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 [email protected].—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

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