E28: Interns to Enterprise: How Cresta’s CRO Built a Category Leader

Listen to this episode from The Revenue Leadership Podcast with Kyle Norton on Spotify. What does it take to go from zero to your first enterprise customer? For Cresta, it meant their CEO and CTO becoming interns at Intuit—and their engineering team living in an Airbnb next to the call center they were trying to disrupt. In this episode, Kyle talks with Alex Cramer, CRO of Cresta, about the unglamorous grind of cold-starting in enterprise, why today’s deals demand more consensus (and skill) than ever, and how to scale a team when every deal feels like a bespoke knife fight. Plus, Alex’s hardest-won lessons—from equity pitfalls to why endurance separates good CROs from great ones. New episodes of The Revenue Leadership Podcast with Kyle Norton drop every Wednesday. Want more from Topline? Tune into the Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Catch full-length episodes every Sunday and bite-sized mini-episodes every Thursday, where our hosts sit down with top B2B tech leaders to unpack their biggest challenges—and how they overcame them. And don't forget to 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.