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

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Find the transcript at: www.lennysnewsletter.com

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Where to find David DeSanto:

• X: twitter.com

• LinkedIn: www.linkedin.com

• Threads: www.threads.net

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Where to find Lenny:

• Newsletter: www.lennysnewsletter.com

• X: twitter.com

• LinkedIn: www.linkedin.com

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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: about.gitlab.com

• UX Showcase—David DeSanto introduction to UX team and AMA: www.youtube.com

• The GitLab Handbook: handbook.gitlab.com

• Sid Sijbrandij on LinkedIn: www.linkedin.com

• Y Combinator: www.ycombinator.com

• GitLab issues: docs.gitlab.com

• Salesforce: www.salesforce.com

• GitLab values: handbook.gitlab.com

• GitLab organizational structure: handbook.gitlab.com

• GitLab direction: about.gitlab.com

• Dogfooding: A simple practice to help you build better products: medium.com

• The ultimate guide to adding a PLG motion | Hila Qu (Reforge, GitLab): www.lennysnewsletter.com

• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): www.lennysnewsletter.com

• HubSpot: www.hubspot.com

• Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: www.amazon.com

• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: www.lennyspodcast.com

• Open-core model: en.wikipedia.org

• GitLab Duo: about.gitlab.com

• GitLab Docs: docs.gitlab.com

• Anthropic: www.anthropic.com

• GitLab Acquires UnReview to Expand Its DevOps Platform with Machine Learning Capabilities: about.gitlab.com

• Essentialism: The Disciplined Pursuit of Less: www.amazon.com

• The Mission Critical Core/Context Model for Product Managers: secretpmhandbook.com

• The Devil’s Hour on AppleTV+: tv.apple.com

• Glass Onion: A Knives Out Mystery on Netflix: www.netflix.com

• Taylor Swift’s The Eras Tour on Prime Video: www.amazon.com

• The STAR method: capd.mit.edu

• Artifact News: artifact.news

• Superhuman: superhuman.com

• Arc browser: arc.net

• An inside look at how The Browser Company builds product: www.lennysnewsletter.com

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Production and marketing by penname.co. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.