E108: Unpacking Ebsta’s Benchmarking Report with Guy Rubin
In this episode, Sam, AJ, and Asad are joined by Guy Rubin to dive deep into the critical insights from Ebsta's latest sales benchmarking report. 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. Register today.Join the free Topline Slack channel to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast!Subscribe to the Topline Newsletter to get the latest industry developments and emerging go-to-market trends delivered to your inbox every Thursday.Tune into The Revenue Leadership Podcast with Kyle Norton 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
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1:08:18
SPOTLIGHT: How Rick Smolen Built Confidence Leading Outside of Sales
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! Join the free Topline Slack channel to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast!Subscribe to the Topline Newsletter to get the latest industry developments and emerging go-to-market trends delivered to your inbox every Thursday.Tune into The Revenue Leadership Podcast with Kyle Norton 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
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26:08
E107: Scaling ClickUp to 10M+ Users with COO Gaurav Agarwal
In this episode, we’re joined by Gaurav Agarwal, COO of ClickUp, who’s led the company’s explosive growth to over 10 million users while slashing CAC by 3X and achieving profitability. Gaurav dives into why ClickUp’s hybrid motion is crushing it and how to align both for compounding returns, how they reduced CAC by ruthlessly optimizing spend and embracing incrementality over attribution, how to build teams that thrive under high accountability, and more.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. Register today.Join the free Topline Slack channel to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast!Subscribe to the Topline Newsletter to get the latest industry developments and emerging go-to-market trends delivered to your inbox every Thursday.Tune into The Revenue Leadership Podcast with Kyle Norton 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 to Gaurav Agarwal and ClickUp(02:54) Gaurav's Journey from Banking to Startups(06:04) Growth Strategies and Challenges at ClickUp(14:54) Branding vs. Performance Marketing in SaaS(21:54) Navigating Brand Marketing and Measurement(24:44) The Importance of Self-Awareness in Leadership(27:39) The Role of Pain in Leadership and Growth(35:57) The Dichotomy of Being Liked vs. Respected(40:39) Building Resilient Teams Through Real Challenges(51:14) The Dynamics of PLG and SLG(52:37) Fragmentation in Go-to-Market Strategies(56:42) The Role of Marketing in Revenue Generation(01:00:45) Influences and Inspirations in Business
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1:11:33
SPOTLIGHT: Untangling Tech Debt and Finding Product-Market Fit with Russ Mikowski of SurePeople
Russ Mikowski, CEO of SurePeople and longtime revenue leader intech, never planned to become a CEO, until he was recruited to transform a 10-year-old company grappling with technical debt, a scattered ICP, and untapped potential. In this episode of Topline Spotlight, Russ opens up about the tough decisions he’s made since taking the helm: rebuilding instead of refactoring, saying "no" to legacy customers, and doubling down on a focused go-to-market strategy for SurePeople’s innovative psychometric assessment platform, Prism.You're invited! Join the free Topline Slack channel to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast!Subscribe to the Topline Newsletter to get the latest industry developments and emerging go-to-market trends delivered to your inbox every Thursday.Tune into The Revenue Leadership Podcast with Kyle Norton 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 to Topline Spotlight(03:00) Understanding SurePeople and Its Mission(05:51) Russ's Journey to CEO and Company History(08:55) Navigating Technical Debt and Product Development(12:01) Defining Ideal Customer Profile (ICP) and Market Focus(14:50) Company Culture and Communication Strategies(17:53) Inspiration and Leadership Philosophy
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26:54
E106: AI-Driven vs AI-First vs AI-Native with Eric Wolford of Accel
In this episode, Sam Jacobs and Asad Zaman are joined by Eric Wilford, a venture partner at Accel, to discuss venture investing with a focus on AI-first companies. The discussion delves into what defines an AI-first company, the implications of AI on product development and go-to-market strategies, and the influence of macroeconomic conditions on venture investments. Eric also shares his perspectives on valuation, the competitive dynamics in AI, and the role of authenticity in successful entrepreneurship.Thanks for tuning in! Join the free Topline Slack channel to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast!Subscribe to the Topline Newsletter to get the latest industry developments and emerging go-to-market trends delivered to your inbox every Thursday.Tune into The Revenue Leadership Podcast with Kyle Norton 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(03:21) - Discussion on AI-First Companies(06:35) - AI in Enterprise SaaS and Product Customization(18:00) - Macro Economy and Venture Investing(22:23) - Navigating Recessions and AI Era(25:05) - Valuations in the AI Market(30:58) - Raising Capital: Strategies and Debates(35:57) - Founders' Goals and Investor Alignment(38:53) - Inspiration and Final Thoughts
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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