Topline
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- 12. Nov. 2026
Über den Podcast
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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SPOTLIGHT: Why Good Marketing Teams Still Fail with John Short | John Short, CEO @ Compound Growth Marketing
More marketing spend doesn't always mean more growth. And having the right people doesn't necessarily mean you have the right structure. As customer acquisition costs rise and traditional B2B channels become …
Shownotes
More marketing spend doesn't always mean more growth. And having the right people doesn't necessarily mean you have the right structure.
As customer acquisition costs rise and traditional B2B channels become increasingly competitive, companies need to rethink how they approach performance marketing, demand generation, and team structure.
John Short, CEO of Compound Growth Marketing, spent more than a decade building performance marketing teams at companies like Workable, Monster.com, and LogMeIn before launching his own agency eight years ago. Today, he helps high-growth B2B companies build more predictable and efficient growth engines.
In this episode of Topline Spotlight, Sam Jacobs sits down with John to discuss the changing B2B marketing landscape, the opportunities beyond LinkedIn and Google, and the operational lessons he's learned while scaling his own business.
What we get into: - Why B2B companies need to diversify beyond LinkedIn and Google - The growing opportunity in CTV, Meta, Reddit, and other channels - How to find more efficient customer acquisition opportunities - Why specialization gives marketing agencies a competitive advantage - Why roles and responsibilities matter more than traditional org charts - How marketing teams can connect individual KPIs to company-wide growth
Chapters:
00:45 Intro to John Short and Compound Growth Marketing 03:10 The Power of Specialization in B2B Marketing 04:27 Why B2B Companies Need to Look Beyond LinkedIn 06:19 The Opportunity in Connected TV Advertising 08:15 Customer Acquisition Costs and Finding Efficiency 09:20 Lessons From Building a Marketing Agency 10:57 Why Roles and Responsibilities Beat Traditional Org Charts 15:06 Connecting Marketing KPIs to Business Growth 20:02 The Books and Ideas That Influenced John 21:00 Where to Find John Short Try Compound Growth Marketing: compoundgrowthmarketing.com
The Great Tech Selloff (Silicon Valley Investor Explains) | Rajeev Dham, MD @ Sapphire Ventures
Before today's conversation, Sam, AJ and Asad share a few words in memory of Adam Robinson. Rajeev Dham, Managing Director at Sapphire Ventures (a $10 billion venture firm), joins Sam Jacobs, AJ Bruno, and Asad …
Shownotes
Before today's conversation, Sam, AJ and Asad share a few words in memory of Adam Robinson.
Rajeev Dham, Managing Director at Sapphire Ventures (a $10 billion venture firm), joins Sam Jacobs, AJ Bruno, and Asad Zaman to make sense of the recent tech selloff and what it means for AI investing. Topics include why Rajeev sees a "duration mismatch" as a core challenge, how the funding bar has changed after months of $50 to $100 million decisions made in days, and why AI application companies are growing from $15 to $100 million in revenue even as steady-state gross margins may settle closer to 30%. Plus, advice for pre-AI SaaS companies, why private equity is still frozen, a data company that went from zero to a $900 million run rate, whether the models will eat the harness, what the Anthropic IPO means for everyone else, and whether go-to-market AI can ever be more than a spam cannon.
Key Takeaways:
- The selloff is about timing, not the technology. The AI buildout is expensive, and Wall Street now wants to see it in S&P 500 earnings, not just in Anthropic's run rate. "I'm a believer. I think there's just a duration mismatch," said Rajeev, who compares it to Amazon's AWS buildout rather than the dot-com crash: "I think it could be a 6-month, 9-month period… when this mismatch needs to be reconciled." - AI margins may never look like SaaS, and that can be fine. "I don't know if we're going to have the 78% margin businesses. It could very well be you have a 30% gross margin business," said Rajeev. What matters is gross profit dollars: "if you could charge 30 to 40% of $10,000 per person per year versus $1,000 versus 80% of $1,000, your gross profit dollars are a lot bigger." His bet: "I think ASPs will grow by 10x." - When everything grows fast, growth stops being the signal. "I don't even look at growth rates," said Rajeev. The founder used to be maybe a 30 to 50% weight in a growth-stage decision; "Now it's an 80, 90% weight, even at sometimes a billion of run rate." He looks for founders who rebuilt their product "after the Opus 4.5 moment in December" to keep winning share. - For pre-AI SaaS companies, the advice is to burn the boats. Rajeev told one founder running a cash flow breakeven $300 million business that "whether you grow 24% or 18%, it doesn't matter," and to "hire a COO, a private equity-like COO just to run that business" while the founder builds the AI products and eventually merges the two.
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: Rajeev Dham, Managing Director at Sapphire Ventures - https://www.linkedin.com/in/rajeev-dham-79332812/
Topline is more than a podcast:
Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Check us out on YouTube for the #1 video podcast for founders, operators, and investors in B2B tech: https://www.youtube.com/@TOPLINE-Media Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack
Chapters: 00:00 Introducing Rajeev Dham 01:04 In memory of Adam Robinson 05:51 The Great Tech Selloff 10:35 How the Funding Bar Has Changed 12:46 Why AI Apps Grow So Fast 15:47 The 30% Gross Margin Future 21:28 When Does the AI Land Grab End? 24:38 Advice for Pre-AI SaaS Companies 26:53 Why Private Equity Is Still Frozen 35:11 What Gets a VC Excited Now 39:12 The Unfundable $9M to $38M Company 45:17 Founders Who Pivot at Warp Speed 49:43 Will the Models Eat the Harness? 57:50 Anthropic and the New IPO Bar 59:44 Is Go-to-Market AI a Spam Cannon?
