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Pavilion

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.

  1. 23h ago

    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

  2. 3d ago

    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

  3. 5d ago

    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

    AI Marketing Master: The 'AI CMO' is a Beautiful Lie | Marc Ferrentino, CEO @ Quotient

  4. Jul 17

    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

  5. Jul 12

    $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: https://www.joinpavilion.com/topline-slack 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

    $300M Operator: "70% Of The Executive Playbook Is Obsolete" | Katie Bullard, Board Member & Strategic Advisor

  6. Jul 5

    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

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

  7. Jun 28

    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: https://toplinemedia.substack.com/ Subscribe to the 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 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

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

  8. Jun 21

    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: 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 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

    The $1M Employee Is Here: Why ClickUp Replaced 22% Of Its Team With AI | Gaurav Agarwal, COO @ ClickUp
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4.8
out of 5
56 Ratings

About

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.

Information

  • Creator
    Pavilion
  • Years Active
    2023 - 2026
  • Episodes
    256
  • Rating
    Explicit
  • Copyright
    © 012671
  • Show Website
    Topline

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