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Russ Mikowski, CEO of SurePeople and longtime revenue leader in tech, never planned to become a CEO. Recruited to lead a 10-year-old company into its next stage of growth, he faced technical debt, an unfocused ideal customer profile (ICP), and the challenge of turning the company's potential into a scalable business. In this episode of Topline Spotlight, Russ joins Sam Jacobs and AJ Bruno to discuss the decisions behind SurePeople's transformation, including rebuilding parts of its product, narrowing its target market, and resisting custom requests that could pull the business off course. Russ talks about: - How to identify and focus on the customers your product serves best - When rebuilding is a better option than refactoring - Why saying no to the wrong opportunities can protect long-term growth - How to keep a team aligned through organizational change - Why great leaders attract and retain talent by removing obstacles Chapters 00:00 Introduction to Topline Spotlight 01:54 Meet Russ Mikowski, CEO of SurePeople 03:00 SurePeople and the PRISM Assessment 05:51 Russ's Journey to CEO 08:55 Tackling Technical Debt and Rebuilding the Product 12:01 Narrowing the ICP and Finding Market Focus 14:50 Communicating Change and Aligning the Team 17:53 Leadership Lessons from a Mentor 24:00 Where to Find Russ Mikowski and SurePeople Try SurePeople: surepeople.com

Michael Walrath, CEO of Yext, is back on Topline to explain how Yext went from breakeven to 31% EBITDA margins on an 80% gross margin business, after halving its headcount and using its balance sheet to buy back roughly 35% of every share it ever issued. He joins Sam Jacobs, AJ Bruno, and Asad Zaman to argue that the old rules of business still apply: why VC math and founder math are different games, why employees lose the most when an overvalued startup like Airtable lands far below its peak valuation, and why this market feels like 2004. Plus, why Yext stopped doing earnings calls and replaced most stock comp with cash, why cutting the bottom half of a sales team can raise bookings, and how Yext is blurring the lines between AEs, account managers, CSMs and sales engineers. Key Takeaways: - Real profitability turns any growth into fuel. As Michael put it, "when you're actually profitable, like really profitable, then any growth becomes hugely accretive." With 80% gross margins and 31% EBITDA margins, "Every incremental dollar, I can spend 45 cents of it and not affect my margins in any way," so a left-for-dead software company can fund its own growth whatever the market says it's worth. - Chase growth only where it actually exists. "Nothing's more powerful than growth at creating value. Nothing is more destructive to value than chasing growth when the growth isn't there," said Michael. Airtable avoided the trap by leaving its cash on the balance sheet, while Yext once spent 74% of revenue on sales and marketing into a declining growth rate. - Cutting your weakest sellers can grow bookings. When 20% of reps make quota and the bottom half brings in 20% of bookings, the spreadsheet says cutting them costs you that 20%. "It's not even close to true. It's the opposite," said Michael (his numbers were illustrative). Yext now has fewer, better sellers, and is "effectively eliminating all distinction between go-to-market roles" in favor of teams that own books of customers. - Stock comp can turn your own employees into sellers of your stock. Most people sold their RSUs the day they vested, and every quarterly issuance meant the company sold shares to cover taxes too. "The last thing you need are more sellers of your stock every quarter," said Michael, so Yext now pays most employees more cash and points long-term believers to its employee stock purchase plan. 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: Michael Walrath, CEO at Yext - https://www.linkedin.com/in/michael-walrath-b63166/ 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 Mike Walrath 03:13 VC Math vs Founder Math 04:46 Why Employees Lose the Most 09:05 Why This Market Feels Like 2004 12:04 31% EBITDA Makes Growth Accretive 16:12 Why Mike Is a Jobs Bull 19:48 What Airtable Got Right 28:19 Hot Startup Equity Is a Lottery 41:37 Yes, You Can Attract Talent 44:16 The Road to 30% EBITDA Margins 47:45 No Earnings Calls, No IR Team 51:52 Replacing Stock Comp With Cash 54:41 Cut the Bottom 50% of Sellers 57:19 Collapsing Go-to-Market Roles 01:01:22 From PE Guy Back to Growth