Sources & Attribution:
Clip: https://youtu.be/TNq79c8QNlg Clip: https://youtu.be/lgMTA5GU7TE Article: https://www.axios.com/2026/10/26/anthropic-ipo
SPOTLIGHT: AI Is Rewriting Sales. Are Your GTM Teams Ready? with Dan Lee of Nooks | Dan Lee, Co-Founder and CEO @ Nooks
AI has transformed software engineering. It's changing nearly every knowledge-based profession. So why hasn't sales changed at the same pace? Dan Lee, Co-Founder and CEO of Nooks, is building what he believes …
Shownotes
AI has transformed software engineering. It's changing nearly every knowledge-based profession.
So why hasn't sales changed at the same pace?
Dan Lee, Co-Founder and CEO of Nooks, is building what he believes will power the next generation of go-to-market teams: AI agents and revenue infrastructure that execute across the entire revenue lifecycle.
In this episode of Topline Spotlight, Sam Jacobs sits down with Dan to unpack how Nooks evolved from a virtual collaboration platform into an AI-powered revenue platform and why the future of sales will look fundamentally different.
What we get into: - Why sales is the next profession to be transformed by AI - How AI is changing software development and product velocity - Why sales reps need to become revenue AI consultants - Serving demand vs. generating demand - What AI agents can automate—and where humans still matter - Why the future belongs to highly consultative, 10X sales reps
Chapters:
00:36 Intro to Dan Lee and Nooks 01:23 Why Sales Is the Next Job AI Will Transform 03:01 The Evolution of Nooks 05:55 The Future of Software: The Barbell Effect 08:01 Why Customer Outcomes Matter 10:22 How AI Is Changing Software Engineering 12:08 Retraining Sales Teams for the AI Era 13:22 Serving Demand vs. Generating Demand 14:36 The Future of Human Salespeople vs. AI Agents 17:01 How to Be the Right CEO for the Moment 19:06 Building Proactive AI Agents for Sales 19:46 Where to Find Nooks Try Nooks: nooks.ai
"Zero Chance" AI Bubble Doesn't Pop (Here's Who's Safe) | Geoffrey Moore, Author & Venture Partner
Geoffrey Moore, author of Crossing the Chasm (over 1 million copies sold) and Zone to Win, and an advisor to the CEOs of Microsoft, Salesforce, and Cisco, joins Sam Jacobs, AJ Bruno, and Asad Zaman for a first …
Shownotes
Geoffrey Moore, author of Crossing the Chasm (over 1 million copies sold) and Zone to Win, and an advisor to the CEOs of Microsoft, Salesforce, and Cisco, joins Sam Jacobs, AJ Bruno, and Asad Zaman for a first appearance on Topline. Topics include whether agentic AI has crossed the chasm, why there's "zero chance" the AI bubble doesn't pop (and who will make it out the other side!), how startups win in a downturn, and how the Zone to Win framework is useful to help move AI pilots out of incubation and into the core business. Plus, a closer look at the SaaS-pocalypse and Salesforce's platform play, trapped value as the only durable moat, the hierarchy of powers behind today's valuations, whether AI has to eat the labor budget to pay off, and whether Geoffrey would buy the Anthropic IPO at a $2 trillion valuation.
Key Takeaways:
- The AI bubble will pop, but the category leaders will be fine. "There is zero chance that this bubble doesn't pop. We're so far over our skis in terms of valuations, it's crazy," said Geoffrey, pointing to circular financing that echoes the dot-com era. The survivors are the number 1 and number 2 players: "The winners are actually gonna win… But 3, 4, 5, 6, 7, 8, 9, 10? No." - Most AI initiatives are stuck in the incubation zone. "People were piloting like crazy and having great success" said of the last two years of enterprise AI pilots... but then they got stuck. The Zone to Win fix is to make the productivity zone customer zero, re-engineering internal shared services first, then bring the new technology to the sales team use case by use case rather than all at once. - Where are moats today? Geoffrey points to trapped value as one type of moat. Trapped value analysis is a method to continually discover the new ways you can be irreplaceable to your customers, and stay ahead of the market. - The ROI from AI won't come mainly from cutting headcount. "I think they're coming from quality improvement and latency reduction, not from labor reduction," said Geoffrey. For the next decade, probabilistic agents will sit in front of deterministic systems of record with a human checking in between, because "AI can be accountable, but it cannot be responsible."
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: Geoffrey Moore, Board Member, Venture Partner, Author - https://www.linkedin.com/in/geoffreyamoore/
Topline is more than a podcast:
Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Check us out on YouTube for the #1 video podcast for founders, operators, and investors in B2B tech: https://www.youtube.com/@TOPLINE-Media Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack
Chapters: 00:00 Introducing Geoffrey Moore 02:01 Has Agentic AI Crossed the Chasm? 03:59 Will the AI Bubble Pop? 08:59 Startups That Win in a Downturn 12:00 The Zone to Win Framework 17:51 Getting AI Pilots Out of Incubation 19:21 Is Every SaaS Company Under Threat? 21:35 Zone Offense vs. Zone Defense 25:12 Salesforce, Headless and Platforms 33:34 Trapped Value Is the Real Moat 43:00 The Hierarchy of Powers 49:14 Can OpenAI and Anthropic Stay on Top? 53:13 Will AI Eat the Labor Budget? 01:02:07 Speed of Adoption vs. Innovation 01:04:57 Bulls and Bears
SPOTLIGHT: Solving SaaS Pricing Challenges with Pricing I/O Founder Marcos Rivera | Marcos Rivera, Founder and CEO @ Pricing I/O
Marcos Rivera, Founder and CEO of Pricing I/O, has grown his solo consultancy into a team of pricing experts serving B2B SaaS companies. But building a specialized business came with a major challenge: finding …
Shownotes
Marcos Rivera, Founder and CEO of Pricing I/O, has grown his solo consultancy into a team of pricing experts serving B2B SaaS companies. But building a specialized business came with a major challenge: finding people who could do more than understand pricing—they needed to connect customer value, business strategy, and software.
In this episode of Topline Spotlight, Marcos joins Sam Jacobs and Asad Zaman to explain how he rethought his hiring process, from defining what success looks like to using practical case studies and structured onboarding. He also shares his perspective on pricing strategy, customer retention, and why companies need to ensure their pricing keeps pace with the value they deliver.
Marcos talks about:
- Why pricing should be revisited as your product and customer experience evolve - How underpricing can influence customers' perceptions of quality - Why giving customers more features won't necessarily solve churn - How to evaluate candidates' problem-solving skills through structured case studies - Why a thoughtful onboarding plan can help new hires reach productivity faster - How trust shapes the way you serve clients and build a business
Chapters
00:00 Topline Introduction 01:26 Introduction to Topline Spotlight 01:53 Meet Marcos Rivera, Founder and CEO of Pricing I/O 04:45 Common Misconceptions About Pricing 14:11 Solving a Critical Business Problem: Hiring the Right Talent 23:01 Reflections and Recommendations 25:02 Where to Find Marcos Rivera 25:39 Closing Remarks Try Pricing I/O: pricingio.com
The Man Who Led 100+ CROs (Even OpenAI's) | John McMahon - 5x Post-IPO CRO / The GOAT
John McMahon, a five-time public company CRO whose team at PTC created MEDDIC, joins Sam Jacobs, AJ Bruno, and Asad Zaman on building enterprise sales teams that last. Topics include the PTC lineage that has …
Shownotes
John McMahon, a five-time public company CRO whose team at PTC created MEDDIC, joins Sam Jacobs, AJ Bruno, and Asad Zaman on building enterprise sales teams that last. Topics include the PTC lineage that has produced over 100 CROs, including OpenAI's Dali Rajic, why he hires on characteristics over resumes, whether a CRO who never carried a bag can lead, and how first-time CROs should work with their CEO. Plus, capped commissions at Anthropic, why AI makes lazy reps lazier, what conversational intelligence tools miss in deal qualification, and quick takes on Dali, Carlos at Harness, Dev Ittycheria, and Chris at Cognition.
Key Takeaways:
- Hire on characteristics, not resumes. John sorts candidates by skills, knowledge, experience and characteristics, and the last one is the hardest to teach: "I've always hired on characteristics. So I'll take someone with less experience but great characteristics." He looks for intelligence, drive, coachability, adaptability and integrity, because when a hire fails, "it's always a character flaw." - Don't take the CRO seat before you're ready. John once refused a promotion Dali pushed him for: "I told him, I'm not gonna do that to you because you're not ready… you're gonna fail. Your ego's not gonna be able to take it." For John, readiness comes down to whether you can recruit, coach, and lead people who actually want to follow you. - Talk to the CEO as a partner. Plenty of first-time CROs hold the C-level title without acting like the CEO's peer, and John coaches them to speak up: "You're the CRO. You have a fiduciary responsibility. Tell the CEO specifically what you think is wrong with the business." Blaming revenue problems on the product "is a non-starter," so come with a solution and talk like a business owner. - AI hasn't changed the methodology. John sees AI mostly as a research tool, and "it makes the really good sales reps better, and it makes the lazy sales reps lazier." He is just as blunt about conversational intelligence: "All they're doing is verifying that something was said, but there's no true qualification." Qualifying still means knowing whether you're talking to a champion, a coach, or the enemy.
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: John McMahon, 5x Public Company CRO - https://www.linkedin.com/in/johnmcmahon1/
Topline is more than a podcast:
Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Check us out on YouTube for the #1 video podcast for founders, operators, and investors in B2B tech: https://www.youtube.com/@TOPLINE-Media Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack
Chapters: 00:00 Introducing John McMahon 02:18 The PTC Sales Leadership Tree 07:20 Hiring on Characteristics, Not Resumes 12:10 Should a CRO Have Carried a Bag? 16:50 Capped Commissions vs. Equity Upside 19:05 When Are You Ready to Be CRO? 22:56 How CROs Should Evaluate the CEO 34:52 AI and Sales Methodology 38:10 AI Call Tools Don't Qualify Deals 40:52 MEDDIC and Bigger Buying Groups 42:51 The Art and Science of Selling 48:47 Coaching Mark Roberge at HubSpot 59:31 Managing Heads Like a Bond Portfolio 01:03:42 Hiring Batting Average and Ramp Time 01:09:40 Rapid Fire: Dali, Carlos, Dev, Chris
SPOTLIGHT: Untangling Tech Debt and Finding Product-Market Fit with Russ Mikowski of SurePeople | Russel Mikowski, CEO @ SurePeople
Russ Mikowski, CEO of SurePeople and longtime revenue leader in tech, never planned to become a CEO. Recruited to lead a 10-year-old company into its next stage of growth, he faced technical debt, an unfocused …
Shownotes
Russ Mikowski, CEO of SurePeople and longtime revenue leader in tech, never planned to become a CEO. Recruited to lead a 10-year-old company into its next stage of growth, he faced technical debt, an unfocused ideal customer profile (ICP), and the challenge of turning the company's potential into a scalable business.
In this episode of Topline Spotlight, Russ joins Sam Jacobs and AJ Bruno to discuss the decisions behind SurePeople's transformation, including rebuilding parts of its product, narrowing its target market, and resisting custom requests that could pull the business off course.
