In this Second Acts episode, WP Engine’s (previously: ITWatchDogs’ and SmartBear’s) founder, Jason Cohen joins Krish to discuss: how predictability becomes required to withstand the pressures of scale, how Jason has consistently sought different roles (from CEO to CTO to Chief Innovation Officer) to contribute as a founder, how WP Engine set up all functions anew for the enterprise segment save for one (and how they’ve followed a similar path with other second acts), and other well-examined insights from 24 years of building B2B software.Jason: “We didn't layer on an enterprise business until four years in. And when we did, one of the things we did is we had entire teams devoted only to it. We had whole sales teams only for enterprise… And one of the nice things about us is we didn't need different engineering teams, because the same product is what people buy. So we didn't need a separate engineering team. That's part of why it made sense for us to do it. It was a different go-to-market, but not a different product. That's part of why it made sense to do it. But what we didn't do is just put on the website, ‘we [sell] to the enterprise, and that's it.”— Chapters: (03:20) The post-PMF, everything-demands-predictability mode(09:29) The external CEO as a “late-joining co-founder”(11:53) How Jason’s role has evolved across the 14 years of WP Engine(13:09) The (whole) org design puzzle(18:58) Scaling cross-team prioritization with planned debates(27:10) How WP Engine layered on an enterprise bet(28:26) A framework for approaching potential adjacencies (and second acts)(35:54) WP Engine’s practical — “map, not the terrain” — competitive strategy(46:44) Operationally living up to the one defining truth of strategy— Mentioned/Resources:WP Engine passes $100M in revenue and secures $250M investment from Silver LakeThe fundamental forces of scaleLetter to Customers – Founder/CEOWhat is the argument for staying with SMB while going up-market?What makes a strategy great— Connect with Jason:A Smart BearXLinkedIn— Connect with Krish:XLinkedIn—Chargebee is a revenue growth management platform that helps thousands of subscription businesses unlock second acts of scale with transformative billing, monetization, and retention infra. Learn more.

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