Pavilion

If you like what you heard from Kyle today, make sure to <a href= "https://www.joinpavilion.com/the-revenue-leadership-podcast">follow The Revenue Leadership Podcast</a> for new episodes every Wednesday. Want more content from the Topline media family? <a href= "https://www.joinpavilion.com/topline-podcast">Listen to Topline Podcast</a> with Sam Jacobs, AJ Bruno, and Asad Zaman. <a href= "https://www.joinpavilion.com/topline-slack">Join the Topline Slack channel</a> to engage with hosts, guests, and other listeners. <a href= "https://www.joinpavilion.com/topline-newsletter">Subscribe to Topline Newsletter</a> written by Asad Zaman.

Mark Roberge on Redefining Sales Leadership in the AI Era

Eric Simons spent seven years building toward a vision that almost never saw the light of day. After countless iterations, near-misses, and growing pressure from his board to shut the company down, he and his cofounder made one final bet—and that bet became Bolt. In just four months, Bolt skyrocketed to $40 million in ARR, becoming one of the fastest-growing SaaS products in recent memory. In this episode, Eric joins the Topline team to share the full story. He explains how years of quiet technical innovation finally met a market ready for transformation, how training for an Ironman helped him build the resilience to survive the lows, and why a disciplined, capital-efficient mindset became his secret weapon through both drought and breakout. Thanks for tuning in! New episodes of Topline drop every Sunday and Thursday. Join the revenue leaders redefining growth at Pavilion's CRO Summit 2025, which will be held on June 3rd at the Denver Art Museum.<a href="https://www.joinpavilion.com/cro-summit" rel="noopener noreferrer" target="_blank"> Register today</a>. Stay ahead with the latest industry developments and emerging go-to-market trends with Topline Newsletter by Asad Zaman. <a href="https://www.joinpavilion.com/topline-newsletter" rel="noopener noreferrer" target="_blank">Subscribe today</a>. <a href="https://www.joinpavilion.com/the-revenue-leadership-podcast" rel="noopener noreferrer" target="_blank">Tune in to The Revenue Leadership Podcast</a> every Wednesday, where host Kyle Norton talks with real revenue operators and dives deep into what it takes to succeed as a modern revenue leader. You’re invited!<a href="https://www.joinpavilion.com/topline-slack" rel="noopener noreferrer" target="_blank"> Join the free Topline Slack channel</a> to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast! Key chapters:(00:00) - Introduction(01:12) - Eric Simons and the Rise of Bolt(05:42) - The Importance of Pivots in Startups(09:25) - Navigating Product Market Fit and Competition(18:25) - Maintaining Mental Resilience as an Entrepreneur(24:31) - Team Management Through Uncertainty(28:50) - The Challenges of Rapid Growth and Scaling(35:42) - Rapid Growth in the AI Era(38:01) - Bootstrapping and Calculated Bets(41:44) - Navigating Investor Pressure(44:55) - Market Signals and Product-Market Fit(49:32) - The Role of Social Media in Growth(54:41) - Sustainable Growth and Retention Strategies(01:00:12) - Learning from Competition(01:02:39) - Future Vision and Market Positioning

Eric Simons spent seven years building toward a vision that almost never saw the light of day. After countless iterations, near-misses, and growing pressure from his board to shut the company down, he and his cofounder made one final bet—and that bet became Bolt. In just four months, Bolt skyrocketed to $40 million in ARR, becoming one of the fastest-growing SaaS products in recent memory.

In this episode, Eric joins the Topline team to share the full story. He explains how years of quiet technical innovation finally met a market ready for transformation, how training for an Ironman helped him build the resilience to survive the lows, and why a disciplined, capital-efficient mindset became his secret weapon through both drought and breakout.