Russ talks about:
- How to identify and focus on the customers your product serves best - When rebuilding is a better option than refactoring - Why saying no to the wrong opportunities can protect long-term growth - How to keep a team aligned through organizational change - Why great leaders attract and retain talent by removing obstacles
Chapters
00:00 Introduction to Topline Spotlight 01:54 Meet Russ Mikowski, CEO of SurePeople 03:00 SurePeople and the PRISM Assessment 05:51 Russ's Journey to CEO 08:55 Tackling Technical Debt and Rebuilding the Product 12:01 Narrowing the ICP and Finding Market Focus 14:50 Communicating Change and Aligning the Team 17:53 Leadership Lessons from a Mentor 24:00 Where to Find Russ Mikowski and SurePeople Try SurePeople: surepeople.com
$682M Public CEO: "The Magic of 80% Gross Margin" | CEO @ Yext, Michael Walrath
Michael Walrath, CEO of Yext, is back on Topline to explain how Yext went from breakeven to 31% EBITDA margins on an 80% gross margin business, after halving its headcount and using its balance sheet to buy …
Shownotes
Michael Walrath, CEO of Yext, is back on Topline to explain how Yext went from breakeven to 31% EBITDA margins on an 80% gross margin business, after halving its headcount and using its balance sheet to buy back roughly 35% of every share it ever issued. He joins Sam Jacobs, AJ Bruno, and Asad Zaman to argue that the old rules of business still apply: why VC math and founder math are different games, why employees lose the most when an overvalued startup like Airtable lands far below its peak valuation, and why this market feels like 2004. Plus, why Yext stopped doing earnings calls and replaced most stock comp with cash, why cutting the bottom half of a sales team can raise bookings, and how Yext is blurring the lines between AEs, account managers, CSMs and sales engineers.
Key Takeaways:
- Real profitability turns any growth into fuel. As Michael put it, "when you're actually profitable, like really profitable, then any growth becomes hugely accretive." With 80% gross margins and 31% EBITDA margins, "Every incremental dollar, I can spend 45 cents of it and not affect my margins in any way," so a left-for-dead software company can fund its own growth whatever the market says it's worth. - Chase growth only where it actually exists. "Nothing's more powerful than growth at creating value. Nothing is more destructive to value than chasing growth when the growth isn't there," said Michael. Airtable avoided the trap by leaving its cash on the balance sheet, while Yext once spent 74% of revenue on sales and marketing into a declining growth rate. - Cutting your weakest sellers can grow bookings. When 20% of reps make quota and the bottom half brings in 20% of bookings, the spreadsheet says cutting them costs you that 20%. "It's not even close to true. It's the opposite," said Michael (his numbers were illustrative). Yext now has fewer, better sellers, and is "effectively eliminating all distinction between go-to-market roles" in favor of teams that own books of customers. - Stock comp can turn your own employees into sellers of your stock. Most people sold their RSUs the day they vested, and every quarterly issuance meant the company sold shares to cover taxes too. "The last thing you need are more sellers of your stock every quarter," said Michael, so Yext now pays most employees more cash and points long-term believers to its employee stock purchase plan.
Connect with the Hosts & Guests:
Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: Michael Walrath, CEO at Yext - https://www.linkedin.com/in/michael-walrath-b63166/
Topline is more than a podcast:
Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Check us out on YouTube for the #1 video podcast for founders, operators, and investors in B2B tech: https://www.youtube.com/@TOPLINE-Media Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack
Chapters: 00:00 Introducing Mike Walrath 03:13 VC Math vs Founder Math 04:46 Why Employees Lose the Most 09:05 Why This Market Feels Like 2004 12:04 31% EBITDA Makes Growth Accretive 16:12 Why Mike Is a Jobs Bull 19:48 What Airtable Got Right 28:19 Hot Startup Equity Is a Lottery 41:37 Yes, You Can Attract Talent 44:16 The Road to 30% EBITDA Margins 47:45 No Earnings Calls, No IR Team 51:52 Replacing Stock Comp With Cash 54:41 Cut the Bottom 50% of Sellers 57:19 Collapsing Go-to-Market Roles 01:01:22 From PE Guy Back to Growth
SPOTLIGHT: How Rick Smolen Built Confidence Leading Outside of Sales | Rick Smolen, CRO @ ShipHero
When Rick Smolen stepped into the CRO role at ShipHero, he took on responsibility for the entire customer lifecycle, from marketing and partnerships to customer success and support. With a background primarily …
Shownotes
When Rick Smolen stepped into the CRO role at ShipHero, he took on responsibility for the entire customer lifecycle, from marketing and partnerships to customer success and support.
With a background primarily in sales, he had to learn how to lead functions outside his expertise without needing to have all the answers.
In this episode, Rick joins Sam Jacobs to discuss the leadership lessons that came with that transition, from asking better questions to building trust with his team. He also explains how to learn from failure, navigate setbacks, and focus on what you can control as a leader.
Rick talks about:
- Why curiosity makes you a stronger cross-functional leader - How to challenge your team without micromanaging - Why experimentation requires accepting failure - What leaders should focus on when business results fall short - How to prioritize important work that rarely feels urgent
Chapters
00:00 Introduction to Rick Smolen and ShipHero 01:10 What ShipHero Does 05:14 Rick's Career Journey 07:50 From Sales Leader to CRO: The Biggest Shift 10:49 Why Curiosity Makes You a Better Leader 16:23 Building a Leadership Team That Learns and Experiments 17:54 Evaluating Leadership Beyond Revenue 22:50 Rick's Book Recommendation: The 7 Habits of Highly Effective People 24:53 Where to Find Rick Smolen Try ShipHero: shiphero.com
AI Revenue Is Real. But Will It Last? | Amy Konary, Founder & Chair, Subscribed Institute @ Zuora
Amy Konary, Founder & Chair of The Subscribed Institute at Zuora, coined the term SaaS as an IDC analyst around 2000, when her first forecast sized the whole market at $40 million. She joins Sam Jacobs, AJ …
Shownotes
Amy Konary, Founder & Chair of The Subscribed Institute at Zuora, coined the term SaaS as an IDC analyst around 2000, when her first forecast sized the whole market at $40 million. She joins Sam Jacobs, AJ Bruno, and Asad Zaman for the first in-person Topline to ask whether AI company economics are a house of cards, and whether circular financing and double counting are real problems. Plus, why POCs have stopped being a pipeline signal, experimental revenue versus true ARR, a new leverage index for sticky revenue, tokens versus credits, and how close outcome pricing can really get.