When Rick Smolen stepped into the CRO role at ShipHero, he took on responsibility for the entire customer lifecycle, from marketing and partnerships to customer success and support.  With a background primarily in sales, he had to learn how to lead functions outside his expertise without needing to have all the answers. In this episode, Rick joins Sam Jacobs to discuss the leadership lessons that came with that transition, from asking better questions to building trust with his team. He also explains how to learn from failure, navigate setbacks, and focus on what you can control as a leader. Rick talks about: - Why curiosity makes you a stronger cross-functional leader - How to challenge your team without micromanaging - Why experimentation requires accepting failure - What leaders should focus on when business results fall short - How to prioritize important work that rarely feels urgent Chapters 00:00 Introduction to Rick Smolen and ShipHero 01:10 What ShipHero Does 05:14 Rick's Career Journey 07:50 From Sales Leader to CRO: The Biggest Shift 10:49 Why Curiosity Makes You a Better Leader 16:23 Building a Leadership Team That Learns and Experiments 17:54 Evaluating Leadership Beyond Revenue 22:50 Rick's Book Recommendation: The 7 Habits of Highly Effective People 24:53 Where to Find Rick Smolen Try ShipHero: shiphero.com

Amy Konary, Founder & Chair of The Subscribed Institute at Zuora, coined the term SaaS as an IDC analyst around 2000, when her first forecast sized the whole market at $40 million. She joins Sam Jacobs, AJ Bruno, and Asad Zaman for the first in-person Topline to ask whether AI company economics are a house of cards, and whether circular financing and double counting are real problems. Plus, why POCs have stopped being a pipeline signal, experimental revenue versus true ARR, a new leverage index for sticky revenue, tokens versus credits, and how close outcome pricing can really get. Key Takeaways: - Treat POCs as a weak pipeline signal. As Amy put it, "it used to be that hands-on product was a really good signal from a pipeline perspective, but everyone's doing POCs just to kick the tires, but actually has no mandate to buy." Many are free, production-ready builds, and very few convert. - Usage alone won't tell you which revenue will last. Amy scores customers on scope and workflows, trust in the system's outputs, and how much of their own context they upload, because "you can have 2 customers with the exact same usage, but very different leverage." Low leverage means "That revenue is less durable." - Pure usage pricing can leave you as exposed as seats did. "If you're just tracking usage, and usage is highly experimental, and usage decreases over time as people optimize the tools, you're in the same vulnerable position you were in with seats," said Amy, who expects hybrid models with a smaller, trackable outcome piece. - Build for durability without rigidity. "So I think there's a difference between durability and rigidity," Amy said, and her metaphor is bamboo: one of the strongest construction materials, yet flexible, anchored by a clear focus on the customer's progress. 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: Amy Konary, Founder & Chair, The Subscribed Institute at Zuora - https://www.linkedin.com/in/amykonary/ 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 Amy Konary 01:43 From ERP Sales to Industry Analyst 03:33 How Amy Konary Named SaaS 08:03 How Salesforce Taught the Street SaaS 10:31 Building Durable Companies for AI 11:52 Does Gross Margin Still Matter? 15:10 Who Is Checking AI Company Math? 17:03 Circular Financing and Double Counting 18:30 Is AI a House of Cards? 21:49 Durability Versus Rigidity 29:19 Be Careful About Your POCs 33:40 The Leverage Index for Sticky Revenue 39:12 SaaS Companies Moving Into Services 41:59 Tokens, Credits and Outcome Pricing 48:32 P(doom) and Raising Kids With AI

When Sam Jacobs founded Pavilion, formerly Revenue Collective, he set out to build a private community for operators in a startup world that traditionally celebrated founders and overlooked the people running the business. But as Pavilion grew to 10,000+ members, the very thing that made the community valuable began to get diluted. In this special Topline Spotlight episode, Sam joins co-hosts AJ Bruno and Asad Zaman to talk about what happened, why removing the qualification barrier was a mistake, and what it took to bring Pavilion back to its original vision. Sam talks about: - Why rapid growth can dilute what makes a community valuable - How LinkedIn and Slack helped Pavilion scale faster than expected - What happened when exclusivity gave way to openness - Why reversing course became harder once the community had grown - The importance of having a long-term vision instead of chasing immediate growth - Why building something great requires patience and restraint Chapters: 00:00 Introduction 00:42 Business Challenge of the Last 24 Months 01:29 What Is Pavilion? 02:43 Launching Pavilion Gold 04:01 Why the Community Scaled So Quickly 06:51 LinkedIn and Slack as Growth Drivers 07:02 Shifting Culture of Openness Among GTM Leaders 08:04 The Consequences of Losing Focus 10:54 The Biggest Mistake: Removing the Qualification Barrier 11:32 The Challenge of Reversing Course 13:46 Continued Opportunity for Operator Advocacy 15:00 Solving the Challenge: Long-Term Vision 15:54 Building a 3-Year Vision for Pavilion 16:08 Importance of Patience in Building Exclusive Communities Try Pavilion: joinpavilion.com

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