David DeSanto is the chief product officer of GitLab, which is the largest remote-only company in the world. They share many of their team meetings on YouTube, and they’ve grown from being an open-source code management product competing with GitHub to a multi-product platform that covers security, compliance, continuous integration, project management, and deployment tools, many of which are infused with AI magic. In our conversation, we discuss: • How GitLab operationalizes transparency • The philosophy behind recording and sharing team meetings on YouTube • Their extensive public employee handbook • GitLab’s core value of having “short toes” • Challenges and advice for doing remote work well • Strategies for ensuring effective communication in a remote work environment • GitLab’s breadth-over-depth strategy • The company’s unique approach to AI • The value of using humor in high-stakes conversations — Brought to you by: • Orb—The flexible billing engine for modern pricing • Eppo—Run reliable, impactful experiments • Paragon—Ship every SaaS integration your customers want — Find the transcript at: https://www.lennysnewsletter.com/p/the-gitlab-way — Where to find David DeSanto: • X: https://twitter.com/david_desanto • LinkedIn: https://www.linkedin.com/in/ddesanto/ • Threads: https://www.threads.net/@david.the.beard — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) David’s background (04:20) Maintaining an epic beard (05:29) Why GitLab publicly shares team meetings (09:49) The GitLab Handbook (11:30) GitLab’s issue tracker (14:29) How to successfully build a culture of transparency (18:11) Benefits of operating with transparency (19:55) The value of building in public (21:53) How GitLab implements their core value of kindness (25:16) What it means to have “short toes” (27:41) Other core values (32:16) Common reasons for not fitting in at GitLab (34:42) Advice for remote teams (42:04) Advice for getting into product (43:52) Advice for PMs who are struggling in a remote world (48:25) Specific tools that help with remote work (53:13) Time zones and remote work (57:18) Breadth-over-depth strategy (01:04:14) AI at GitLab (01:13:11) GitLab’s products and solutions (01:14:54) Lightning round — Referenced: • GitLab: https://about.gitlab.com/ • UX Showcase—David DeSanto introduction to UX team and AMA: https://www.youtube.com/watch?v=fEdsmnVKNj4 • The GitLab Handbook: https://handbook.gitlab.com/ • Sid Sijbrandij on LinkedIn: https://www.linkedin.com/in/sijbrandij/ • Y Combinator: https://www.ycombinator.com/ • GitLab issues: https://docs.gitlab.com/ee/user/project/issues/ • Salesforce: https://www.salesforce.com/ • GitLab values: https://handbook.gitlab.com/handbook/values • GitLab organizational structure: https://handbook.gitlab.com/handbook/company/structure • GitLab direction: https://about.gitlab.com/direction/ • Dogfooding: A simple practice to help you build better products: https://medium.com/agileinsider/dogfooding-a-simple-practice-to-help-you-build-better-products-b5954af4d5f7 • The ultimate guide to adding a PLG motion | Hila Qu (Reforge, GitLab): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-adding-a-plg • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building • HubSpot: https://www.hubspot.com/ • Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986 • Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennyspodcast.com/geoffrey-moore-on-finding-your-beachhead-crossing-the-chasm-and-dominating-a-mar