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: lennysnewsletter.com/p/the-gitl… — Where to find David DeSanto: • X: twitter.com/david_desanto • LinkedIn: linkedin.com/in/ddesanto • Threads: threads.net/@david.the.beard — Where to find Lenny: • Newsletter: lennysnewsletter.com • X: twitter.com/lennysan • LinkedIn: — In this episode, we cover: — Referenced: • GitLab: • UX Showcase—David DeSanto introduction to UX team and AMA: • The GitLab Handbook: • Sid Sijbrandij on LinkedIn: • Y Combinator: • GitLab issues: • Salesforce: • GitLab values: • GitLab organizational structure: • GitLab direction: • Dogfooding: A simple practice to help you build better products: • The ultimate guide to adding a PLG motion | Hila Qu (Reforge, GitLab): • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): • HubSpot: • Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: • Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: • Open-core model: • GitLab Duo: • GitLab Docs: • Anthropic: • GitLab Acquires UnReview to Expand Its DevOps Platform with Machine Learning Capabilities: • Essentialism: The Disciplined Pursuit of Less: • The Mission Critical Core/Context Model for Product Managers: • The Devil’s Hour on AppleTV+: • Glass Onion: A Knives Out Mystery on Netflix: • Taylor Swift’s The Eras Tour on Prime Video: • The STAR method: • Artifact News: • Superhuman: • Arc browser: • An inside look at how The Browser Company builds product: — Production and marketing by . For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed.