The GitLab way: Kindness, transparency, and short toes | David DeSanto (CPO‪)‬ Lenny's Podcast: Product | Growth | Career

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
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Find the transcript at: https://www.lennysnewsletter.com/p/the-gitlab-way
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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
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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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
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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