Topline

The #1 podcast for founders, operators, and investors in B2B tech. Tune in every week to hear Sam Jacobs, AJ Bruno and Asad Zaman discuss and debate the trends, news, and developments impacting the B2B tech world. Enjoy the hot takes, strong opinions, and dry humor.

SPOTLIGHT: He Said No to Bad-Fit Customers. Growth Got Better. | Snehal Nimje, CEO & Co-Founder @ Outdoo 08/13/2026

The (Painful) Pivot To AI-Native: What They Don't Tell You | CEO @ Mutiny, Jaleh Rezaei 08/09/2026

The (Painful) Pivot To AI-Native: What They Don't Tell You | CEO @ Mutiny, Jaleh Rezaei 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 /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/42364285

Meet The World's Most Advanced AI Sales Team | Amanda Kahlow, Founder & CEO @ 1mind 08/02/2026

Meet The World's Most Advanced AI Sales Team | Amanda Kahlow, Founder & CEO @ 1mind Amanda Kahlow, Founder & CEO of 1mind, joins Sam Jacobs, AJ Bruno, and Asad Zaman to break down how an AI-powered solutions engineer named Nigel took 33% of the talk time in a two and a half hour enterprise meeting and produced a $278,000 deal. Topics include why AI aimed at efficiency gains misses real revenue impact, Amanda's prediction that marketing, sales, and customer success collapse into one function within 12 months, and why AI adoption has to be top-down instead of bottoms-up. Plus, the 15 agents running behind every superhuman, a 98% accuracy bar measured by live evals, whether agents will negotiate with other agents on the buy side, and a bulls versus bears round on Salesforce, sales dinners, and the health of the average go-to-market team. Key Takeaways: - Most go-to-market teams are pointing AI at the wrong layer. Better forecasting, faster research, and cleaner dashboards make the people you already have marginally more productive, which is not where the revenue is. As Amanda Kahlow, Founder & CEO at 1mind, framed it: "My thesis is that buying and selling happens in the conversation." Everything built around the conversation to enable a seller is, in her words, yesterday's workflow. - Trust, not novelty, is what moves an enterprise deal. Amanda flew a red-eye to Austin for a second meeting with a CPO and CMO, brought a superhuman named Nigel on screen, and watched the room turn to the AI for depth even she could not provide. As she told it, "the CPO was like, Amanda, shut up, basically. I wanna talk to Nigel." The meeting scheduled for an hour ran two and a half, and produced "a $278,000 deal from one in-person meeting going through procurement in one week". Her read on why it worked: "People say people buy from people. You buy when you trust." - The human face on an AI agent is a click-through device, not the value. Amanda's verdict after a year of selling them: "The face is a novelty." 1mind drops the face entirely on live calls because the movement distracts. The important part is the conversational AI, where "each superhuman has roughly 15 agents working behind the scenes." One handles small talk, another loads the live demo, another builds the perspective slide a human seller would normally take a week to produce. - Bottom-up AI adoption is where the value leaks out. Amanda's pushback on the idea that people who use AI will simply eat the people who do not: telling every individual to go be more efficient produces slop and no measurable gain, while the real impact, in her words, "is going to come at the top down when we think about restructuring the org". 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: Amanda Kahlow, Founder & CEO at 1mind - https://www.linkedin.com/in/amandakahlow/ 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 Amanda Kahlow 00:59 Building Superhumans At 1mind 03:24 Why Efficiency Gains Miss The Point 06:04 GTM Functions Collapse In 12 Months 08:48 The Ghost Note Debate 15:20 Nigel Takes 33% Of Talk Time 20:41 The Face Is Just Novelty 22:27 Fifteen Agents Behind One Superhuman 38:46 Compute Costs And AI Margins 41:19 How Accurate Are AI Agents? 47:08 Positioning An AI Company 52:13 When Agents Negotiate With Agents 53:54 Will CSM Jobs Survive? 57:56 Bulls and Bears 1:06:15 Boards, 6sense, And Burnout /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/42284330

SPOTLIGHT: AI Is Making Sales Reps 60% Faster to Revenue | Justin Shriber, CEO & Co-Founder @ Terret AI 07/28/2026

World’s #1 Banking CMO: How AI Is Changing Billion Dollar Banks Today | Tim Rutten, CMO @ Backbase 07/26/2026

World’s #1 Banking CMO: How AI Is Changing Billion Dollar Banks Today | Tim Rutten, CMO @ Backbase Tim Rutten, CMO of Backbase, the €2.5 billion Amsterdam tech company whose AI-native Banking OS powers 120+ banks worldwide, joins Sam Jacobs, AJ Bruno, and Asad Zaman with the clearest AI ROI numbers we have heard on the show: double the pipeline on 25% less budget. Topics include the custom go-to-market operating system his team built on the Vercel stack, why real bank deployments are 99% deterministic, the 90% cost reduction banks are finding in customer care, and why most enterprise workloads do not need frontier-model intelligence. Plus, where the AI bubble breaks, what happens to judgment and taste when anyone can generate output, and a bulls-versus-bears round on LinkedIn, banking apps, and sales spiffs. Key Takeaways: - Backbase's marketing org runs on GTMOS, a custom go-to-market operating system built on the Vercel stack and wired into Salesforce and the company's finance tools, and the numbers behind it are specific. As Tim Rutten, CMO at Backbase, put it: "Double the pipeline, 25% head cut on my budget... So with 25% less budget, I'm actually still doubling the pipeline." The unlock came from rebuilding how the team works rather than layering tools on top of it. - Shipping AI into a regulated industry means using AI more narrowly than you might expect. On what real bank deployments look like, Tim Rutten said: "the actual implementations are almost 99% deterministic, and there's this one little percent that actually gets them to gain, to reason at the right moment in time." That same architecture caps the bill, because most banking workloads are repetitive and rule-bound. But the same rigor can net fantastic results from AI in broader applications as well. - Backbase treats AI slop as an architecture problem, containing content generation inside hard boundaries. Per Tim Rutten: "You have tone of voice, you have guardrails that we don't have AI slop. There's like 22 rules that are applied. If they don't check out, the agent needs to rewrite and continuously learns to rewrite." The human half of the risk is harder to engineer around, as Asad Zaman, CEO of Sales Talent Agency, framed it: "a lot of people that didn't have a skill are using AI for that thing. And if you didn't have a skill in an area or judgment or taste in that particular area, you have no mechanism to stress test the quality of what is coming out." - On how the AI bubble pops, Sam Jacobs, CEO of Pavilion, put the risk on the business model sitting underneath the capex: "if everybody presumes the way that all these companies make money is selling tokens… and then all of a sudden it turns out selling tokens is a really terrible business. Well, then that's a thing that would compress." Tim Rutten lands in a similar place on timing while staying long on the outcome: "a little bit bearish on timing, massively bullish on the future… it will happen nevertheless, but it's going to be a very rocky ride." 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: Tim Rutten, CMO at Backbase - https://www.linkedin.com/in/timrutten/ 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 Tim Rutten 03:11 Inside Backbase And 120 Banks 09:42 90% Cost Cuts In Call Centers 12:04 Why The Application Layer Wins 15:23 Europe, The US, And Regulation 21:50 Where The AI Bubble Breaks 27:24 Why Banks Skip Frontier Models 34:34 Bank Budgets Shift To AI Native 38:23 Real ROI At Lloyds And JPMorgan 44:31 Quiz Pro Quo 49:37 GTMOS, The Go To Market OS 52:02 Double Pipeline On 25% Less Budget 53:53 Judgment, Taste, And AI Slop 1:06:15 Real Time Marketing By Christmas 1:09:30 Bulls and Bears /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/42215360

SPOTLIGHT: Why 80% of B2B Buying Happens Without You | Alexander Kesler, CEO @ INFUSE 07/24/2026

SPOTLIGHT: Why 80% of B2B Buying Happens Without You | Alexander Kesler, CEO @ INFUSE Buyers stopped picking up the phone. They research on their own, ask their peers, and now they ask AI which vendors to consider before a single salesperson ever hears about it. So where does that leave marketers? Sam Jacobs sits down with Alexander Kesler, founder and CEO of Infuse, to break down the dark funnel and what it means for B2B demand gen right now. They get into why most of the buying journey happens before you're ever contacted, how AI tools are generating "day one" shortlists on the spot, and why the real game is earning a spot on the day zero shortlist — the vendors a buyer already trusts no matter what ChatGPT says. Alex has spent 25+ years building companies across marketing, media, and data, and is the author of two books on B2B marketing best practices. His advice for marketers comes down to one thing: stay flexible, read the research, and build the relationship before the buyer is in market. What we get into: Why the traditional B2B sales funnel no longer reflects how today's buyers actually buy What the Dark Funnel is and why 80% of the buying journey happens before prospects contact sales The difference between Day Zero and Day One shortlists and why every marketer needs to understand both How AI and Generative Engine Optimization (GEO) are reshaping vendor discovery Why building trust and thought leadership before buyers are in-market is the new competitive advantage Alex Kesler's advice for modern B2B marketers on staying relevant in an AI-first world Chapters: 00:00 Intro 00:36 Meet Alex Kesler and Infuse 03:10 The dark funnel explained 05:16 Why buyers don't want to talk to sales anymore 08:07 The AI buying journey and Day One shortlists 11:28 GEO: Winning recommendations from AI search 14:07 Day Zero vs. Day One: The new marketing playbook 16:06 Marketing 101 is making a comeback 16:27 Why ABM can limit your growth 17:35 The #1 trait every modern B2B marketer needs 19:20 Alex's leadership philosophy: Do the right thing 20:36 Where to find Alex and Infuse Try Infuse: infuse.com /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/42129470

SPOTLIGHT: The AI category GTM teams are about to converge on | Adam Liska, CEO & Co-Founder @ airspeed 07/21/2026

SPOTLIGHT: The AI category GTM teams are about to converge on | Adam Liska, CEO & Co-Founder @ airspeed A rep says "follow up on that" on a call, then buries it under five more calls and a late-night inbox. Three days later the deal's gone cold, but the CRM still says it's live. The manager forecasts off that. The CRO forecasts off the manager. The board asks the CEO if anyone actually has a grip on the number. The whole thing was built on a promise nobody kept. Adam Liska worked on the early Gemini models at Google DeepMind before leaving to close that gap. His company, airspeed, just raised a $20M Series A on a bet that "revenue execution" is the next real category, not another tool that logs calls and calls it intelligence. Sam Jacobs traces the full arc with him: DeepMind to founder-led sales to the unglamorous work of turning a founder's instincts into a system a team can actually run. What we get into: Why "follow up on that" breaks the forecast chain from rep to CRO to board What "revenue execution" means, and why it isn't revenue intelligence with a new label Whether you own the interface or hand it to a chat model and live as middleware The Nashville lunch that became airspeed's first six-figure deal The real sequence from founder-led to scalable: capture the data first, then build the playbooks Owning your data instead of renting Salesforce's architecture The modern Turing test, AI-native orgs, and where the back office is headed Chapters: 00:00 Intro 00:44 From DeepMind to airspeed, and the $20M Series A 01:30 "Follow up on that" — the execution gap that breaks forecasts 04:00 What category is this? Revenue execution, defined 05:40 Headless vs. owning the interface 08:00 The origin story: leaving DeepMind in 2022 11:39 Founder-led sales and the Nashville lunch that closed a six-figure deal 13:18 The hard part: turning founder-led into a repeatable system 14:14 Why they recorded everything from day one 16:35 Owning your data, and where the source of truth lives 19:03 The playbook: data first, then hierarchical playbooks 20:52 Influences: the modern Turing test and AI-native orgs 23:37 Where to find airspeed Try airspeed: goairspeed.com /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/42129370

AI Marketing Master: The ‘AI CMO’ is a Beautiful Lie | Marc Ferrentino, CEO @ Quotient 07/19/2026

AI Marketing Master: The ‘AI CMO’ is a Beautiful Lie | Marc Ferrentino, CEO @ Quotient Marc Ferrentino, Co-Founder and CEO of Quotient and former chief technical architect at Salesforce, joins Sam Jacobs and Asad Zaman to separate AI-marketing hype from what actually works today. Marc's core claim: the 'AI CMO' is marketing fiction, and the real near-term unlock is clearing the roughly 70% of a marketer's day lost to busywork, so smaller teams can finally operate like big ones. Topics include the collapse of specialized marketing roles into cross-functional generalists, why the apprenticeship model that trained classic marketers is most at risk, where the durable edge moves as performance marketing gets automated... and how taste separates real work from AI slop. Plus, a Quiz Pro Quo trivia round on famous tech emails, an honest look at ageism facing marketers in their 40s and 50s, and a Bulls and Bears debate on legacy martech, HubSpot, and Figma. Key Takeaways: - Marc's near-term promise to marketers is not an AI CMO but the removal of busywork. As he puts it: "companies that come out and claim to be your AI CMO… I think that is the most misleading marketing, but it's also just not true." Buckle up for a story or two about how he's seen the "AI CMO" blow up in people's faces. - The hiring bar is shifting from raw craft to AI fluency. In Marc's words: "we're all looking for the 10x developer, but the 10x developer who knows how to use AI is a 100x developer. And so it's the same thing with the marketer… the marketer who knows how to use AI is a 100x marketer… That's the person we want on the team." And he shares how his own developer interviews changed to match. - Marketing roles are not disappearing, but the specialist ladder that trained seasoned marketers is eroding. As Sam Jacobs, CEO of Pavilion, put it: "I see the collapse of specialization within a particular function. That doesn't diminish the need for the function, but does create an opportunity for those that are more fluent in all of these cross-functional tools." His deeper worry is the pipeline: "the apprenticeship model is the thing that's most at risk," raising the prospect of "a lack of classically trained marketers." - Ageism is real in marketing hiring, and it often hides inside neutral-sounding language. Asad Zaman, CEO of STA, observed, clients are saying things like: "I'm looking for somebody with high energy. High energy is like, I need somebody who is 30 to 33… high energy is like an age, basically." To what extent do the hosts agree with this perspective? Only one way to find out... Connect with the Hosts & Guests: Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: Marc Ferrentino, Co-Founder & CEO at Quotient - https://www.linkedin.com/in/marcferrentino/ 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 Marc Ferrentino 02:09 Where AI Actually Works Today 04:05 The 'AI CMO' Is a Lie 07:10 AI Multiplies, Not Replaces 12:11 The Collapse of Specialization 15:10 The Apprenticeship Model at Risk 16:11 The Real Edge Is Brand 21:18 AI Slop and the Taste Problem 23:02 Marketing for the Rest of Business 35:15 Are the Models Asymptoting? 39:01 Quiz Pro Quo 44:44 Ageism in Marketing 49:18 Curiosity over Age 58:34 The 100x Marketer 1:03:54 Bulls VS Bears /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/42139680

SPOTLIGHT: Why High Performers Underperform Under Pressure | Kevin Bailey, Co-Founder & CEO @ Dreamfuel 07/17/2026

SPOTLIGHT: Why High Performers Underperform Under Pressure | Kevin Bailey, Co-Founder & CEO @ Dreamfuel A CEO walks into a board meeting knowing exactly what to say then freezes. A sales rep doomscrolls between calls and shows up to the next one flat. A founder grinds toward the exit, only to sacrifice their relationships and themselves along the way. The problem isn't always strategy, skill, or effort. Sometimes, it's the nervous system. Kevin Bailey knows this firsthand. After building a high-growth tech company with around 100 employees, he noticed something strange: some days he was exceptionally creative and productive. Other days, he'd stare at his computer for hours and accomplish almost nothing. That experience eventually led him to earn a master's in applied neuroscience from King's College London and co-found Dream Fuel, a mental performance coaching company helping founders, executives, and sales teams perform at their best under pressure. Sam Jacobs sits down with Kevin to unpack the neuroscience of peak performance and why the mental skills used by professional athletes, fighter pilots, and special forces operators may be just as critical for CEOs and revenue leaders. What we get into: Why founders and executives need mental performance coaching not just executive coaching or therapy The four nervous system states that shape how you perform under pressure Why a freeze response can lower your IQ and leave you struggling for words How doomscrolling between calls can hurt your performance on the next one The neuroscience behind breathwork and nervous system regulation Why presence and awareness are the foundations of peak performance How to move from fight, flight, or freeze back to a state of centeredness Why grinding doesn't have to come at the expense of your relationships or your life The mental performance advantage professional athletes have understood for years How to reach the end of the founder journey with both the outcomeand yourself intact Chapters: 00:00 Intro 00:34 Meet Kevin Bailey and Dream Fuel 01:44 From tech founder to mental performance coaching 04:19 Why mental performance matters more in the age of AI 05:57 Why CEOs need the kind of coaching elite athletes already have 07:24 Therapy vs. mental performance coaching 09:03 What Michael Jordan can teach us about presence under pressure 11:31 The four nervous system performance zones 12:38 Why executives get stuck in fight, flight, and freeze 13:46 What doomscrolling does to your dopamine and performance 15:07 How to regulate your nervous system 15:30 The neuroscience of breathwork and centeredness 17:08 What changes when you master mental performance 18:55 How to win without sacrificing everything that matters 20:19 Kevin's biggest influences and recommended resources 21:49 Where to find Kevin Bailey and Dream Fuel 22:35 Outro Try Dreamfuel: dreamfuel.com /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/42114740

$300M Operator: “70% Of The Executive Playbook Is Obsolete” | Katie Bullard, Board Member & Strategic Advisor 07/12/2026

$300M Operator: “70% Of The Executive Playbook Is Obsolete” | Katie Bullard, Board Member & Strategic Advisor Katie Bullard helped take DiscoverOrg from $30 million to $300 million in revenue, then served as president of A Cloud Guru and Red Canary through exits to Pluralsight and Zscaler. She joins AJ Bruno and Asad Zaman to break down what actually changes for operators in an AI-first world. From why "AI native" is not a growth strategy, to how to align the CRO, CFO, and product team around a single growth plan. Topics include building for customer value before chasing AI ARR, the move from seat-based to consumption pricing, and why 70% of the old playbook for hiring a great executive is suddenly out of date. Also: a reality check on AI accuracy across multi-step work. Plus, a Bulls and Bears debate on whether $200 a week is the real ceiling on AI's value. Key Takeaways: - AI has to earn its keep in customer value, not exist for its own sake. As Katie put it: "Too many companies, I would say, are focusing on the technology … and not on the customer value." Her fix is to ground every AI investment in the ROI it drives for a customer before worrying about the AI ARR label investors keep asking about. - The profile of a great executive is being rewritten in real time. Katie's warning for anyone with a strong track record: "the classic operator of a $100 million business actually will not be particularly successful in a $100 million business today that is redefining itself." She estimates 70% of the pattern-matching investors and recruiters used to hire CROs, CFOs, and CEOs is now out the window, replaced by a hunt for learning velocity over past wins. - AI's success with code does not automatically transfer to the rest of the org. Asad Zaman, CEO at STA, ran the math: "if you take the best model … against any one step … it has 95% accuracy … if you do a 20-step process … that same model achieves 37% accuracy." His point is that stacking agents to cover that compounding error only works when you spend enough compute to make the task uneconomical. - The AI-native shift is already changing how companies hire and build. AJ Bruno, CEO at QuotaPath, said flatly that "Our engineers aren't writing code at all," noting roughly 90% of the company's code now comes from either Cursor or Claude, and framed AI-enabled services at above 70% margin as QuotaPath's real growth engine for 2027. Connect with the Hosts & Guests: 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: Katie Bullard, Board Member & Strategic Advisor - https://www.linkedin.com/in/katiebullard/ 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: Chapters: 00:00 Introducing Katie Bullard 05:24 The $30M to $300M Playbook 09:58 Operating In The Age Of AI 15:54 Aligning The CRO And CFO 23:26 AI Native Is Not A Strategy 25:35 Value First, Then Pricing 26:51 The AI ARR Valuation Puzzle 41:11 Inside The Red Canary Exit 45:35 Betting On AI-Enabled Services 49:15 Rewriting The Hiring Profile 52:51 The Executive Hiring Reset 58:24 The AI Accuracy Reality Check 1:01:16 Why Humans Still Hold The Pen 1:04:53 Bulls and Bears /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/42045280

What It's Really Like To Scale To $1 Billion | CRO @ Replit, Ghazi Masood 07/05/2026

What It's Really Like To Scale To $1 Billion | CRO @ Replit, Ghazi Masood Ghazi Masood, Chief Revenue Officer at Replit, joins Sam Jacobs and Asad Zaman to break down the company scaled from $2 million towards a North Star of $1 billion in revenue in about two years, with roughly 350 employees and a 75-person go-to-market team. Ghazi gets specific on the operational cadence that replaced the quarterly SaaS playbook, why more than 90% of reps overachieved in H1 and why he believes $2 million per rep still isn't the ceiling, and how Replit built its own CPQ, Clari, and Gainsight equivalents on top of Salesforce. Plus, the shift from inbound to outbound pipeline generation, why AI-native orgs run leaner on entry-level headcount and a Quiz Pro Quo on how AI-native companies are structured. In short: a fantastic episode if you want to see how hyper-growth companies are operating, warts and all. Key Takeaways: - The AI-era operating cadence compresses from quarterly to weekly. As Ghazi Masood, CRO at Replit, put it: "forget monthly. We're literally driving a weekly rhythm to the business," with weekly forecast calls, weekly Gong reviews, and a company-wide Friday all-hands they call weekly wins. - Ghazi argues the SaaS-era rep productivity ceiling is gone. Asked whether $2 million per rep is a lot, he said "I would say no… you can do a lot more," after more than 90% of the team overachieved in H1 and enterprise reps blew past $1.5 million in the first half of the year. - Replit keeps a minimal purchased stack and builds the rest on itself. Ghazi described the tools they buy as "HubSpot, Gong, and Salesforce. And that's kind of it," then added "everything else on top of that is Replit. We built our own CPQ on Replit. We're building our own version of Clari on Replit," plus a homegrown Gainsight-style customer health dashboard. - Scaling the team fast, Ghazi made enablement one of his first hires. As he put it, "the very first hire I made was somebody to run and help me build enablement," and that leader built a two-week bootcamp where reps earn a certification before they get a territory. Connect with the Hosts & Guests: Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: Ghazi Masood, CRO at Replit - https://www.linkedin.com/in/ghazi-masood-09195a2/ 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 Ghazi Masood 02:20 Scaling $2M To $1B In Two Years 03:16 The Weekly Operating Rhythm 08:55 What Replit Actually Is 10:21 Building An Outbound Motion 11:29 The SaaS Replacement Wave 19:04 Competing With Claude And Cursor 22:57 Brand And ICP Discipline 25:57 Betting On Model Breakthroughs 28:10 Quiz Pro Quo 44:54 Hiring And Enablement At Speed 52:34 The $2M Per Rep Question 57:41 CRO Versus VP Of Sales 1:00:52 Bulls VS Bears 1:06:50 The GTM Tech Stack /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/41963770

The Godfather of Modern GTM: This Is How To Measure AI Impact | Mark Roberge, Co-Founder @ Stage 2 Capital 06/28/2026

The Godfather of Modern GTM: This Is How To Measure AI Impact | Mark Roberge, Co-Founder @ Stage 2 Capital Mark Roberge, founding CRO at HubSpot and co-founder of Stage 2 Capital, joins Sam Jacobs and AJ Bruno to tackle the question every board is asking in 2026: how do you actually measure AI's impact on a go-to-market team? They get into the revenue velocity formula, why selling time is the one variable AI can realistically double, and the ICONIQ data showing AI lifts top-of-funnel conversion 11% while barely moving active deal cycles. Plus, a Quiz Pro Quo on Palantir's 137% rule of 40 and Twilio's $5.6 million ARR per employee, a debate on whether the AI-era winner is the first mover or the fast follower, and a bull-versus-bear on whether HubSpot is the most mispriced stock in software at $3.5 billion in ARR. Key Takeaways: - Of the four variables in the revenue velocity formula, selling time is the one AI can realistically double right now. As Mark Roberge put it: "best in class has historically been about 30%. And I see a lot of evidence that today's AI can push that to 60% plus… all you do is go from 30% to 60% selling time, just algebraically you double productivity." - Before measuring AI's impact, stop accepting vague claims that a team is "AI-enabled." Roberge said he got fed up hearing it in board meetings if they can't show measurable impact. - Set realistic expectations on what AI has actually delivered so far. Asked whether any company has jumped from tier B to tier A on AI adoption, Roberge was blunt: "Not on like a 2x, but on a 10% to 20%… I've been disappointed… it's not our portfolio, it's just the entire ecosystem." The step-change, he believes, is still ahead. - In the AI era, the copycat often beats the pioneer. "they all say fast follower wins most of the time," Roberge said of the research he could find, "it's about a third first mover, two-thirds fast follower." Faster product cycles and first movers stuck in what he calls "ACV jail" tilt the odds toward the fast follower. 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/ Guest: Mark Roberge, Co-Founder at Stage 2 Capital - https://www.linkedin.com/in/markroberge/ Topline is more than a YouTube Channel: Subscribe to Topline Newsletter: Subscribe to the Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: Chapters: 00:00 Introducing Mark Roberge 01:33 The Science Of Scaling Book 03:57 Vibe Coding Mark's Frameworks 05:42 NPS, Referrals, And Value 09:33 What Is Product Market Fit? 14:34 Measuring AI In Go-To-Market 19:25 The Revenue Velocity Formula 22:43 Selling Time Can Double Output 24:07 AI Use Cases That Move Metrics 32:56 Has AI Created Tier-A Yet? 42:35 How To Measure Selling Time 47:48 Quiz Pro Quo 54:05 First Mover Vs Fast Follower 1:08:42 Bulls And Bears /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/41850145

The $1M Employee Is Here: Why ClickUp Replaced 22% Of Its Team With AI | Gaurav Agarwal, COO @ ClickUp 06/21/2026