Key Takeaways:
- Treat POCs as a weak pipeline signal. As Amy put it, "it used to be that hands-on product was a really good signal from a pipeline perspective, but everyone's doing POCs just to kick the tires, but actually has no mandate to buy." Many are free, production-ready builds, and very few convert. - Usage alone won't tell you which revenue will last. Amy scores customers on scope and workflows, trust in the system's outputs, and how much of their own context they upload, because "you can have 2 customers with the exact same usage, but very different leverage." Low leverage means "That revenue is less durable." - Pure usage pricing can leave you as exposed as seats did. "If you're just tracking usage, and usage is highly experimental, and usage decreases over time as people optimize the tools, you're in the same vulnerable position you were in with seats," said Amy, who expects hybrid models with a smaller, trackable outcome piece. - Build for durability without rigidity. "So I think there's a difference between durability and rigidity," Amy said, and her metaphor is bamboo: one of the strongest construction materials, yet flexible, anchored by a clear focus on the customer's progress.
Connect with the Hosts & Guests:
Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: Amy Konary, Founder & Chair, The Subscribed Institute at Zuora - https://www.linkedin.com/in/amykonary/
Topline is more than a podcast:
Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Check us out on YouTube for the #1 video podcast for founders, operators, and investors in B2B tech: https://www.youtube.com/@TOPLINE-Media Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack
Chapters: 00:00 Introducing Amy Konary 01:43 From ERP Sales to Industry Analyst 03:33 How Amy Konary Named SaaS 08:03 How Salesforce Taught the Street SaaS 10:31 Building Durable Companies for AI 11:52 Does Gross Margin Still Matter? 15:10 Who Is Checking AI Company Math? 17:03 Circular Financing and Double Counting 18:30 Is AI a House of Cards? 21:49 Durability Versus Rigidity 29:19 Be Careful About Your POCs 33:40 The Leverage Index for Sticky Revenue 39:12 SaaS Companies Moving Into Services 41:59 Tokens, Credits and Outcome Pricing 48:32 P(doom) and Raising Kids With AI
SPOTLIGHT: How CEO Sam Jacobs Is Redefining Pavilion's Identity | Sam Jacobs, Founder & CEO @ Pavilion
When Sam Jacobs founded Pavilion, formerly Revenue Collective, he set out to build a private community for operators in a startup world that traditionally celebrated founders and overlooked the people running …
Shownotes
When Sam Jacobs founded Pavilion, formerly Revenue Collective, he set out to build a private community for operators in a startup world that traditionally celebrated founders and overlooked the people running the business. But as Pavilion grew to 10,000+ members, the very thing that made the community valuable began to get diluted. In this special Topline Spotlight episode, Sam joins co-hosts AJ Bruno and Asad Zaman to talk about what happened, why removing the qualification barrier was a mistake, and what it took to bring Pavilion back to its original vision.
Sam talks about: - Why rapid growth can dilute what makes a community valuable - How LinkedIn and Slack helped Pavilion scale faster than expected - What happened when exclusivity gave way to openness - Why reversing course became harder once the community had grown - The importance of having a long-term vision instead of chasing immediate growth - Why building something great requires patience and restraint Chapters: 00:00 Introduction 00:42 Business Challenge of the Last 24 Months 01:29 What Is Pavilion? 02:43 Launching Pavilion Gold 04:01 Why the Community Scaled So Quickly 06:51 LinkedIn and Slack as Growth Drivers 07:02 Shifting Culture of Openness Among GTM Leaders 08:04 The Consequences of Losing Focus 10:54 The Biggest Mistake: Removing the Qualification Barrier 11:32 The Challenge of Reversing Course 13:46 Continued Opportunity for Operator Advocacy 15:00 Solving the Challenge: Long-Term Vision 15:54 Building a 3-Year Vision for Pavilion 16:08 Importance of Patience in Building Exclusive Communities Try Pavilion: joinpavilion.com
Turning AI Tokens Into ROI (That You Can Measure) | CEO @ Paid, Manny Medina
Manny Medina, Co-Founder and CEO of Paid, the monetization platform for AI agents, and the founder who took Outreach from nothing, joins Sam Jacobs, AJ Bruno, and Asad Zaman in person on how to price AI agents …
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Manny Medina, Co-Founder and CEO of Paid, the monetization platform for AI agents, and the founder who took Outreach from nothing, joins Sam Jacobs, AJ Bruno, and Asad Zaman in person on how to price AI agents once seats stop making sense. Topics include why every SaaS company needs its own agents before someone else's run on its MCP layer, why a token is the wrong unit of value, and the itemized phone bill every agent builder owes its buyers. Plus, why fixed-price deals win logos but stall expansion, the case for 40% to 60% gross margins in the agent era, and what Satya Nadella told Manny in a green room. Key Takeaways: - Price the work your agent does, not the seats it fills. In SaaS you sell 100 seats, procurement sees 20 in heavy use, and the renewal shrinks to 50. With agents, "if you've sold 100 seats and only 2 were hyper-users, you don't care because you're charging for all the uses and all the value those 2 seats were getting." For now that pricing lives between effort and output, because true outcome pricing needs attribution, and as Manny put it, "Attribution is really hard." - Make the bill readable before you argue about ROI. Manny compares it to the old itemized phone bill, where you went straight to the biggest line and asked, "Did I really call Pakistan from New York?" Tokens can't play that role: "A token should not be a unit of value for charging because a token is really kind of like the inside secret." Show the buyer the research, deck, or analysis the agent produced, because "explainability is like the first rung in the ladder." - Fixed pricing is easy money that boxes you in at renewal. Enterprises are buying one of each right now, so "new logo is not hard. Expansion is hard." Teams that land logos on fixed price hit the first renewal with nowhere to go, which is why Paid opens with a monetization consultant and takes a percentage of revenue: "You grow, I grow." - Plan for thinner margins and narrower markets. Manny learned Amazon's margins cold (books 20%, electronics 7%, jewelry 3%) and calls SaaS's 70 to 80% an anomaly of cheap money: "I feel like a normal, you know, software business will be running on 40% margins, 60% tops."
Connect with the Hosts & Guests: Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: Manny Medina, Co-Founder & CEO at Paid - https://www.linkedin.com/in/medinism/ Topline is more than a podcast: Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Check us out on YouTube for the #1 video podcast for founders, operators, and investors in B2B tech: https://www.youtube.com/@TOPLINE-Media Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack Chapters: 00:00 Introducing Manny Medina 01:37 What Paid Is Building 04:38 Will All Software Go Agentic? 06:35 The 100-Seat Renewal Problem 10:02 An Itemized Phone Bill for Agents 13:33 Why Outcome Pricing Takes Time 19:04 Open Source vs. Frontier Models 26:41 Pricing Agents Is an NRR Problem 33:11 Why Manny Won't Build Workflows 35:39 Fundraising Lessons From Outreach 41:10 Life Is Path Dependent 45:46 Culture Is the Exhaust of Winning 47:50 Is AI Spend Still Experimental? 58:22 The End of 80% Software MarginsSPOTLIGHT: The Problem With Your CRM Nobody Talks About | Ramin Heydari, CEO & President @ XYZies
You have the CRM. You have the data. You have the sales team. You have the AI tools. So why does everything still feel broken? Ramin Heydari, CEO & President of XYZies, has spent more than 30 years building …
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You have the CRM. You have the data. You have the sales team. You have the AI tools. So why does everything still feel broken? Ramin Heydari, CEO & President of XYZies, has spent more than 30 years building businesses across telecom, sales, distribution, and technology.
In this episode of Topline Spotlight, he explains why fragmented systems can become one of the biggest obstacles to growth and why AI requires businesses to rethink how they operate, not simply add another tool.
Sam Jacobs sits down with Ramin to unpack the shift from traditional growth to 10X thinking, the problem with scattered data and sales systems, and how AI can create real-time visibility and coaching across an organization.
What we get into:
- Why businesses need to think beyond traditional growth - Why adding AI to existing software isn't enough - The hidden cost of fragmented systems and data - How AI can provide real-time coaching and performance feedback - Why continuous improvement matters more than occasional reviews - What a truly AI-powered CRM could look like - The leadership principle: "The future belongs to those who can see it before it becomes obvious."
Chapters:
02:01 Why XYZ Exists And Why "The Details" Matter 03:27 Building the Smarter Home With AI 04:10 Information Overload and Better Decisions 07:32 Why Businesses Need to Think 10X 09:47 The Problem With Too Many Systems 10:15 The Human Side of the Technology Problem 10:58 The "Dream CRM" 12:49 Real-Time AI Coaching and Continuous Improvement 15:07 The Hidden Cost of Enterprise Software 17:56 Ramin's Leadership Lessons 19:20 Where to Find XYZies 19:46 Outro Try XYZies: xyzies.com
If the AI Money Dries Up, Which Companies Burn?
Harvey's gross margin fell from roughly positive 50% at the start of 2026 to negative 50% by June, so every $1 of revenue cost $1.50 to deliver. Sam Jacobs, CEO of Pavilion, AJ Bruno, CEO of QuotaPath, and Asad …
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Harvey's gross margin fell from roughly positive 50% at the start of 2026 to negative 50% by June, so every $1 of revenue cost $1.50 to deliver. Sam Jacobs, CEO of Pavilion, AJ Bruno, CEO of QuotaPath, and Asad Zaman, CEO of STA, go hosts-only on when AI growth justifies margins like that, why open weight models are no substitute for frontier intelligence, and what happens to the application layer if the exuberant market funding it goes away. Plus, AJ's 100x raise from 2021, a 68% jump in tech M&A and what it means for employee equity, and a Bulls and Bears round on AI catastrophe before 2031.
Key Takeaways:
- Negative gross margins can be a phase if there's a way out. Sam's straw man: "Above 200% growth, I can tolerate bad margins temporarily if you can show me you have a path to a good business." Between 100% and 200% he wants "a clear improving trajectory," and below 50% the margins have to be good.
- Cheaper models fix the margin line but can break the product. Asad likened the switch to open weight models to "going from hiring people only from Harvard to then going and hiring people from the worst university you can find or some mid-tier university and saying it's the same thing." That leaves application companies "completely at the behest of these model companies."
- The 2021 hangover is still on cap tables. AJ raised QuotaPath's Series B "at a 100x valuation in '21," but with SaaS multiples at "1x or less than 1x," he said, "If I wanted to go sell QuotaPath today, I really couldn't find a buyer." Asad countered that secondaries changed the math: "The founders are making a lot of money along the way."
Connect with the Hosts:
Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/
Topline is more than a podcast:
Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Check us out on YouTube for the #1 video podcast for founders, operators, and investors in B2B tech: https://www.youtube.com/@TOPLINE-Media Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack
Chapters: 00:00 The Math Of AI, Deals, And Equity 02:03 SaaS Margins Were A Law Of Nature 03:24 Harvey's Margins Went To Negative 50% 04:18 Sam's 200% Growth Straw Man 05:46 Open Weight Models Aren't Harvard 14:13 Open Models Vs. Frontier Lab Economics 19:01 What Would You Spend $1M On? 30:08 Bullish Or Bearish On The AI Trade? 34:15 Walrath's Warning And A 100x Round 36:37 Secondaries Changed The Founder Math 42:35 Most Companies Never Get The Choice 47:32 Corporate M&A Is Surging 52:04 Should Equity Vest Monthly? 57:40 AJ's Case For Performance Equity 1:02:49 Bulls And Bears: AI Catastrophe
CRM As A Business World Model: The Future For GTM Teams? | Keith Peiris, CEO @ Lightfield
Keith Peiris, Co-Founder and CEO of Lightfield, joins Sam Jacobs, AJ Bruno, and Asad Zaman to talk about building an agentic CRM that launched in November 2025, has been adopted by more than 5,000 customers …
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Keith Peiris, Co-Founder and CEO of Lightfield, joins Sam Jacobs, AJ Bruno, and Asad Zaman to talk about building an agentic CRM that launched in November 2025, has been adopted by more than 5,000 customers, and just raised a $47 million Series A led by Andreessen Horowitz. Topics include why every system of record was really a forecasting tool, how to get reliable output from non-deterministic models, and the two reasons companies actually rip out Salesforce or HubSpot. Plus, a spirited debate on whether the SaaS partner ecosystem is dead, why AI-native deal sizes at 200-person companies can rival enterprise contracts, and how Lightfield landed on a mix of seat-based and consumption pricing. Key Takeaways: - Plan for models that will always make some mistakes. Keith builds Lightfield on the assumption that models stay non-deterministic, and calls reliability "a harness problem" that they're making fantastic progress against. - Use LLMs for insight and plain code for arithmetic. When Asad asked whether auditing AI forecasts saves anyone any time, Keith described a one-time implementation where Lightfield's head of finance checked every formula: "We converted some things from prompts to real code, right? I don't want LLMs doing math. I want real code doing math." That got the dashboards 95% of the way there, leaving the models to flag which deals were on the cusp because of missing features or competition. - Slightly better AI output won't justify replacing a CRM. After several rip-and-replace projects off Salesforce and HubSpot, Keith said marginally better agentic emails are "not a good enough reason to change a system of record." The two reasons that do move customers are believing one model of the business improves every stage of the revenue funnel, with SDRs pulling real-time case studies from customer success, and higher-level scenario planning, where "the modeling really matters. The data completion really matters." - Put predictable work in the seat price and meter the work with visible ROI. Lightfield tried both extremes, and pure consumption backfired: "It's like going to a store where everything's really expensive, that our customers didn't touch anything." The seat and platform fee now covers the core CRM, call recording, and the data model, while pipeline generation, AI workflow automations, and scenario planning run on consumption, because "most revenue leaders, CEOs… have an uncapped budget for business intelligence." Connect with the Hosts & Guests: Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: Keith Peiris, Co-Founder & CEO at Lightfield - https://www.linkedin.com/in/keithpeiris/ Topline is more than a Podcast: Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Check us out on YouTube for the #1 video podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slackSPOTLIGHT: What It Takes to Step into the CEO Role | Eric Anderson, CEO @ Walnut
What happens when a seasoned GTM leader becomes CEO for the first time and steps into a founder-led company with a global team? In this episode, Eric Anderson, CEO of Walnut, shares what it's really like to …
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What happens when a seasoned GTM leader becomes CEO for the first time and steps into a founder-led company with a global team?
In this episode, Eric Anderson, CEO of Walnut, shares what it's really like to take over a business built by someone else. He talks with AJ Bruno about building trust across time zones, rebuilding the go-to-market motion, and making bold decisions while honoring legacy culture.
From listening tours to tough calls on pricing and segmentation, Eric opens up about the challenges and wins of his first six months in the role.
Eric talks about: - What it's really like to step into a founder-led company as a first-time CEO - Building trust and alignment across a global, distributed leadership team - Why CEOs need to be willing to make bold and unpopular decisions - The challenge of walking away from revenue that doesn't fit the business - How pricing and market segmentation can force difficult but necessary changes - Why rebuilding the GTM organization can unlock a company's next stage of growth
Chapters
00:00 Introduction to Eric Anderson and Walnut 02:30 From GTM Leader to First-Time CEO 06:49 Leading Across Cultures and Time Zones 09:11 The Boardroom: A New CEO's Balancing Act 11:36 Why CEOs Have to Make the Hard Calls 15:00 The Cost of Trying to Serve Everyone 16:52 Rebuilding Walnut for What's Next 18:30 Where to Find Eric and Walnut Try Walnut: walnut.io
RevOps for Hypergrowth (Fireworks AI, Perplexity, Exa & More) | CEO @ Go Nimbly, Jen Igartua
Jen Igartua, CEO at Go Nimbly, joins Sam Jacobs, AJ Bruno, and Asad Zaman. Her client roster is wild: Fireworks AI, Perplexity, Exa, and Wispr Flow, plus some of the biggest names in SaaS. Topics in today's …
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Jen Igartua, CEO at Go Nimbly, joins Sam Jacobs, AJ Bruno, and Asad Zaman. Her client roster is wild: Fireworks AI, Perplexity, Exa, and Wispr Flow, plus some of the biggest names in SaaS. Topics in today's episode include how the fastest-growing AI-native companies are growing in spite of their revenue operations (not because of them), the first project she runs when she wants to show ROI fast, and how she makes the case that RevOps is a support function and always was. Plus, whether the GTM engineer is anything more than RevOps with better marketing (and more)!
Key Takeaways:
- Operational debt at the fastest-growing AI companies tracks demand, not management quality. Go Nimbly's second customer was Zendesk in 2016, where the head of IT told her "oh, we've grown in spite of our operations." Jen shares what it takes to make a difference at the breakneck pace these environments demand.
- RevOps spent a decade insisting it was strategic, and Jen thinks that cost the function credibility with the sellers it exists to serve. As she says in the episode: "I think that operators have been doing an injustice to sellers for a long time. And we are starting to really take onus of the fact that revenue operations needs to be a support function to the sales team. And we've been fighting it forever. We are not a support function. And I'm like, we actually are." Asad, who has argued the same line for years, put the failure mode in football terms: "if a goalkeeper starts trying to play like a striker, you don't let in a lot of goals, right?"
