Selling to Enterprise

This week Adam is joined by Scott Johnston, CEO of Docker. Scott shares his journey to the CEO role, how he’s leading the company to not only grow revenue, but to also invest in developer facing features, their shift from a enterprise sales focus to a PLG driven model, and we even talk about Docker Desktop, the competition it faces, and the struggle they face when considering making it open source.

This week Adam is joined by Michael Grinich, Founder & CEO at WorkOS. Michael shares his journey to build WorkOS, what it takes to cross the Enterprise Chasm, and how he’s building his sales organization for growth.

This week Adam is joined by Alex Gallego, Founder & CEO at Redpanda Data, to share his builder journey to create the Redpanda streaming data platform.

This week Adam is joined by Jori Lallo, Co-founder of Linear, to talk about creating magical software and building high-quality software teams.

This week Adam is taking the show off the beaten path to speak with Adam Miller, the founder and CEO of Revel Bikes. Yes that’s right, this episode features a founder of a bike brand, not a tech brand. Adam Miller’s journey to create Revel Bikes is paved with many ups and many downs, a failed partnership, super scrappy weeks and months traveling the world to find the best manufacturing partners, the latest innovations in suspension tech and modern geometry to hit the mountain biking scene, a strong team that’s been with him every step of the way (many of which are as close as family), and truly some of the best premium bikes available on the market today. BTW, Adam (host) is an owner of a Revel bike — he has a T1000 colorway Rascal that he’s ridden on downhill trails, all-day epics, and everything in-between. If you enjoy this episode, please us know in the comments.

This week Adam is joined by Robert Ross founder and CEO of FireHydrant — the glue layer between your tech stack and your teams to mitigate and resolve incidents at scale. Robert shares his journey to become a software engineer, his time at DigitalOcean, this idea of incident management as a platform and how he shifted his focus from creating courses on incident management to recognizing the value of the software he was creating for the course — what is now known as FireHydrant. We also talk through his first experience in raising capital, what happens when the bar is raised on the reliability of the world’s software, and why their mantra is “Hire great people, who build, sell and market a great product, and you’ll have a great company.”

Adam was invited by our friends at Square to interview Jack Dorsey as part of their annual developer conference called Square Unboxed. Jack Dorsey is one of the most prolific CEOs out there — he’s a hacker turned CEO and is often working at the very edge of what’s to come (at scale). Jack is focused on what the future has to offer, he’s considered an innovator by many. He’s also a Bitcoin maximalist and has positioned himself and Block long on Bitcoin. What you’re about to hear is the fireside chat Adam had with Jack at Square Unboxed 2022. Jack and Adam discuss the vision Square has for the developer platform and why it’s so central to the company’s strategy.

Connor Sears, founder and CEO of Rewatch, joins Adam to share the journey of creating Rewatch. What began inside of GitHub to help them thrive and connect is now available to every product team on the planet. Rewatch lets teams save, manage, and search all their video content so they can collaborate async and with greater flexibility. We talk about where the tool’s inspiration came from (spoiler alert, inside GitHub it was called GitHub TV which you’ll hear during the show), how teams leverage video to reduce the constraints of communication, how Connor and his co-founder knew they had product-fit and how they grew the team and product, and of course the flip side of that — we talk about some of Connor’s failures along the way, and knowing when it’s the right time to take a big swing.

This week Sid Sijbrandij, Co-founder and CEO of GitLab, is back talking with Adam about all the details of their massive IPO last October 2021. To set the stage, this episode was recorded on Feb 1, 2022. During the show Adam mentioned they IPO’d at a $13B market cap, but they actually ended their opening day at approximately $15B. That’s a massive win for open source, GitLab, Sid, and the rest of the team. For loyal listeners you know we’ve had Sid on this show before, so of course we had to get him back on the show post-IPO to get all the details of this new journey.

This week Peer Richelsen, Co-Founder and Co-CEO of Cal.com, joins the show to talk about building the “Stripe for Time” — with a grand mission to connect a billion people by 2031 through calendar scheduling. Cal has grown from an open-source side project to one of the fastest-growing commercial open source companies. We get into all the details — what it means to be an open source Calendly alternative, how they quantify connecting a Billion people by 2031, where there’s room for innovation in the scheduling space, and why being community first is part of their secret sauce.