The $1M Employee Is Here: Why ClickUp Replaced 22% Of Its Team With AI | Gaurav Agarwal, COO @ ClickUp Gaurav Agarwal, COO of ClickUp, joins Sam Jacobs, AJ Bruno, and Asad Zaman after ClickUp, a company north of $300 million in ARR, parted ways with 22% of its workforce while rolling out pay packages up to $1 million a year for the individual contributors who stay. Gaurav walks through how a central Foundry team builds the tooling while each function's top performers automate their own jobs, why he wants his org to run like a pirate ship before a naval fleet, and how a two-person marketing team now ships 70 to 100 campaigns a week. Topics include which roles get eaten as AI collapses the org chart, why a great seller will never get the AI leverage a great engineer does, the case for working in public so AI has full context, and the mercenary-versus-missionary tension reshaping GTM talent. Plus, a Quiz Pro Quo on the SpaceX IPO and OpenAI's tender offer, and a Bulls and Bears debate on buying applications from foundation model companies versus the pure application layer. Key Takeaways: - Gaurav's mental model moved from treating AI as a sidekick to treating AI as the worker itself. As Gaurav Agarwal, COO of ClickUp, framed it: "AI will do the job, you like it or not... Humans will build AI to do the job and AI will do the job better than an 80th percentile human. And then our jobs become managers and trainers of AI." - ClickUp is rebuilding its compensation bands around the people who create the most leverage with AI. As Gaurav Agarwal put it: "we want our top employees who are using AI to build digital workers... They should be paid higher," and he is blunt that the payoff is uneven by function: "I don't think sales gets the same leverage out of AI the way engineering does." - Standing up an AI-native org early means choosing chaos before structure. Six months into ClickUp's push, Gaurav Agarwal described it plainly: "what I need right now is I need entropy... let's go be a little bit like a pirate ship... then we will bring in someone who can structure those pirates as a naval fleet." - As AI collapses engineering, product, and design into overlapping roles, Gaurav Agarwal made the case for the multi-spike specialist over the generalist: "I think it's an E-shaped specialist... specialists who have more than 2 or 3 spikes eat up those spikes." His rule for who wins the consolidation: "the one with the best taste and the drive to work and learn and improve eats up adjacent departments." 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 Sales Talent Agency - https://www.linkedin.com/in/azaman1/ Guest: Gaurav Agarwal, COO at ClickUp - https://www.linkedin.com/in/gauravragarwal/ Topline is more than a YouTube Channel: Subscribe to Topline Newsletter: Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: Chapters: 00:00 Introducing Gaurav Agarwal 03:55 ClickUp's 22% AI Layoff 05:30 AI Will Do the Job 07:42 Agentic Workflows at ClickUp 10:43 Pirate Ship or Naval Fleet 15:07 AI's Jagged Edges 17:13 Where Do You Start 24:19 AI Amplifies Talent Gaps 25:50 Should You Record Everything 40:28 Quiz Pro Quo 48:56 Paying for AI Leverage 53:27 Mercenary Versus Missionary 1:01:12 Bulls and Bears 1:09:59 Hiring Salesforce GTM Talent 1:12:25 Collapsing Roles and Specialists /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/41712240

"Dead AI Startups Keep Landing On My Desk!" | CEO @ Clari + Salesloft, Steve Cox 06/14/2026

"Dead AI Startups Keep Landing On My Desk!" | CEO @ Clari + Salesloft, Steve Cox Steve Cox, CEO of Clari + Salesloft, joins Sam Jacobs and Asad Zaman to argue that SaaS is far from dead. Steve took the CEO role in December 2025 to merge two of the biggest brands in go-to-market tech into what he calls the world's first predictive revenue system. Topics include the narrative war pushing investors to bet against SaaS-era companies, his one non-negotiable hiring trait, and how to merge two former rivals without one culture eating the other. Plus, a Quiz Pro Quo on go-to-market headcount across US tech and a Bulls and Bears round to close. Key Takeaways: - The AI-native startup boom is already hitting a retention wall, and Steve is watching it arrive deal by deal. As Steve Cox, CEO of Clari plus Salesloft, put it: "the amount of AI native companies that come across my desk now that... are up for sale, you know, they've run out of funding... they grew to 2, 3, 4 million of ARR pretty quickly and then struggled with retention." His read is that everyone knows AI exists now, so driving real adoption "has become more important than ever." - Steve reframes the AI hype cycle as the next layer of infrastructure the industry will absorb, the way it absorbed cloud and big data. As he points out, "how many of us are gonna be talking about AI 3 years from now, 4 years from now?... when was the last time someone mentioned the cloud or Internet of Things or big data?" He expects AI to "layer into everything that we do," which is why he is embedding it into existing revenue workflows rather than fundamentally rebranding the company around it. - The one non-negotiable trait Steve screens for in every executive hire is low ego, because he believes "high ego kills innovation and kills speed." He pairs that with blunt clarity for a merged workforce, telling his first all-hands "It's okay to not to want to be here," so the people who do not buy into the combined company can find the exit fast instead of dragging it down. - Sam Jacobs, CEO of Pavilion, argues a profitable SaaS business with strong retention should ignore where the market trades today. "In the short term, markets are voting machines. In the long term, markets are weighing machines," he said, adding that if you are profitable with good retention, "your customers are voting for you on behalf of the market." The job, in his framing, is to be right long enough that you never have to tap the capital markets at the wrong moment. Connect with the Hosts & Guests: Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: Asad Zaman, CEO at Sales Talent Agency - https://www.linkedin.com/in/azaman1/ Guest: Steve Cox, CEO at Clari + Salesloft - https://www.linkedin.com/in/steve-cox-588a2024/ 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 Steve Cox 02:07 From Bananas to Enterprise Tech 03:05 Can SaaS Beat AI Startups? 04:33 AI Hype and the 95% Problem 06:57 The CEO Integration Playbook 10:27 Hiring for Low Ego 15:30 AI Startups Landing on His Desk 21:10 The SaaS vs AI Narrative War 26:23 Is Patience a Moat? 33:43 The Predictive Revenue System 38:21 Quiz Pro Quo 44:10 Merging Two Rivals 49:40 Culture After a Merger 59:03 Founder Mode vs Operators 1:02:48 Bulls and Bears /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/41635420

$100M+ Profit. Stock Down 72%. CEO Explains Why | Michael Walrath, Chairman & CEO @ Yext 06/07/2026

$100M+ Profit. Stock Down 72%. CEO Explains Why | Michael Walrath, Chairman & CEO @ Yext Michael Walrath, Chairman and CEO of Yext, returns to break down why the market has left a profitable, $400 million mid-cap public software company trading at one times revenue, even with over $100 million in EBITDA. He joins AJ Bruno and Asad Zaman to argue that the so-called SaaS apocalypse has almost no data behind it, that most AI layoffs are really a decade of go-to-market overhiring unwinding, and that boring compounders still out-return the hypergrowth darlings. Topics include how venture capital distorts software valuations, why no one is coming to help the 2021 unicorns stuck in broken cap tables, the great GTM despecialization, and the extend-and-pretend game inside venture funds. Plus, a Quiz Pro Quo on new business creation in the US and a Bulls and Bears debate on the future of mid-cap software and the stickiness of the AI platform. Read Michael's essay, No One's Coming to Help You: https://x.com/michaelpwalrath/status/2051364181237010778 Key Takeaways: - The market has left profitable mid-cap software for dead in favor of AI-native growth stories, and Michael Walrath, Chairman and CEO at Yext, leaned into how strange that is for a business that still prints cash. As he put it, "who's writing our obituary? It's the venture capitalists who are funding high-growth ARR companies," even as those same firms can't say what that ARR really means. - The loudest voices setting software valuations are venture investors, and Michael argued their certainty is out of step with their actual hit rate. He called them "remarkably sure of themselves for guys whose whole business model is being right 5 to 10% of the time," noting that being right much more often than that would mean a VC is playing it too safe. - Michael's answer to the hypergrowth-or-die mindset is that durable value comes from compounding cash flow, not chasing the next high-growth story. Pointing to a century of market history and operators like Berkshire Hathaway and Liberty Media, he said, "if you compound effectively, you will out-return these super high growth stories, unless those super high growth stories eventually become compounders." - A lot of the layoffs being blamed on AI may be a decade of go-to-market overhiring finally unwinding. Michael framed the skeptic's question directly: "is it really AI? Or is this a choice that you're making because you overhired for 10 years." Asad Zaman, CEO at Sales Talent Agency, agreed, pointing out that even inside the most AI-native companies he visits, the fundamental way the business runs has not really changed. Connect with the Hosts & Guests: Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at Sales Talent Agency - https://www.linkedin.com/in/azaman1/ Guest: Michael Walrath, Chairman & CEO at Yext - https://www.linkedin.com/in/michael-walrath-b63166/ 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 Cold Open and Intro 02:33 Dead But We Just Don't Know It 08:47 Narrative Violations and Hype 11:00 VCs Right 10% Of The Time 14:22 Whose Case Are You Making? 19:20 Why Boring Compounders Win 24:55 The SaaS Apocalypse Myth 28:47 Are AI Layoffs Really AI? 36:16 The Great GTM Despecialization 39:55 Quiz Pro Quo 48:54 No One Is Coming To Help You 55:11 Extend And Pretend 1:01:41 Doubling Cash Flow In 5 Years 1:04:17 Bulls and Bears 1:07:30 What's The AI Moat? /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/41560425

