring classic enterprise CROs. Plus Rick's scorecard for judging revenue leadership beyond the number, an honest conversation about getting fired, and a bull case for HubSpot. In short... big episode! Key Takeaways: - AI widens the gap between the best and worst sellers instead of lifting everyone, and Rick Smolen, CRO at ShipHero, frames it in financial terms: "It's like debt... debt is leverage. It can make performance exceptionally good, or it can bankrupt you." His prediction is that the strongest performers get 10x better while the weakest become "unmistakable and hard to hide." - Outsourcing note-taking to an AI tool costs sellers the exact signal that closes enterprise deals. As Rick put it: "the computer can't capture the tone, can't capture the nuance, can't capture the content." His warning to any rep who treats it as time saved: "when a seller is going to say, oh cool, I don't have to do note-taking anymore, like their performance is going to go backwards." - The 3-to-5x rep productivity story does not survive contact with an enterprise sales cycle. Despite meaningful AI investment and measurable conversion-rate gains, Rick reports that at ShipHero "we have not raised quotas on anybody on the team," adding that "I don't believe that if I was to double somebody's quota that I give them any chance to be successful." - The AI-native companies scaling fastest are staffing go-to-market with the most traditional enterprise leaders available. Asad Zaman, CEO at STA, walks through the CRO hires at OpenAI, Cursor, Factory, and Anthropic and lands on the pattern: "we're back to like, let's just hire John McMahon's disciples and let them run at the market." Connect with the Hosts & Guests: Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: Rick Smolen, CRO at ShipHero - https://www.linkedin.com/in/ricksmolen/ Topline is more than a YouTube Channel: Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack Chapters:  00:00 Introducing Rick Smolen 02:37 AI Is Not Good Or Bad 05:19 The AI Slop Email Mystery 08:25 AI Note-Takers And Lost Nuance 12:01 The Best Get Better, The Rest Worse 15:24 The Soft Part Of Enterprise Sales 18:24 Can Reps Be 5x More Productive? 23:09 Have Quotas Gone Up At ShipHero? 26:48 Why AI Firms Hire Classic CROs 30:48 What Is Driving Pipeline Now 49:37 Leadership In A Confused World 56:44 Should A CRO Jump Ship? 59:35 Have A Plan, Not Excuses 1:06:08 Bulls And Bears: HubSpot 1:09:32 Vibe-Coded Demos And FDE Teams

Mike Carpenter — CEO of Xfactor.io, former President of Global Sales at CrowdStrike — didn't win VP of the Year seven out of eight times by outworking everyone. He did it by finding cheat codes in the data everyone else was ignoring. In this episode, he walks through the X-Factor methodology: how he staffed ops teams that were abnormally large by industry standards, how he cut rep ramp time from 18 months to 90 days by warming territories before a new hire ever showed up, and why he thinks most companies running AI on their CRM are getting confident, wrong answers and won't know it until the numbers drop. Mike also shared: - Why working harder isn't the same as finding an X-Factor - How he used data to uncover the hidden patterns that drive revenue - Why static operating plans break down as businesses scale - How he cut sales ramp time by warming territories before reps entered them - Why causal AI matters more than simply putting an LLM on your data - What it takes to build AI that leaders can actually trust Chapters 00:00 Intro 00:33 Meet Mike Carpenter and Xfactor 04:11 The "X-Factor" mindset that drove 25 years of sales success 08:18 Why working harder isn't a sustainable competitive advantage 10:56 The planning problem that inspired Xfactor 14:57 How AI uncovers hidden revenue opportunities 18:20 Why MQLs are the wrong metric to optimize 23:12 The biggest mistake companies make with AI today 25:52 Where to find Mike and Xfactor Try Xfactor: xfactor.io/

Enterprise account executives are now signing for $200,000 salaries, $200,000 variable comp plans, and up to half a million dollars in equity at sign-on. Meanwhile, offer acceptance at the top AI companies sits at 45% and half of the 38,000 startup sales reps in San Francisco and New York have taken a new job in the last two years. In this episode, Sam Jacobs, AJ Bruno, and Asad Zaman go hosts-only on why the sales talent market broke, what QuotaPath's compensation data across more than 1,400 companies says about quota attainment splitting into a barbell, and why Paul Graham calling go-to-market bogus says more about Silicon Valley's blind spot than it does about sales. Plus, where young sellers still get their start, whether a CRO can be great without ever carrying a bag, why go-to-market cannot rescue a company that has lost product-market fit, and what HubSpot's 20% stock drop signals for every SaaS business trying to make the AI transition. Key Takeaways: - The AI buildout has drained the two talent pools it depends on, and compensation is repricing in real time. As Asad Zaman, CEO of STA, described the enterprise AE market: "Enterprise account executives now get paid $200,000 salaries, $200,000 variable comp plans, up to half a million dollars in equity at sign-on. That used to be $150,000 to $175,000 at the top end, just like a year and a bit ago." With 38,000 startup software sellers in San Francisco and New York and a quarter of them changing jobs in the last twelve months, the constraint on AI companies hitting escape velocity is no longer capital, it is people. - The jobs data cuts against the automation narrative. Sam Jacobs, CEO of Pavilion, pointed to the Philippines outsourcing sector, 8% of that country's GDP, where employment in IT and business outsourcing is up 20% to 1.9 million workers and industry revenue is up 30% to $42 billion since the launch of ChatGPT: "I just think, you know, it's Jevons' paradox. It is what happens with every new piece of technology. Everybody thinks the technology is going to wipe everybody out, and instead the economy adapts." Companies are leaner per dollar of revenue and still cannot hire fast enough. - Quota attainment is no longer distributed the way comp plans assume. QuotaPath's first-half numbers put 58% of AEs on track against annual quota versus 55% a year ago, but as AJ Bruno, CEO of QuotaPath, explained, the shape underneath moved: "the standard deviation is way higher this year. Meaning that the winners are going to be winning more … So it's more like a barbell than it is a bell curve." At some AI companies two reps out of ten are closing half the entire number, which breaks the capacity math most sales leaders use to set targets. - For individual sellers, the window matters more than the title. Asad Zaman's advice to reps weighing a step up into leadership: "this is the moment where you can make millions of dollars right now … So don't make silly choices … Become a leader later. Go make money right now." He now benchmarks offers on whether 300% of plan clears a million dollars, and warns that private equity portfolio companies that never gave equity to individual contributors are losing these candidates outright. Connect with the Hosts: Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Topline is more than a YouTube Channel: Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack Chapters:  00:00 Three Hosts, Three Topics 02:19 The Talent Market Has Gone Crazy 05:42 $200K Base, $200K Variable 09:00 AI Was Supposed To Kill Sales 15:16 Go Make A Million Right Now 16:53 Where Young Sellers Get Their Start 23:20 Build A University Inside The Company 31:58 Paul Graham Versus Go-To-Market 36:22 Why YC Misses Enterprise Software 40:55 Can A Non-Seller Be A Great CRO? 44:42 GTM Cannot Fix Product-Market Fit 49:30 One To Ten To A Hundred 53:38 Quota Attainment Is A Barbell 1:02:41 The HubSpot Nightmare 1:06:05 Falling Back In Love With The Business

