Topline

Pavilion
  • 4.8 (57)
  • Technology
  • Updated Weekly

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

  1. 3d ago

    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 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

    The Man Who Led 100+ CROs (Even OpenAI's) | John McMahon - 5x Post-IPO CRO / The GOAT

  2. 5d ago

    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 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

  3. Oct 18

    $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 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

    $682M Public CEO: "The Magic of 80% Gross Margin" | CEO @ Yext, Michael Walrath

  4. Oct 15

    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 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

  5. Oct 11

    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 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

    AI Revenue Is Real. But Will It Last? | Amy Konary, Founder & Chair, Subscribed Institute @ Zuora

  6. Oct 8

    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 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

  7. Oct 4

    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 once seats stop making sense. Topics include why every SaaS company needs its own agents before someone else's run on its MCP layer, why a token is the wrong unit of value, and the itemized phone bill every agent builder owes its buyers. Plus, why fixed-price deals win logos but stall expansion, the case for 40% to 60% gross margins in the agent era, and what Satya Nadella told Manny in a green room. Key Takeaways: - Price the work your agent does, not the seats it fills. In SaaS you sell 100 seats, procurement sees 20 in heavy use, and the renewal shrinks to 50. With agents, "if you've sold 100 seats and only 2 were hyper-users, you don't care because you're charging for all the uses and all the value those 2 seats were getting." For now that pricing lives between effort and output, because true outcome pricing needs attribution, and as Manny put it, "Attribution is really hard." - Make the bill readable before you argue about ROI. Manny compares it to the old itemized phone bill, where you went straight to the biggest line and asked, "Did I really call Pakistan from New York?" Tokens can't play that role: "A token should not be a unit of value for charging because a token is really kind of like the inside secret." Show the buyer the research, deck, or analysis the agent produced, because "explainability is like the first rung in the ladder." - Fixed pricing is easy money that boxes you in at renewal. Enterprises are buying one of each right now, so "new logo is not hard. Expansion is hard." Teams that land logos on fixed price hit the first renewal with nowhere to go, which is why Paid opens with a monetization consultant and takes a percentage of revenue: "You grow, I grow." - Plan for thinner margins and narrower markets. Manny learned Amazon's margins cold (books 20%, electronics 7%, jewelry 3%) and calls SaaS's 70 to 80% an anomaly of cheap money: "I feel like a normal, you know, software business will be running on 40% margins, 60% tops." Connect with the Hosts & Guests:   Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/ Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/ Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/ Guest: Manny Medina, Co-Founder & CEO at Paid - https://www.linkedin.com/in/medinism/   Topline is more than a podcast:   Subscribe to Topline Newsletter: https://toplinemedia.substack.com/ Check us out on YouTube for the #1 video podcast for founders, operators, and investors in B2B tech: https://www.youtube.com/@TOPLINE-Media Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast: https://www.joinpavilion.com/topline-slack   Chapters: 00:00 Introducing Manny Medina 01:37 What Paid Is Building 04:38 Will All Software Go Agentic? 06:35 The 100-Seat Renewal Problem 10:02 An Itemized Phone Bill for Agents 13:33 Why Outcome Pricing Takes Time 19:04 Open Source vs. Frontier Models 26:41 Pricing Agents Is an NRR Problem 33:11 Why Manny Won't Build Workflows 35:39 Fundraising Lessons From Outreach 41:10 Life Is Path Dependent 45:46 Culture Is the Exhaust of Winning 47:50 Is AI Spend Still Experimental? 58:22 The End of 80% Software Margins

    Turning AI Tokens Into ROI (That You Can Measure) | CEO @ Paid, Manny Medina

  8. Oct 1

    SPOTLIGHT: 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 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

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4.8
out of 5
57 Ratings

About

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

Information

  • Creator
    Pavilion
  • Years Active
    2023 - 2026
  • Episodes
    280
  • Rating
    Explicit
  • Copyright
    © 012671
  • Show Website
    Topline

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