Build The World Class Team That Anthropic Won’t Steal | Craig Rosenberg, CPO @Scale Venture Partners 05/31/2026

Build The World Class Team That Anthropic Won’t Steal | Craig Rosenberg, CPO @Scale Venture Partners Craig Rosenberg, Chief Platform Officer at Scale Venture Partners and co-founder of Topo, joins AJ Bruno and Asad Zaman to take on the question every founder is wrestling with: can you still build a world-class sales team when OpenAI and Anthropic are handing individual contributors $10 million equity packages? Craig argues you do not have to compete head-on, then lays out the hiring profile to chase instead, the quota-to-comp discipline that keeps packages sane, and why founder brand has become the most reliable pipeline play left as CAC keeps climbing. Topics include enterprise AE compensation, where private equity is still winning the GTM talent war, the Topo playbook for events and data-as-moat, and a bull-versus-bear debate on whether Gong goes public in the next 36 months. Plus, a Quiz Pro Quo on the real customer counts behind Salesforce, HubSpot, and ZoomInfo. Key Takeaways: - Rather than try to outbid OpenAI and Anthropic for talent, build your own farm system and develop people into the role. As Craig Rosenberg, Chief Platform Officer at Scale Venture Partners, put it: "You have to change your hiring profile to a unique profile that's unique to your business, but then you gotta coach 'em up." - A resume from a hot AI lab is not a guarantee of success at your company. As Craig Rosenberg noted, "The person that is going to do well at Anthropic may not do well at Series B," so hire for the stage and the hunger rather than the logo. - On compensation, Craig anchors the package to the role's real value: "you pay for what your wedge costs… if you feel like you have to pay $10 million, then you have a huge problem and you gotta go back to the drawing board." If the number runs away from you, the model is broken. - With CAC climbing and most channels breaking down, founder brand has become the highest-leverage pipeline play. As Craig Rosenberg said, "The value of building a founder brand, when you look at the data, it's amazing," pointing to gains in both pipeline and deal size. Connect with the Hosts & Guests: Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at Sales Talent Agency - https://www.linkedin.com/in/azaman1/ Guest: Craig Rosenberg, Chief Platform Officer at Scale Venture Partners - https://www.linkedin.com/in/craigrosenberg/ 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 Craig Rosenberg 02:34 Can Anyone Out-Hire The AI Labs? 04:33 Why Craig Isn't Worried 06:52 Enterprise AE Comp Is Climbing 08:21 Founders Overpay For Star CROs 10:53 Why AI Reps Struggle At Series B 14:00 Hire The Slighted CRO 14:42 Quota-To-Comp And Attainment 18:45 Can AI Labs Sustain Growth? 22:20 Where PE Still Wins GTM Talent 27:17 Major Runs Reshape GTM 32:36 The Topo GTM Playbook 37:55 Quiz Pro Quo 47:45 Founder Brand And Rising CAC 58:42 Bulls and Bears /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/41479685

AI Marketing Has A Disease. Can The Cure Be Bought, Taught, or Caught? | Kyle Lacy, CMO @ Docebo 05/24/2026

AI Marketing Has A Disease. Can The Cure Be Bought, Taught, or Caught? | Kyle Lacy, CMO @ Docebo Kyle Lacy, CMO at Docebo (previously Lessonly, Seismic, Jellyfish), joins Sam Jacobs, AJ Bruno, and Asad Zaman to push back on AI-era “efficiency” gospel in marketing. Topics include why product marketing under a sales-led organization will die, and the one-page Wall Street Journal manifesto every CMO should make their CEO write. Plus, why OpenAI and Anthropic might be lost when it comes to POV...AND the $300M Windows 95 launch with Jennifer Aniston and a Polish submarine (obviously). Key Takeaways: - Build the company manifesto first. As Kyle Lacy, CMO at Docebo, framed it: “I frame it with my CEO as... you have a direction you want to take this company. I need a one-page document that reads like a manifesto that you would publish in the Wall Street Journal tomorrow as a full-page ad. And that's our guiding light.” Messaging pillars, ICPs, and personas all flow from that single document; the framework can never be the source. - Spend 80% on demand, then defend the other 20% for brand. Kyle's decade-long rule: “If you can figure out how to generate the demand you need off of 70 to 80% of your budget, then you can do whatever the hell you want, like golden llamas or hiring Jennifer Aniston to do your software training, whatever.” Marketing leaders who haven't earned pipeline credibility lose the brand line item first when budget tightens. - Don't fold marketing under the CRO. “Product marketing living under a sales-led organization, it will die, will die slowly because you can't get the right people in the role that want to do it,” Kyle said. He distinguishes between marketers becoming CROs (good) and marketing being absorbed structurally into the revenue org (fatal) because the executive-level tension between brand and demand is what protects both. - The Lessonly playbook wouldn't survive 2026. Kyle's honest reading: “Lessonly in this age would get eaten alive. Our software did not have a moat. It was really simple to use. You could probably vibe code it down a weekend.” What does survive is the customer-first culture and the storytelling. At Docebo's recent Inspire user conference in Miami, customers organically produced more LinkedIn content about the event than the team had ever seen, with zero solicitation campaigns. 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 Sales Talent Agency - https://www.linkedin.com/in/azaman1/ Guest: Kyle Lacy, CMO at Docebo - https://www.linkedin.com/in/kylelacy/ 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: Chapters: 00:00 Introducing Kyle Lacy 03:30 Is Brand Building Having Its Moment? 08:33 Word Is Brand: The 60/40 Mix 11:12 Surprise and Delight, Lessonly Lore 16:36 The Manifesto Framework 19:37 OpenAI and Anthropic Have No Manifesto 26:40 Brand at the Application Layer 27:35 Six Figures, No Anthropic Time 32:35 Quiz Pro Quo 39:27 SaaS-Era Marketers Under Attack 43:10 Should Marketing Report to a CRO? 54:42 Authenticity, Jellyfish, and Docebo 57:06 Bulls and Bears /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/41405310

Playbook: AI-Era Customer Success For Hyper Growth | Sam Slevin, Global SVP CS @ AlphaSense 05/17/2026

Playbook: AI-Era Customer Success For Hyper Growth | Sam Slevin, Global SVP CS @ AlphaSense Sam Slevin, Global SVP of Customer Success at AlphaSense, joins Sam Jacobs, AJ Bruno, and Asad Zaman on the AI-era customer success playbook. Topics include why service is the differentiator over the next 2 to 3 years, the case for customer success owning a revenue number from day one, the gap between finance's productivity targets and real-life capacity. Plus, the origins of customer success, why consumption-based pricing can quickly become a trap, and a bull-versus-bear debate on whether HubSpot can get back to a $20 billion market cap. In short... big episode! Key Takeaways: - After 17 years building customer success teams, Sam Slevin doesn't entertain the "should CS own a number" debate. As Sam Slevin, Global SVP of Customer Success at AlphaSense, put it: "in my 17 years of, of customer success and leadership within customer success, that has never actually been a debate for, for me. I, I would never take a role that doesn't have revenue focused and like impact owning a number, calling your forecast from day one." His standing practice when he joins a new company: build a top-down and bottoms-up forecast on day one and validate it the same way sales does. - Slevin's central thesis is that AI raises the floor on automation while service becomes the upside lever for the next 2 to 3 years. As Slevin put it: "I don't think there could be a more exciting time to be in customer success where service feels like it could be the major differentiator over the next 2 to 3 years." The CS team that listens carefully, builds deep relationships, and meets customers where they are wins the renewal and the expansion. - The hardest tension in CS productivity is the gap between what finance models demand and what individual accounts actually support. As Slevin put it on his approach: "I definitely want to increase productivity in ARR per AM. What's interesting is I feel like there's a finance model and then there's a real life model… finance will say we need $15 million per AM." The leader's job, Slevin argues, is to find the 10% operational drag (AM-to-AE handoffs, billing friction, segmentation gaps) and remove it to close the gap. - On HubSpot's path back to $20 billion, AJ Bruno takes the bullish side based on customer behavior signals. As AJ Bruno, CEO at QuotaPath, put it: "And the fact that they've gone horizontal, um, now I know that there are like 70% of their customers are still looking for answers for HubSpot of what AI needs to look like, and they haven't let the opportunity yet pass them by, but it's getting shaky right now." Sam Jacobs took the bearish side, citing structural challenges and faster-moving AI-first competitors. 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 Sales Talent Agency - https://www.linkedin.com/in/azaman1/ Guest: Sam Slevin, Global SVP Customer Success at AlphaSense - https://www.linkedin.com/in/sam-slevin-9b2ba21b/ 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 Sam Slevin 03:13 Customer Success in the AI Era 04:28 Should CS Own a Number? 07:43 Gross Retention vs. Growth 11:02 The Number-Owner Premium 14:37 Service as the AI-Era Moat 22:19 Productivity Per Person 26:34 Vendor Spend and AI Voice Modes 35:12 Reimagining GTM Roles 38:51 Quiz Pro Quo 45:38 Seat to Usage-Based Pricing 50:12 Pricing AI Like a Meter 55:43 CSM vs Salesperson Comp Gap 58:43 Bulls and Bears /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/41319580

AI Cyber Exec: Vibecoding Is A Security Time Bomb | Ryan Burke, VP Worldwide Sales @ Crogl 05/10/2026

AI Cyber Exec: Vibecoding Is A Security Time Bomb | Ryan Burke, VP Worldwide Sales @ Crogl Ryan Burke, VP of Worldwide Sales at Crogl, joins Sam Jacobs, AJ Bruno, and Asad Zaman on the new economics of enterprise cyber risk. Topics include Anthropic's Mythos model, AI for the security operations center, why vibe-coded apps are far more likely to have security issues, why Claude Design tanked Figma's stock, and what the Elon Musk versus OpenAI lawsuit signals for AI governance. Key takeaways: AI has crashed the cost of running sophisticated attacks, putting nation-state-grade tooling in the hands of low-skill operators. As Ryan Burke, VP of Worldwide Sales at Crogl, put it on Anthropic's Mythos model: "Mythos has lowered the cost to like the dollar menu equivalent of...running an attack...so more people can do it." Enterprises are staring down a multi-year patching backlog that runs from now until the end of time. Non-technical teams in finance, ops, and HR are shipping internal tools using Replit and Claude, and almost none of them are securing what they build. Ryan Burke flagged the research: "vibe-coded software is almost 3 times as likely to have security issues." When the employee who built the agent quits, the agent stays behind with no owner, no documentation, and quiet access to systems it never should have had in the first place. For founders eyeing an exit, security has joined revenue, IP, and hitting your numbers as a non-negotiable diligence pillar. As Ryan Burke explained: "lack of security can kill an acquisition...a fourth pillar now is you're secure." Acquirers like JPMorgan Chase will not buy a fintech startup that turns into a vector for attackers to walk straight into their environment. The market case for NRR-fortress legacy SaaS may be weaker than the last decade made it look. As Asad Zaman, CEO of Sales Talent Agency, argued: "there was a generation of software companies that had signs that they had really good customer relationships...but their customers felt more like prisoners." If AI makes switching cheap and a new generation of software actually delights users, the moats around system-of-record incumbents start to compress fast. Connect with the hosts and guest: 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 Sales Talent Agency - https://www.linkedin.com/in/azaman1/ Guest: Ryan Burke, VP Worldwide Sales at Crogl - https://www.linkedin.com/in/ryan-burke-bos/ 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 Ryan Burke 03:14 Anthropic Mythos and Cyber Risk 04:20 How Attackers Use AI at Scale 07:00 Dollar Menu Attacks Explained 10:41 AI for the Security Ops Center 14:53 Why Claude Tanks Figma's Stock 18:30 Sam's Advice on Falling Stocks 20:50 Are Legacy SaaS Companies Back? 24:04 The Vibe-Coding Risk Surface 27:56 Quiz Pro: Cybersecurity Edition 33:46 Replit Apps Inside Enterprises 40:18 Security as the M&A Fourth Pillar 44:17 Personal Data and Digital Legacy 47:24 Bulls vs Bears: Elon vs OpenAI 52:03 Will ServiceNow Hit $32B? /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/41236255

Top Investor: AI Killed Most Moats. These 4 Still Work | Liz Christo, Partner @ Stage 2 Capital 05/03/2026

Top Investor: AI Killed Most Moats. These 4 Still Work | Liz Christo, Partner @ Stage 2 Capital Stage 2 Capital General Partner Liz Christo joins the show to discuss the disconnect between venture expectations and reality in the software market. The conversation covers the hidden costs of the new build versus buy debate, the structural changes happening within modern sales organizations, and whether traditional B2B SaaS go-to-market strategies and moats still matter when AI coding tools make software replication cheaper than ever. Key Takeaways: -The shift toward building internal AI tools instead of buying SaaS products overlooks long-term technical debt, as Liz Christo points out that "there's like a huge amount of cost buried behind the scenes that we're not really talking about today because it's still like sexy and fun." -Founders are artificially inflating their Total Addressable Market to meet new venture capital baseline expectations, with Liz Christo noting that "pitch decks read like really ridiculous right now where everybody wants to tell the story of like a $10 billion outcome because that's the new milestone that got set." -Revenue Operations is becoming the most direct path to the Chief Revenue Officer seat in AI-first organizations, which Sam Jacobs explains is "because as we use fewer humans and more agents, the sort of the half technical, the semi-technical capabilities of most RevOps people will translate into orchestrating armies of agents." -Delegating analysis and writing to AI risks destroying strategic judgment across go-to-market teams, a trend Liz Christo summarizes by stating, "I think we are producing an incredible amount of content that's not getting consumed... I just think we're like losing the ability to think and we're not teaching junior employees how to do it." Connect with the Hosts & Guests: Host: Sam Jacobs - Host: AJ Bruno - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman - https://www.linkedin.com/in/azaman1/ Guest: Liz Christo - https://www.linkedin.com/in/lizchristo/ 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: Chapters: 00:00 Intro and Cold Open 02:41 The New Build vs Buy Debate 06:10 Engineers in Every Department 10:48 Pitch Decks and 10B Dollar TAMs 17:53 Venture Capital Funding Quiz 23:43 AI Memos and Critical Thinking 42:41 Software Moats and Switching Costs 47:46 Bulls vs Bears Segment 48:23 RevOps as a Path to CRO 51:25 The Future of SDR Managers 55:14 Is Clay Actually Undervalued 59:12 Odds of Hitting 50M ARR /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/41129120

VC Whisperer: There Will Be No Exits For... | Peter Walker, Head of Insights @ Carta 04/26/2026

VC Whisperer: There Will Be No Exits For... | Peter Walker, Head of Insights @ Carta Peter Walker brings Carta's proprietary private market data from 60,000 startups and 85% of US unicorns to expose the brutal realities of today's tech landscape. While Q1 saw record capital raised, the money is highly concentrated among foundation models. We review the harsh truth behind the 530,000 open tech jobs in the US and the widening talent divide separating top 10% performers from the rest of the market. The conversation covers why venture capital is squeezing operators, how private equity is no longer a guaranteed exit strategy, and the urgent need to optimize your GTM strategy for AI-native workflows. We also debate the death of long-term product roadmaps, the impact of AI on enterprise pipeline generation, and evaluate whether middle management will survive the next 24 months. Key Takeaways The traditional safety net for slow-growth SaaS companies has disappeared, with Peter Walker noting that "A lot of companies held out this PE route as like, this is my escape hatch if I don't grow that fast. And now they're finding it's like, actually, the PEs don't care about you either." Securing venture capital has never been harder for founders outside of the AI bubble, as Peter Walker states "it's definitely not the easiest time to raise money unless you are already in the legible cohort. And if you're in the legible cohort, you know who you are." Rapid execution is replacing traditional product planning, with Peter Walker emphasizing that "the companies that are moving fast… don't know what they're doing in three weeks... we have no idea what's going to happen in October." Artificial intelligence is fundamentally threatening traditional communication hierarchies, and Sam Jacobs is bearish on the future of people managers because "if the purpose of management is to facilitate decision making at certain executive levels, that is something that AI can do." Connect with the Hosts & Guests Host: Sam Jacobs - Host: AJ Bruno - Host: Asad Zaman - Guest: Peter Walker - 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: Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: Chapters: 00:00 The AI Funding Divide 02:36 Is It Harder to Raise Capital 04:37 VCs Only Care About Growth 06:44 The Death of the PE Exit 10:48 Transitioning to AI Native 14:50 Why Product Roadmaps Are (Kinda) Dead 19:19 Stop Defaulting to VC 29:11 Historic Tech Funding Rounds 31:59 Over 530K Open Tech Jobs 36:55 Hiring Market Concentration 46:29 The Growing Tech Talent Divide 49:11 VC Fund Performance Realities 54:28 Future of Foundation Models 58:29 The End of Middle Management /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/41016040

The #1 GTM Engineer In The World | Jordan Crawford, Founder @ Blueprint GTM 04/19/2026

The #1 GTM Engineer In The World | Jordan Crawford, Founder @ Blueprint GTM In this episode, Jordan Crawford outlines how revenue leaders can build an autonomous pipeline generation engine and transition away from static playbooks. The discussion covers practical methods for extracting competitor usage data, identifying segments of users who are far more likely to buy, and generally how top GTM teams are using GTM Engineering to dramatically improve their results. The hosts also evaluate how AI tools alter revenue operations, shift the traditional B2B SaaS go-to-market strategy, and force a total redesign of traditional AE compensation models. Key Takeaways: Top-down executive mandates fail because leadership lacks hands-on experience with the required technical systems. Jordan Crawford notes the absurdity of this disconnect, stating, "You read these letters from all these CEOs and they're like, 'We need to be an AI first organization and I can't tell you what that means or how to implement it, but goddamn, you need to be able to do it.'" The core function of revenue operations must shift from administrative reporting tasks to running active market tests. Sam Jacobs explains this organizational friction, observing many Rev Ops employees think their job is still to deliver reports to the C-Suite and ensure data accuracy, when today’s reality is that “actually your job now is to generate demand and like I need 50 campaigns tested by tomorrow." Identifying high-value target accounts requires prioritizing product telemetry and user actions over static CRM fields. Jordan highlights the power of this approach, explaining that "AI can basically analyze customers' words, actions, and what's in the CRM and say... these accounts are worth 10 times more than these accounts." Connect with the Hosts & Guests: Host: Sam Jacobs - Host: AJ Bruno - Host: Asad Zaman - Guest: Jordan Crawford - Topline is more than a YouTube Channel: Subscribe to Topline Newsletter: Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: J Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: Chapters: 00:00 Podcast Episode Introduction 02:52 Reversing GTM Strategy 06:44 RevOps and AI Thought Partners 13:58 Executing Fast Sales Campaigns 18:25 AI For Comp Plan Benchmarks 21:04 Defining Pain Qualified Segments 26:42 Shifting RevOps Priorities 38:41 Unbundling B2B SaaS Jobs 39:21 The Topline Trivia Game 45:11 Top Of Funnel AI Tactics 46:43 Middle Of Funnel Telemetry 47:56 Bottom Of Funnel Contract Review 49:10 Bull/Bear Predictions /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/40922840

How Top VCs Pick Winners In 2026 | Cassie Young, General Partner @ Primary Venture Partners 04/12/2026

How Top VCs Pick Winners In 2026 | Cassie Young, General Partner @ Primary Venture Partners Cassie Young, Partner at Primary Venture Partners, joins the show to break down their contrarian $625 million seed fund and the reality of the coming gross retention apocalypse for tech companies. The conversation outlines why classical venture logic is breaking and how AI-native CRMs are plotting to steal enterprise market share from legacy giants like Salesforce. The group also details why the $6 trillion white-collar labor pool is the real target for emerging AI workflows rather than traditional software budgets. Expect a direct discussion on the myth of the zero CAC CEO, the evolving definition of the jaw-dropping customer experience, and the specific signals Primary looks for when writing checks to early-stage go-to-market founders building the next wave of B2B SaaS products. Key Takeaways -Primary Ventures just raised a massive $625 million seed fund by challenging traditional venture capital models, as Cassie explains, "The conventional wisdom at seed is to stay small. We fundamentally disagree with that." But don’t worry: Cassie explains why they believe their approach is the right one. -Cassie warns that a retention reckoning is inevitable for AI startups noting, "I still very much live in fear of this... it might not be next month, it might not be next year, but it's ultimately going to come." Meanwhile, the hosts wonder: is it truly inevitable? Or just highly likely? -Cassie points out that a "Zero CAC CEO who's not supplemented by amazing technologists, it's just not enough." And that’s just one of the many classic competitive moats which Cassie flags as reducing in value. -Asad highlights how rapid AI advancements are forcing companies to continuously rethink their competitive moats and sales motions, stating, "There are no product advantages that are long-lasting anymore." Connect with the Hosts & Guests Host: Sam Jacobs - Host: AJ Bruno - Host: Asad Zaman - Guest: Cassie Young - Topline is more than a YouTube Channel: Subscribe to Topline Newsletter: Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: Chapters: 00:00 Cassie Young Joins Topline 04:37 Raising a $625M Seed Fund 08:08 How Primary Wins Seed Deals 12:56 The 6 Trillion AI Opportunity 19:04 Can AI CRMs Beat Salesforce 29:14 Gross Retention Apocalypse 40:12 Myth of the Zero CAC CEO 46:58 Eradicating Switching Costs 53:15 Backing Go-to-Market Founders /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/40814240

What World-Class AI in GTM Looks Like | Kyle Norton, CRO @ Owner.com 04/05/2026

What World-Class AI in GTM Looks Like | Kyle Norton, CRO @ Owner.com Kyle Norton’s AI-enabled revenue team at Owner.com has completely rewritten the economics of what’s possible in sales. Kyle joins the show to share why decentralized AI rollouts fail, how to build a core intelligence engine centrally, and why early AI investments must focus on one specific area. The hosts also discuss navigating go-to-market strategy shifts, rethinking RevOps AI integration, and why sales leadership can no longer use budget constraints to delay AI adoption. Key Takeaways: -Building a highly functional AI go-to-market strategy requires a perfect mapping of your entire market and deep enrichment, as Kyle Norton notes to "start with data... without that, nothing really works because you can't give the models what they need to make smart decisions or give you good outputs." -Pushing individual reps to build their own AI workflows yields poor results compared to building central intelligence, which is why Kyle Norton realized that "all of the best things, all of the most impactful implementations were all highly centralized... you just get a completely different result out of it and you can properly enable your whole org to adopt it." -Companies looking to see immediate ROI from their AI investments need to direct their resources toward the top of the funnel, with Kyle Norton emphasizing that "80% of your AI efforts in your early innings should be pipeline focused... AI is a really good pipeline tool." Connect with the Hosts & Guests: Host: Sam Jacobs - Host: AJ Bruno - Host: Asad Zaman - Guest: Kyle Norton - Topline is more than a YouTube Channel: Subscribe to Topline Newsletter: Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: Chapters: 00:00 - Introduction 04:05 - Data Foundations for Sales AI 08:14 - Predicting Lead Connect Rates 10:05 - Centralized AI Rollout Strategy 17:20 - Building the Intelligence Engine 22:05 - AI Investments for Startups 28:12 - Changing Comp Plans Quarterly 33:58 - Centralizing AI by Department 37:35 - The Five Ps Decision Framework 39:33 - Focusing AI on Pipeline Gen 43:16 - Salesforce Acquisition Strategy 45:24 - The Reality of Founder Mode 48:01 - The Next Phase of AI Workflows /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/40734545

Is This The End of Sales As We Know It? (CEO @ 1mind, Amanda Kahlow) 03/29/2026

Is This The End of Sales As We Know It? (CEO @ 1mind, Amanda Kahlow) Amanda Kahlow raised $30 million to build AI sales agents that improve the buying experience. As the founder of 1mind and previously 6sense, she sits at the forefront of modern go to market strategy. In this episode, Sam Jacobs, AJ Bruno, and Asad Zaman sit down with Amanda to discuss the reality of AI in the sales motion; she explains how Superhumans (1mind’s AI Agents) handle everything from top of funnel enterprise pipeline generation to acting as sales engineers on live demos. The conversation covers the technical hurdles of building high performing AI agents, why she believes buyers will soon demand to interact with AI over human sellers, and what revenue leaders must do to prepare their teams for a radically different future. Key Takeaways: According to Amanda, the speed and accuracy of application specific AI will soon eclipse traditional human selling, as Amanda Kahlow predicts that "When buyers realize their answer is going to be more accurate and more empathetic, they're going to demand to talk to an AI over a human." The traditional role of the sales representative is facing total disruption, and Amanda Kahlow states clearly that in the future "I don't think there will be sellers... I think the best thing we can do for sellers and for the market right now is to be f***ing honest about what is coming for them." Product development for revenue technology must prioritize the end customer over internal efficiency, a philosophy Amanda Kahlow emphasizes by noting that "If I can create a better buying experience, I believe the rest will fall into place... if that's not a better buying experience, I want to be a hard no to it." Connect with the Hosts & Guests: Host: Sam Jacobs - Host: AJ Bruno - Host: Asad Zaman - Guest: Amanda Kahlow - Topline is more than a Podcast: Subscribe to Topline Newsletter: Tune into Topline on YouTube, the #1 podcast for founders, operators, and investors in B2B tech: Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: Chapters (Audio Version): 01:00 Introducing Amanda Kahlow and 1mind 02:27 What are Go To Market Superhumans? 06:50 Managing AI Latency and Models 09:53 AI: More Trustworthy Than Human Sellers 15:40 Building the Future of GTM Tech 22:25 The Next Three Years of GTM 35:16 Closing Six Figure Enterprise Deals 40:01 Will Sales Reps Exist in Two Years? 50:00 Collapsing the Sales Assembly Line 54:08 Adapting to the AI Sales Era 58:36 The Autonomous Context Graph Future /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/40654830

