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

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-market/ • Open-core model: https://en.wikipedia.org/wiki/Open-core_model • GitLab Duo: https://about.gitlab.com/gitlab-duo/ • GitLab Docs: https://docs.gitlab.com/ • Anthropic: https://www.anthropic.com/ • GitLab Acquires UnReview to Expand Its DevOps Platform with Machine Learning Capabilities: https://about.gitlab.com/press/releases/2021-06-02-gitlab-acquires-unreview-machine-learning-capabilities/ • Essentialism: The Disciplined Pursuit of Less : https://www.amazon.com/Essentialism-Disciplined-Pursuit-Greg-McKeown/dp/0804137382 • The Mission Critical Core/Context Model for Product Managers: https://secretpmhandbook.com/the-mission-critical-corecontext-model-for-product-managers/ • The Devil’s Hour on AppleTV+: https://tv.apple.com/us/show/the-devils-hour/umc.cmc.3zw4tyzd4lvor5mwhujms63x3 • Glass Onion: A Knives Out Mystery on Netflix: https://www.netflix.com/title/81458416 • Taylor Swift’s The Eras Tour on Prime Video: https://www.amazon.com/TAYLOR-SWIFT-ERAS-EXTENDED-VERSION/dp/B0CP99SN2B • The STAR method: https://capd.mit.edu/resources/the-star-method-for-behavioral-interviews/ • Artifact News: https://artifact.news/ • Superhuman: https://superhuman.com/ • Arc browser: https://arc.net/ • An inside look at how The Browser Company builds product: https://www.lennysnewsletter.com/p/competing-with-giants-an-inside-look — Production and marketing by https://penname.co/ . For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com . — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe