The GitLab way: Kindness, transparency, and short toes | David DeSanto (CPO)

(instrumental music) You guys share so many of the things that most people keep secret. You post videos of your team meetings on YouTube.

We get people who then contribute because of what they see. "Oh, I can go build that, I know what that is." "Hey, I ran into that same problem too, (laughs) I'd love to hear how you solved it."

You also have this handbook, how you onboard people, how (laughs) account payables works at Gitlab.

We'll have companies who will fork the handbook. If you can leverage what Gitlab has done, that's amazing.

You mentioned the value of short toes, which I was definitely gonna ask about. (laughs)

That's where if you have long toes, you feel like people are stepping on you. Whereas if you have short toes, it's about the work, it's not about you. You end with a lot less of the negative head-butting, especially in an asynchronous culture like Gitlab.

Is there any tips you could share with PMs that are just struggling in a remote world?

If everyone's really annoyed at you, you're probably actually doing your job well.

Today, my guest is David Di Santo. David is the chief product officer at Gitlab, which is an incredibly unique company. It's the largest remote only company in the world. They share many of their team meetings on YouTube, and they've grown from being just a source code management business competing with GitHub, to a multi-product platform that covers security, compliance, continuous integration, project management, deploy tools and more. Many of which are infused with AI magic. In our conversation, we dig into Gitlab's culture of transparency, including how they operationalize it, what they share publicly versus what they don't, the surprising benefits of working this way, and why it's worth considering going transparent with your organization. Also, we explore some of Gitlab's other unique cultural values, like kindness and having short toes. Plus, David shares a bunch of great advice for scaling remote work based on what's worked well at Gitlab over the years, also when it makes sense to go breadth over depth versus depth over breadth when launching new product lines and how it worked for Gitlab over the years. This was a fascinating conversation, and if you want to learn more about a company that's doing things very differently while also kicking a lot of ass, this episode is for you. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes and it helps the podcast tremendously. With that, I bring you David Di Santo after a short word from our sponsors. This episode is brought to you by Orb. As a business, you care about revenue. But as a product team, the last thing you want to do is delay a product launch or a pricing change because your team has to rebuild billing from scratch. Orb is a flexible usage-based billing engine that lets you evolve your pricing with ease. The fastest growing product teams at companies like Vercel and Replit trust Orb to power their pricing changes and launches. Use Orb to ship product faster, stop worrying about billing, and evolve pricing with ease and control. Check it out at withorb.com/lenny and skip the line for a demo or sandbox by using promo code Lenny. That's withorb.com/lenny. This episode is brought to you by Eppo. Eppo is a next generation A/B testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp, and DraftKings rely on Eppo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features, and Eppo helps you increase experimentation velocity while unlocking rigorous deep analysis in a way that no other commercial tool does. When I was at Airbnb, one of the things that I loved most was our experimentation platform, where I could set up experiments easily, troubleshoot issues, and analyze performance all on my own. Eppo does all that and more with advanced statistical methods that can help you shave weeks off experiment time, an accessible UI for diving deeper into performance, and out-of-the-box reporting that helps you avoid annoying prolonged analytic cycles. Eppo also makes it easy for you to share experiment insights with your team, sparking new ideas for the A/B testing flywheel. Eppo powers experimentation across every use case, including product, growth, machine learning, monetization, and email marketing. Check out Eppo at geteppo.com/lenny and 10X your experiment velocity. That's geteppo.com/lenny. David, thank you so much for being here, and welcome to the podcast.