- In a people business, staffing is the product, and Jen only learned that after COVID took Go Nimbly down to 20 people. The rule she rebuilt around is "I should only take projects of skills that I want to nurture," then staff someone who is 80% of the way there so the last 20% is stretch. "Our whole job is playing Tetris with resources." She is equally direct about what did not work: "I poured a bunch of money in being tech enabled... I burned millions of dollars trying to do it," because at her clients' scale "everything's custom." The payoff line is the one to keep: "if you nail staffing, you grow a really great services organization."
Connect with the Hosts & Guests:
Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: Jen Igartua, CEO at Go Nimbly - https://www.linkedin.com/in/jen-igartua/
Topline is more than a podcast:
Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech: https://www.joinpavilion.com/topline-podcast Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack 00:00 Introducing Jen Igartua 02:15 Growing In Spite Of Their Operations 05:46 Top Of Funnel Is The First Fix 06:39 What AI-Native Ops Teams Actually Have 10:50 The Twenty-Rep Qualification Bar 11:37 Is Sales More Broken Than Before 15:00 RevOps Is A Support Function 16:29 Do Great Products Make Great Sellers 22:51 Caesars, COVID, And Twenty People 24:56 Lessons From A Services Business 28:21 Staffing Is The Whole Game 31:10 Why Contractors Do Not Work 40:09 What Is A GTM Engineer Really 49:26 What Scares Jen About 2027 54:40 Bulls and Bears
SPOTLIGHT: Skipping the SMB Trap and Building for Big Brands | Matt Allison, CEO & Founder @ Handraise
Matt Allison, CEO and Founder of Handraise, joins us to share why he's skipping the SMB trap and building an AI-powered media intelligence platform for enterprise from day one. Drawing on hard-won lessons from …
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Matt Allison, CEO and Founder of Handraise, joins us to share why he's skipping the SMB trap and building an AI-powered media intelligence platform for enterprise from day one. Drawing on hard-won lessons from scaling TrendKite, Matt breaks down how Handraise is targeting $30K+ deals with brands like Walgreens and Hershey, the importance of patience in early go-to-market, and how AI is helping them build a more thoughtful, scalable, and enterprise-ready product from the start.
Matt also talks about: - Why Handraise is skipping the SMB trap and going enterprise from day one - What TrendKite taught him about building for high-value, high-retention customers - Why patience and discipline matter when you're building an enterprise GTM motion - How AI is helping Handraise build a more sophisticated product with a lean team - Why being AI-first changes what's possible in product development - How to build a sustainable business without chasing hypergrowth at all costs Chapters: 00:00 Introduction to Matt Allison and Handraise 01:15 Why Handraise Is Going Enterprise From Day One 08:46 The Challenge: Building for $30K+ Enterprise Deals 11:56 Why Patience Matters in Enterprise GTM 15:17 How AI Is Changing Product Development 19:02 Building an AI-First, Enterprise-Ready Product 22:43 Why Handraise Isn't Chasing Hypergrowth 26:00 Matt's Favorite Book and Podcast 28:00 Where to Find Matt and Handraise Try Handraise: handraise.com
Forget Growth. Your Valuation Depends On Your AI Story | Tomasz Tunguz, GP @ Theory Ventures
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 …
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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
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 …
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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
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 …
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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 NameSPOTLIGHT: 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 …
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Bryan Murphy, CEO of Smartling, confronts a $40 billion industry stuck in the slow lane—the world of translation. Most companies still handle translations like it's 1999: manual, expensive, and painfully slow. Bryan saw AI as the game changer that could rewrite the rules, but integrating it wasn't a walk in the park.
He shares how Smartling harnessed AI to not just cut costs and speed up translation but to finally boost quality close to human-level precision without losing control over brand voice or nuance. Yet, making this leap meant upheaval: reorganizing teams, hiring AI experts, and establishing ruthless R&D discipline to separate winning ideas from distractions. Bryan also shares: - Why a $40 billion translation industry was ripe for disruption - How AI helped Smartling move from faster and cheaper to dramatically better - What it took to bring AI into a traditional business without sacrificing quality or brand voice - Why hiring the right AI talent was critical to making the shift - How ruthless R&D discipline helps separate breakthrough ideas from distractions - Why every AI initiative needs a clear connection to customer outcomes Chapters 00:00 - Introduction to Bryan Murphy and Defining the Translation Challenge 02:30 - The Hidden $40B Translation Market and Its Untapped Potential 06:00 - Early AI in Translation: Faster and Cheaper, But Not Yet Better 09:20 - Human-in-the-Loop AI: Boosting Translator Productivity Tenfold 13:00 - Unlocking Market Expansion Through Improved SEO and Digital Footprint 15:00 - The Moment of Truth: Recognizing GPT's Impact and Rolling Out Rapid Innovation 18:00 - Overcoming Organizational Challenges: From Excitement to Structured Execution 22:00 - The Discipline of "Customer-First" in AI Development and Roadmapping 24:00 - Leadership Lessons: Listening Without Losing Vision Amidst Painful Change 26:00 - Winning Customer Trust: Betting On Proofs of Concept Against Skeptics 28:00 - Personal Insights: Favorite Leadership Books and the Role of Intellectual Curiosity 33:00 - Wrap-up and Invitation to Follow Smartling's AI-Empowered Evolution Try Smartling: smartling.com
The Unwritten Rules of CRO Survival | Rick Smolen, CRO @ ShipHero
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 …
Shownotes
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
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 …
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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/
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 …
Shownotes
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
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 …
Shownotes
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.
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 …
Shownotes
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
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 …
Shownotes
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
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 …
Shownotes
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
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 …
Shownotes
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
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