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: https://www.withorb.com/lenny • Eppo—Run reliable, impactful experiments: https://www.geteppo.com/ • Paragon—Ship every SaaS integration your customers want: https://www.useparagon.com/lenny Find the transcript and references 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 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.

Lenny RachitskyhostDavid DeSantoguest

Apr 13, 20241h 21mWatch on YouTube ↗

WHAT IT’S REALLY ABOUT

Inside GitLab: Radical transparency, remote culture, and product at scale

GitLab CPO David DeSanto discusses how GitLab operationalizes extreme transparency through public meeting recordings, an open handbook, and a public issue tracker, and how this fuels community contribution and customer trust.
He explains GitLab’s cultural values—kindness, short toes, assuming positive intent, and results-focus—and how they enable a fully remote, async-first company of 2,000+ people to function effectively across 60+ countries.
DeSanto shares practical guidance on making remote work succeed (outcomes over hours, overcommunication, clear written requirements, and periodic in‑person time), plus how GitLab evolved from breadth-over-depth product strategy to deepening key areas of its DevSecOps platform.
He also outlines GitLab’s AI principles—full lifecycle coverage, privacy-first, and using the right model for each use case—and how GitLab Duo aims to materially increase productivity without compromising customers’ intellectual property.

IDEAS WORTH REMEMBERING

5 ideas

Transparency can be an execution advantage, not a competitive risk.

By publicly sharing team meetings, their handbook, roadmap, and issue tracker, GitLab attracts community contributions, builds trust with customers, and reduces internal silos—while relying on fast execution (12 releases a year for 12+ years) as the real moat.

Codified values are essential for making remote and transparency work.

Values like kindness, assuming positive intent, short toes (not personalizing feedback), and “negative feedback is one-on-one” reduce conflict and misinterpretation in an async, text-heavy environment and make high transparency psychologically sustainable.

Remote success requires clear writing, overcommunication, and async-first habits.

GitLab expects PMs to write crisp requirements, use issues as the single source of truth, document decisions in the handbook, default to async communication, and only escalate to meetings (e.g., Zoom) when written back-and-forth stalls.

Focus on outcomes and adoption, not tasks and hours.

Instead of measuring success by features shipped or bugs closed, GitLab encourages outcome metrics (e.g., percentage of customers using a feature) and sees “celebrate adoption, not shipping” as key to both remote management and better product decisions.

Use breadth-over-depth early to find your platform edges, then go deep where it matters.

GitLab initially expanded broadly across the DevSecOps lifecycle to discover where it could truly differentiate, then pivoted to depth in core areas like SCM, CI/CD, security, planning, and AI, letting adjacent areas benefit from the platform halo.

WORDS WORTH SAVING

5 quotes

If everyone's really annoyed at you, you're probably actually doing your job well.

— David DeSanto

It's about the work, it's not about you.

— David DeSanto (on the value of having 'short toes')

Sometimes it's actually a lot easier to be transparent than it is to not be transparent.

— David DeSanto

You can't be as transparent as we are without having our values, and you can't have our values unless you’re putting them into a remote work environment.

— David DeSanto

It's just software, so anything's possible.

— David DeSanto

GitLab’s culture of radical transparency (public meetings, open handbook, public issue tracker)Core values: kindness, short toes, assuming positive intent, results and efficiencyHow to make all-remote, async-first work at scaleDefining and managing outcomes versus deliverables/hours in product developmentBreadth-over-depth vs depth-over-breadth product strategy at GitLabGitLab’s AI strategy and GitLab Duo across the SDLCHiring, interviewing, and operating as a PM in a remote, highly transparent environment

High quality AI-generated summary created from speaker-labeled transcript.