E111: How Bolt Hit $40M in Four Months and Why It Took Eric Simons Seven Years to Get There

How Bolt Hit $40M in Four Months and Why It Took Eric Simons Seven Years to Get There

In this episode, Yext CEO Michael Walrath joins Sam, Asad, and AJ to talk about what comes after Google. With over two decades of experience leading and investing in internet businesses—including Right Media and Moat—Michael unpacks how AI is reshaping the way we search, discover, and interact with information online. He explains why the old rules of SEO no longer apply, how structured data and digital presence are becoming mission-critical, and what brands need to do now to stay visible in an AI-first world. Michael also shares candid insights on running a public company through market whiplash, how he thinks about signal vs. noise when allocating capital, and why he’s choosing profitability over prediction. Thanks for tuning in!Join the revenue leaders redefining growth at Pavilion's CRO Summit 2025, which will be held on June 3rd at the Denver Art Museum.<a href="https://www.joinpavilion.com/cro-summit" rel="noopener noreferrer" target="_blank"> Register today</a>. <a href="https://www.joinpavilion.com/topline-slack" rel="noopener noreferrer" target="_blank">Join the free Topline Slack channel</a> to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast! <a href="https://www.joinpavilion.com/topline-newsletter" rel="noopener noreferrer" target="_blank">Subscribe to the Topline Newsletter</a> to get the latest industry developments and emerging go-to-market trends delivered to your inbox every Thursday. <a href="https://www.joinpavilion.com/the-revenue-leadership-podcast" rel="noopener noreferrer" target="_blank">Tune into The Revenue Leadership Podcast with Kyle Norton</a> every Wednesday. Kyle dives deep into the strategies and tactics that drive success for revenue leaders like Jason Lemkins of SaaStr, Stevie Case of Vanta, and Ron Gabrisko of Databricks.

In this episode, Yext CEO Michael Walrath joins Sam, Asad, and AJ to talk about what comes after Google. With over two decades of experience leading and investing in internet businesses—including Right Media and Moat—Michael unpacks how AI is reshaping the way we search, discover, and interact with information online.

He explains why the old rules of SEO no longer apply, how structured data and digital presence are becoming mission-critical, and what brands need to do now to stay visible in an AI-first world. Michael also shares candid insights on running a public company through market whiplash, how he thinks about signal vs. noise when allocating capital, and why he’s choosing profitability over prediction.

E110: How CEO Michael Walrath is building Yext for a world beyond Google

Sam Jacobs, AJ Bruno, and Asad Zaman confront the emotional weight and operational strain of leading through sustained GTM volatility. They reflect on the mental health toll of missed quarters, the pressure to perform under investor scrutiny, and the fine line between perseverance and sunk-cost thinking. The trio explores how founders can navigate uncertain markets with clear contingency planning, why Pavilion is betting big on small peer groups to improve retention, and what the recent wave of strategic M&amp;A reveals about the shifting tech landscape. Thanks for tuning in! Join the revenue leaders redefining growth at Pavilion's CRO Summit 2025, which will be held on June 3rd at the Denver Art Museum. <a href="https://www.joinpavilion.com/cro-summit" rel="noopener noreferrer" target="_blank">Register today</a>. <a href="https://www.joinpavilion.com/topline-slack" rel="noopener noreferrer" target="_blank">Join the free Topline Slack channel</a> to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast! <a href="https://www.joinpavilion.com/topline-newsletter" rel="noopener noreferrer" target="_blank">Subscribe to the Topline Newsletter</a> to get the latest industry developments and emerging go-to-market trends delivered to your inbox every Thursday. <a href="https://www.joinpavilion.com/the-revenue-leadership-podcast" rel="noopener noreferrer" target="_blank">Tune into The Revenue Leadership Podcast with Kyle Norton</a> every Wednesday. Kyle dives deep into the strategies and tactics that drive success for revenue leaders like Jason Lemkins of SaaStr, Stevie Case of Vanta, and Ron Gabrisko of Databricks. Key Moments:(00:00) Introduction and Reflections on Past Guests(02:59) The Impact of AI on Education(05:56) Market Pulse Check and Economic Outlook(08:58) Navigating Challenges as Founders(11:55) Mental Health and Resilience in Business(15:04) Investor Pressures and Market Dynamics(17:48) The Importance of Adaptability in Entrepreneurship(20:59) Learning from Failure and Moving Forward(33:53) Revenue Growth and Business Optionality(34:56) Leadership Accountability and Personal Growth(36:24) Compassionate Leadership in Business(38:01) Optimism vs. Realism in Business(39:31) Market Trends and Business Strategy(42:04) Building Community and Crafting Business Assets(43:41) Market Dependency and Business Performance(46:47) The Importance of Team Building(47:15) M&amp;A Activity and Market Dynamics

Sam Jacobs, AJ Bruno, and Asad Zaman confront the emotional weight and operational strain of leading through sustained GTM volatility. They reflect on the mental health toll of missed quarters, the pressure to perform under investor scrutiny, and the fine line between perseverance and sunk-cost thinking. The trio explores how founders can navigate uncertain markets with clear contingency planning, why Pavilion is betting big on small peer groups to improve retention, and what the recent wave of strategic M&amp;A reveals about the shifting tech landscape.

E109: Burnout, Breakthroughs & the New Reality of GTM Leadership

E109: Burnout, Breakdowns & the Will to Keep Building

When <a href="https://www.linkedin.com/in/samfjacobs/" rel="noopener noreferrer" target="_blank">Sam Jacobs</a> founded Pavilion, formerly Revenue Collective, he set out to build a private community for operators in a startup world that traditionally celebrated only founders and operators. But after the community grew rapidly, now totaling 10,000+ members, questions arose about whether the once-exclusive membership had become too open. In this special Topline Spotlight episode, Sam joins co-hosts AJ Bruno and Asad Zaman to discuss how rapid expansion diluted the community’s focus, what it took to course-correct, and why building something great takes time—and restraint. You're invited! <a href="https://www.joinpavilion.com/topline-slack" rel="noopener noreferrer" target="_blank">Join the free Topline Slack channel</a> to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast! <a href="https://www.joinpavilion.com/topline-newsletter" rel="noopener noreferrer" target="_blank">Subscribe to the Topline Newsletter</a> to get the latest industry developments and emerging go-to-market trends delivered to your inbox every Thursday. <a href="https://www.joinpavilion.com/the-revenue-leadership-podcast" rel="noopener noreferrer" target="_blank">Tune into The Revenue Leadership Podcast with Kyle Norton</a> every Wednesday. Kyle dives deep into the strategies and tactics that drive success for revenue leaders like Jason Lemkins of SaaStr, Stevie Case of Vanta, and Ron Gabrisko of Databricks. Key Moments:(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

SPOTLIGHT: How CEO Sam Jacobs Is Redefining Pavilion’s Identity

In this episode, Sam, AJ, and Asad are joined by <a href="https://www.linkedin.com/in/rubinguy/" rel="noopener noreferrer" target="_blank">Guy Rubin</a> to dive deep into the critical insights from <a href="https://www.joinpavilion.com/resource/2025-gtm-benchmarks-ebsta-pavilion" rel="noopener noreferrer" target="_blank">Ebsta's latest sales benchmarking report</a>. Their report uncovers what separates high-performing sales organizations from the rest. They take a sobering look at current quota attainment trends and why most teams continue to fall short of targets. They also explore how leadership decisions create ripple effects across sales performance, examining the structural and cultural factors driving results. This episode delivers actionable takeaways for sales leaders looking to improve quota attainment, optimize their tech stack, and build more resilient teams in an increasingly complex selling environment. Thanks for tuning in! Join the revenue leaders redefining growth at Pavilion's CRO Summit 2025, which will be held on June 3rd at the Denver Art Museum. <a href="https://www.joinpavilion.com/cro-summit" rel="noopener noreferrer" target="_blank">Register today</a>. <a href="https://www.joinpavilion.com/topline-slack" rel="noopener noreferrer" target="_blank">Join the free Topline Slack channel</a> to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast! <a href="https://www.joinpavilion.com/topline-newsletter" rel="noopener noreferrer" target="_blank">Subscribe to the Topline Newsletter</a> to get the latest industry developments and emerging go-to-market trends delivered to your inbox every Thursday. <a href="https://www.joinpavilion.com/the-revenue-leadership-podcast" rel="noopener noreferrer" target="_blank">Tune into The Revenue Leadership Podcast with Kyle Norton</a> every Wednesday. Kyle dives deep into the strategies and tactics that drive success for revenue leaders like Jason Lemkins of SaaStr, Stevie Case of Vanta, and Ron Gabrisko of Databricks. Key Moments: (00:00) Introduction(03:00) Sales Quota Attainment and Market Dynamics(06:00) The Role of Leadership in Sales Success(08:49) Data-Driven Sales Strategies(11:58) The Challenge of Sales Performance(15:03) The Future of Sales Talent and AI's Impact(17:54) Concentration of Talent in Sales Organizations(22:49) The Concentration of Talent in Organizations(23:41) Data-Driven Insights for Sales Success(25:50) The Role of AI in Sales(26:41) The Myth of the A Player(28:49) The Importance of Consistency in Sales Processes(30:01) The Shift to Full Cycle Sales(32:21) Customer Relationship Management in Sales(34:41) The Impact of Leadership on Sales Performance(37:53) Navigating Volatility in Sales(40:54) Building a Data-Driven Sales Organization(48:05) Pop Culture References and Team Dynamics(49:14) Market Dynamics and Leadership Changes(50:44) Founder Friendliness and CEO Replacement(54:14) The Role of Founders vs. Non-Founder CEOs(01:00:20) Community and Personal Growth(01:01:30) Inspiring Media Ventures and Closing Thoughts

E108: Unpacking Ebsta’s Benchmarking Report with Guy Rubin

When Rick Smolen stepped into the CRO role at ShipHero, he wasn’t just inheriting a sales team—he was taking on the entire customer lifecycle. From marketing to partnerships to customer success, Rick had to quickly learn how to lead teams in functions he’d never directly owned before. In this episode, he shares what that transition was really like, the mistakes he made early on, and how curiosity became his most powerful leadership tool. You're invited! <a href="https://www.joinpavilion.com/topline-slack" rel="noopener noreferrer" target="_blank">Join the free Topline Slack channel</a> to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast! <a href="https://www.joinpavilion.com/topline-newsletter" rel="noopener noreferrer" target="_blank">Subscribe to the Topline Newsletter</a> to get the latest industry developments and emerging go-to-market trends delivered to your inbox every Thursday. <a href="https://www.joinpavilion.com/the-revenue-leadership-podcast" rel="noopener noreferrer" target="_blank">Tune into The Revenue Leadership Podcast with Kyle Norton</a> every Wednesday. Kyle dives deep into the strategies and tactics that drive success for revenue leaders like Jason Lemkins of SaaStr, Stevie Case of Vanta, and Ron Gabrisko of Databricks. Key Moments: (00:00) Introduction(01:10) Overview of ShipHero and its services(03:15) Rick's career Journey(06:37) Challenges of transitioning to CRO(09:36) Curiosity and leadership dynamics(14:27) Building a leadership team and embracing failure(18:12) Evaluating leadership success(22:59) Key takeaways and book recommendations

When Rick Smolen stepped into the CRO role at ShipHero, he wasn’t just inheriting a sales team—he was taking on the entire customer lifecycle. From marketing to partnerships to customer success, Rick had to quickly learn how to lead teams in functions he’d never directly owned before. In this episode, he shares what that transition was really like, the mistakes he made early on, and how curiosity became his most powerful leadership tool.

SPOTLIGHT: How Rick Smolen Built Confidence Leading Outside of Sales

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.

Pavilion

Mark Roberge on Redefining Sales Leadership in the AI Era

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