Jaleh Rezaei, Co-founder and CEO of Mutiny, joins Sam Jacobs, AJ Bruno, and Asad Zaman to explain how she deprecated a thriving 8-figure SaaS business in November 2025, shipped a private preview in February, and GA'd an AI-native product in April that is now used by more than 3,500 organizations including Snowflake, Rippling, Uber, and GitLab. Topics include why running a scaled SaaS business and a zero-to-one AI bet at the same time proved impossible, how to price and defend AI credit consumption when a $5,000 design project now costs 50 credits, and the shift from sales-led outbound to product-led growth for enterprise go-to-market. Plus, why brand is one of the few remaining moats in B2B, an AI raccoon launch video that fooled (some of) the panel, and a bulls-versus-bears debate on quota attainment, AI note-takers, and whether salespeople will ever spend 85% of their time selling. Key Takeaways: - Make the hard decisions FAST. As Jaleh Rezaei, CEO and Co-founder of Mutiny, put it: "I definitely would've said the job of the CEO is you have to make the hard calls. But what I learned in that experience is that it's actually about making the hard calls really fast, which means that you're getting there before everybody else on your team is there." Her test for founders weighing a similar bet is a single question: "is there one really hard decision, maybe one that scares the hell out of you that you don't want to do, that you can make that would make 50 subsequent downstream decisions a lot easier for your company?" - AI budgets get cut because vendors let buyers anchor on the credit bill. Instead, they need to help buyers see the value of the work the credits replace. Jaleh Rezaei, CEO and Co-founder of Mutiny, reframed it with her own before-and-after: "I used to have a designer that I paid $5,000 to, and it would take 2 weeks of back and forth, and I paid $5,000 to get to something that I was pretty happy with. But end to end took a month. Now in 6, 7 hours, I can build that in Mutiny, and maybe that does cost me 50 credits. That's really freaking cheap relative to what I used to pay that designer." She argues the vendor has to build the ROI case for the customer, per rep, or budget conversations default to minimizing every AI bill. - Brand is a durable moat in B2B mostly because so few companies are willing to pay for it in risk. According to Jaleh Rezaei, CEO and Co-founder of Mutiny: "great brand comes when you marry deep customer knowledge and a willingness to take risk … a lot of times people that own brand they don't necessarily either have the deep customer knowledge or they don't have the ability to take that kind of risk inside of the company." Her internal standard is blunt: "anything we do on marketing, like, if it's not different, just stop doing it. It's just not going to matter." - Quota attainment is snapping back hard, and the data has not caught up to the narrative. AJ Bruno, CEO of QuotaPath, brought Q2 numbers to the bulls-versus-bears round: "I just looked at Q2 numbers and they're trending wildly back up. We're actually, the average quota attainment for a QuotaPath customer was 76% in Q2." Asad Zaman pushed back that a jump from roughly 40% to 76% in a single quarter reads more like a bubble signal than a sudden improvement in selling, and AJ offered to run a comp study with Pavilion on the data. Connect with the Hosts & Guests: Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: Jaleh Rezaei, CEO & Co-founder at Mutiny - https://www.linkedin.com/in/jalehr/ Topline is more than a YouTube Channel: Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack Chapters: 00:00 Introducing Jaleh Rezaei 04:00 Can SaaS Era Companies Go AI Native? 05:01 From Gusto To Founding Mutiny 07:00 When AI Became A Reasoning Engine 11:28 Why Running Two Products Was Impossible 13:32 Shutting Down An 8-Figure Business 16:18 Winning Formula: Speed, No Backup Plan 20:17 The Hard Months After Deprecation 24:47 Acute Pain Versus Chronic Pain 29:17 CEO Has To Be The Bad Guy (Sometimes) 37:17 AI Margins And Credit-Based Pricing 40:10 A $5,000 Deck Versus 50 Credits 47:03 Sales-Led To PLG For Enterprise 50:37 Brand As The Remaining Moat 1:00:34 Bulls and Bears