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Sid Sijbrandij: How I Founded GitLab; Remote Work vs In-Person; CEO Coaches | 20VC

Sid Sijbrandij is the Co-founder & CEO @ GitLab. GitLab’s single application helps organizations deliver software faster and more efficiently while strengthening their security and compliance. Prior to their IPO last year, Sid raised funding from some of the best including ICONIQ, GV, Tiger, Coatue and D1 to name a few. Under his leadership, the company has grown to over 1,500 employees and over 30 million registered users. If that was not enough, Sid is also an active angel and sits on the board of Meltano, a spinout of Gitlab that allows you to manage all the data tools in your stack. ------------------------------------------------ In Today’s Episode with Sid Sijbrandij You Will Learn: 1.) The Founding of Gitlab: -How did Sid make his way into the world of tech and startups? -What was it about Gitlab as a project that excited Sid so much from Day 1? -How did Sid convince his co-founder to turn Gitlab from a project into a company? 2.) The Future of Work: -Why does Sid believe it is a fallacy that everyone will go back to the office? -What are the 1-2 most important things for companies to do when moving to a remote work environment? Where does Sid see many make mistakes? -What have Gitlab done to create a remote working environment so successfully? What have they tried that has not worked? -What stage of company building does remote work best for? When is it most challenging? 3.) Sid: The Leader -How has Sid changed and evolved as a leader over the Gitlab journey? -How does Sid look to get as much feedback as possible on his leadership? -How does Sid create an environment of safety where everyone feels they can provide feedback? -How does Sid work with his CEO coach? Should every CEO have one? -What should one look for in them? How do you know when you need to change your CEO coach? 4.) Sid: The Board Member -What have been Sid’s biggest lessons on what makes successful board management? -In prep for the meeting, what materials does Sid provide? When does he send them? Does he present to the board? What mistakes do founders make in boards? -From being on the other side as a board member, what does Sid believe the best members do? -What would Sid most like to change about board meetings today? ------------------------------------------ #GitLab #SidSijbrandij #20VC #VentureCapital #HarryStebbings

Sid SijbrandijguestHarry Stebbingshost
Mar 20, 202241mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

GitLab CEO Sid Sijbrandij on Remote Work, Leadership, and DevOps Platforms

  1. Sid Sijbrandij, co-founder and CEO of GitLab, recounts how GitLab grew from an open source project into a 1,500+ person, fully remote public company and DevOps platform leader.
  2. He explains why remote-first was both organic and intentional, emphasizing structured informal communication, written culture, and asynchronous work as core enablers of scale.
  3. Sid dives into his leadership evolution—delegation, transparency with guardrails, feedback culture, and situational leadership—plus the critical role of CEO coaches and well-run boards.
  4. He also outlines why DIY DevOps toolchains are “dead,” the rise of unified DevOps platforms, and how his new vehicle, Open Core Ventures, is creating companies around open source projects.

IDEAS WORTH REMEMBERING

5 ideas

Remote work scales better than co-located work, but requires deliberate support for informal communication.

GitLab found remote becomes more advantageous as headcount grows, yet companies must intentionally create ‘water cooler’ moments—like coffee chats and optional team hangouts—to build trust and culture.

Hybrid only works when everyone’s in the office on the same days; mixed remote/in-office hierarchies fail.

Sid argues the successful hybrid model synchronizes office days, while setups where some are always remote and others mostly in-office push top remote talent to leave for fully remote environments where they’re on equal footing.

Strong written and asynchronous cultures reduce dependency on meetings and increase clarity.

GitLab’s 2,000+ page handbook and norm of ‘no presenting in meetings’ free meetings for Q&A and decisions, but Sid notes that for urgent, high-stakes, low-context topics, synchronous conversations are still best.

Transparency should be ‘by default’ but with clearly defined, explicit exceptions.

GitLab publishes a long list of non-transparent topics (e.g., salaries, M&A) while sharing broadly elsewhere; this clarity prevents confusion and allows openness without undermining sensitive processes.

Cultivating psychological safety around feedback requires public gratitude, never punishing messengers, and self-critique.

Sid emphasizes openly thanking people for feedback (even when wrong), banning blame-the-messenger remarks, and modeling self-criticism so others feel safe challenging even the CEO’s behavior.

WORDS WORTH SAVING

5 quotes

Remote works better the bigger you are… if you're 1,500 people, you can't be in the same room anymore.

— Sid Sijbrandij

When people say they long back to the office, they don't mean the furniture.

— Sid Sijbrandij

At GitLab, you're not allowed to present in meetings… in the call, it's just Q&A.

— Sid Sijbrandij

Feedback doesn't have to be correct in order for you to welcome it.

— Sid Sijbrandij

DIY DevOps is dead… selecting 10 best-in-class solutions and maintaining custom integrations is no longer working.

— Sid Sijbrandij

Origin and evolution of GitLab as a DevOps platform and companyRemote-first work: philosophy, practices, and the future of work modelsAsynchronous communication, written culture, and informal connection at scaleLeadership style, feedback culture, and situational leadershipTransparency boundaries, iteration, and decision-makingCEO coaches, mentorship, and managing vs. serving on boardsDevOps market shift from DIY toolchains to integrated platforms; Open Core Ventures

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