Why Intercom Destroyed Its Predictable SaaS Revenue 03/22/2026

Why Intercom Destroyed Its Predictable SaaS Revenue Intercom gave up $60 million in contracted seat-based ARR to bet the entire company on an AI agent named Fin. The result? They passed $400 million in total ARR, with Fin driving over $100 million in revenue and 35% growth. In this episode, Sam Jacobs, AJ Bruno, and Asad Zaman break down what went into this massive turnaround. The conversation starts with the problem: the SaaS market cap dropping by $600 billion, and how this creates an urgent need for structural pivots. The hosts discuss the financial reality of agentic business models, why historic 90% SaaS gross margins are disappearing, and how scaling compute costs will impact your GTM strategy. The episode wraps up with tactical advice on managing board support, handling leadership pushback, and executing a burn-the-boats transition before your legacy product-market fit evaporates. Link to Intercom CEO Eoghan McCabe’s essay: Key Episode Takeaways: - Shifting to an AI-first product fundamentally changes your financial model, requiring exponential revenue generation to offset massive compute costs, which Sam Jacobs points out by stating, "You are trading a good business for a worse business... you have to grow at exponential rates as an agentic business because your gross margins are so much lower than SaaS." - Comfort is the enemy of innovation for established software companies, and survival often requires a massive operational reset, as AJ Bruno explains when noting that "Intercom had five straight quarters of zero net new ARR growth” before they took drastic action. - The cost of human capital is rising as top performers require heavy compute access to execute their roles effectively, a reality Asad Zaman highlights by predicting that "Every recruiter at STA will probably have $10K, $20K, $30K worth of inference calls in the next couple of years... That's like a mini assistant for each person." Connect with the Hosts: Host: Sam Jacobs - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman - Topline is more than a YouTube Channel: -Subscribe to Topline Newsletter: https://www.joinpavilion.com/topline-newsletter -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 Intro and Episode Overview 01:21 Intercom 400M ARR Turnaround 03:41 The Massive SaaS Market Cap Reset 05:27 Executing a Burn the Boats Pivot 09:05 Gross Margins of AI vs Legacy SaaS 12:00 Defending App Commoditization 18:16 Returning to Founder Mode 27:29 Why You Need Full Board Support 32:26 The Danger of Comfortable Growth 36:31 The Real Cost of AI Inference 42:27 Rising Talent Compute Economics 49:25 Tracking the Right Churn Metrics 52:38 Shifting GTM to Vertical SaaS /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/40569830

Do SaaS Teams ACTUALLY Need AI? 03/15/2026

Do SaaS Teams ACTUALLY Need AI? Sam Jacobs (CEO, Pavilion), AJ Bruno (CEO, QuotaPath), and Asad Zaman (CEO, Sales Talent Agency) debate exactly how to handle team members resisting AI adoption. When to leave them, when to nudge them, and when to fire them. The discussion highlights real-world data, including how leading companies reach the top decile of AI adoption and the mechanics of running a 24-hour, four-squad AI hackathon to force experimentation. We also cover a critical performance heuristic from the past CPO of LaunchDarkly: if your team cannot execute simple tasks in a single day, you are falling behind. The conversation covers change management for revenue leaders, how to integrate AI into your daily enterprise pipeline generation, and why optimizing your GTM strategy means making hard decisions about personnel who refuse to adapt. Key Takeaways: >Driving AI adoption requires clear communication and rewarding good behavior, but AJ Bruno warns that leaders will ultimately have to "leave behind a handful of folks that are just not going to get on the bus, that aren't getting on board." >When implementing new AI tools across your teams, Asad Zaman notes that expectations must scale with seniority, stating "I have more tolerance as I move lower in the org and less tolerance at the higher levels." >AI should be treated as a creative partner for deeper analysis rather than a shortcut for unedited output, a reality Sam Jacobs emphasizes by warning "If you are just the pass through, you will be fired." Connect with the Hosts Host: Sam Jacobs - Host: AJ Bruno - Host: Asad Zaman - Topline is more than a YouTube Channel: Subscribe to Topline Newsletter: Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: Chapters: 00:00 Intro 00:35 The Question: Employees resisting AI 01:39 Convert them or fire them? 02:07 Running internal AI hackathons 03:54 How CEOs drive adoption 05:08 Mapping tasks to AI agents 06:27 The “Robot Layer” in emails 07:40 Claire Vo’s anti-dinosaur framework 08:07 The One-Day Execution Heuristic 12:52 Why you should be scared 14:30 Elevating junior AI talent 16:35 Reducing 3 hours of work to 45 mins 18:54 Summary: How to uplevel the org 21:09 The tension between speed and depth 21:52 Pass-through? Fired! FIRED!!! /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/40320325

This is How Tech Executives Will Get Hired in 2026 03/08/2026

This is How Tech Executives Will Get Hired in 2026 Is your traditional SaaS experience becoming obsolete? In this new 20-minute rapid-fire format, Sam Jacobs, AJ Bruno, and Asad Zaman tackle a specific listener question: How does a senior operator transition from a legacy B2B SaaS role into a high-growth AI company? The market is shifting toward a meritocracy where recent hands-on capability outweighs decades of tenure on a CV. The hosts break down exactly how to position yourself for companies like CoreWeave and EliseAI. They discuss why hiding your lack of technical engineering skills is a mistake, how to build a portfolio of "work product" using low-code tools like Replit and Claude, and why being able to articulate the failures of AI models is actually the strongest signal of fluency. Key Takeaways: - Stop relying on a static resume and start building a portfolio of practical applications. As Sam Jacobs notes, the hiring landscape has shifted so that "your work product needs to speak for itself... demonstrating that you're capable of working with these tools, not theoretically, but practically through your conversations that you're having with hiring managers." - We are entering a career reset where agility beats seniority. Asad Zaman warns that "whenever there is a platform shift... the value of experience goes down a little bit," which creates a massive opportunity for younger leaders to "move up faster if you present in a very compelling manner because people are not looking at titles the same way." - Cultural currency matters as much as technical skill. To be taken seriously by founders in this space, you must consume information where they do. As Asad Zaman puts it, "If they find out that you're not on AI Twitter or AI X, I think they will think you're not a serious person... the information is not gonna be found in these old school channels." Connect with the Hosts: Host: Sam Jacobs - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman - Topline is not JUST a YouTube Channel! Subscribe to Topline Newsletter: Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: 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 Intro 01:58 Viewer Q: Transitioning to AI 02:48 Show Work Product, Not Just CVs 04:36 Applying SaaS Principles to AI 05:58 The AI-First Mentality 08:58 Articulating AI Limitations 11:30 The Meritocracy Shift 13:55 Unexpected AI Wins 21:27 Staying Culturally Relevant 24:29 Summary: How to Get Hired /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/40291450

Citrini Needs to Chill (but SaaS DOES Need to Change) 03/01/2026

Citrini Needs to Chill (but SaaS DOES Need to Change) Citrini Research claims AI agents will replace white-collar jobs by 2028, triggering a massive economic crash (and repricing of SaaS stocks). Sam Jacobs, AJ Bruno, and Asad Zaman analyze the validity of this thesis and the immediate impact on enterprise valuation multiples. The discussion moves to the practical realities of the innovator's dilemma, specifically how legacy software companies must cannibalize their own revenue to survive. They cover strategies for GTM transformation, the loss of pricing power in traditional SaaS, and why Gong's pivot to "Chief Revenue Architect" signals a deeper identity crisis in the market. Key Takeaways: * The hardest part of adapting to AI is destroying your current margins. Sam Jacobs argues that leaders get emotionally attached to ARR, noting that "the hardest part of the innovator's dilemma is price... the only way to get out of it is to... go towards a worse business" in the short term. * Pivoting sounds great on paper, but is far harder in practice. Asad Zaman highlights the operational difficulty of telling investors about the actual steps involved; e.g. "I'm going to do a reorg and I'm then going to change my strategy that's actually going to increase churn... That's a war at the board level." * Title changes don't fix structural issues. Asad Zaman and Sam Jacobs advise revenue leaders against accepting Gong's new "Chief Revenue Architect" title because "it's going to hurt your career moving forward... This sounds like you were demoted to rev ops to me." Your Hosts: Host: Host: Host: Topline is more than a Podcast! Subscribe to Topline Newsletter: https://www.joinpavilion.com/topline-newsletter Watch on the YouTube channel: 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 Intro 02:04 The Citrini Report Examined 07:05 Startups vs. Innovator's Dilemma 12:35 SaaS Valuation Repricing 15:29 Losing Pricing Leverage to AI 21:29 Is White Collar Work Dead? 25:10 Margin Compression Strategy 31:17 Restructuring Engineering Teams 35:09 Microsoft's Product Pivot 39:54 How AI Improves CEO Workflow 44:50 Gong's Chief Revenue Architect 51:17 Why the CRO Title Matters 55:14 AI Predictions Looking Ahead /episode/index/show/ed89b0ae-e358-414a-9719-bac1c505b717/id/40267460

SPOTLIGHT: Raising $55M When You’re Not “AI-Native” | Nick Turner, CEO @ Dreamdata 02/26/2026

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