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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.

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  • 27 episodes
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  • Sunday · 1 hr 11 min

    Forget Growth. Your Valuation Depends On Your AI Story | Tomasz Tunguz, GP @ Theory Ventures

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

  • September 3 · 25 min

    SPOTLIGHT: Surviving the Inbox Apocalypse | Evan Huck, CEO & Co-Founder @ UserEvidence

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

  • August 30 · 1 hr 18 min

    How To Make Your ARR 20% More Valuable To Investors | Keenan, CEO @ A Sales Growth Company

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

  • August 27 · 32 min

    SPOTLIGHT: AI Isn't Just Faster Translation, It's a $40B Tug-of-War for Global Attention. | Bryan Murphy, CEO @ Smartling

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

  • August 23 · 1 hr 13 min

    The Unwritten Rules of CRO Survival | Rick Smolen, CRO @ ShipHero

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

  • August 20 · 29 min

    SPOTLIGHT: He Missed Quota 5 Times in 25 Years. Here's the System Behind That.| Mike Carpenter, CEO & Co-Founder @ Xfactor

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

  • August 16 · 1 hr 10 min

    Sales Millionaires Are Back… Wasn't AI Supposed to Destroy This Job?!

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

  • August 13 · 20 min

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

    In this episode of Topline Spotlight, Sam Jacobs sits down with Snehal Nimje, co-founder and CEO of Outdoo, to talk about one of the hardest calls an early-stage founder can make: narrowing focus when leads are coming in. Snehal breaks down how Outdoo went from trying to serve every mid-market and enterprise buyer to getting much more specific about where the product was truly essential. They get into why usage dropped, what customer conversations revealed, how the team handled the internal shift, and what changed once they focused on insurance and finance use cases where compliance and ramp speed mattered most. They also talk about: - Why enterprise readiness starts with architecture, compliance, and security - How to tell the difference between interest and real traction - What founders miss when they chase every lead - Where defensibility really comes from in AI Chapters: 00:00 Intro 00:46 Meet Snehal Nimje and Outdoo 04:55 Why selling to everyone nearly derailed the business 06:51 Finding the customers who truly need your product 08:54 The hard decision to narrow their ICP 11:00 How focus accelerated enterprise growth 13:09 Advice for founders struggling to find product-market fit 15:36 What creates a moat in the AI era? 17:13 Why workflow—not AI models—is the real competitive advantage 18:51 Snehal's biggest business inspiration 19:38 Where to find Snehal and Outdoo Try Outdoo: outdoo.ai If you're building an early-stage company and trying to find traction without turning your product into a Frankenstein, this one's worth your time. Subscribe for more founder stories, operator lessons, and go-to-market conversations from Topline.

  • August 9 · 1 hr 14 min

    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

  • August 2 · 1 hr 14 min

    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

  • July 28 · 24 min

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

    AI isn't just changing sales. It's completely rewriting how revenue teams operate. In this episode of Topline Spotlight, Sam Jacobs sits down with Justin Shriber, CEO of Terret AI, to break down how modern revenue organizations are using AI to improve forecasting, shorten sales cycles, ramp reps faster, and operationalize winning sales behavior in real time. Justin shares: Why traditional sales enablement is broken How AI helped reduce rep ramp time by 40% The "answer-to-action" engine powering modern RevOps The hidden dangers of decentralized AI adoption Why companies are struggling with inconsistent AI-generated data The real debate: build your own AI stack vs buy from vendors How leading teams are using AI agents today One of the most interesting conversations in GTM right now. If you're a CRO, RevOps leader, founder, or GTM operator trying to understand where AI is actually delivering value, this episode is worth your time. Chapters: 00:00 Intro 00:40 Meet Justin Schreiber and Terret 04:17 How AI is changing sales productivity 06:07 The biggest problem in revenue execution 09:37 Why great strategies never get executed 11:01 Building AI that's secure, accurate, and scalable 13:32 Buy vs. build: The future of enterprise AI 16:25 Why AI needs centralized governance 17:35 Jurassic Park, AI agents, and organizational chaos 20:15 Justin's biggest inspirations for building great companies 22:58 Where to find Justin and Terret Try Terret: terret.ai

  • July 26 · 1 hr 22 min

    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

  • July 24 · 21 min

    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

  • July 21 · 24 min

    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

  • July 19 · 1 hr 13 min

    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

  • July 17 · 23 min

    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

  • July 12 · 1 hr 14 min

    $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

  • July 5 · 1 hr 10 min

    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

  • June 28 · 1 hr 15 min

    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

  • June 21 · 1 hr 16 min

    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

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