Jul 19, 2019 · 25m · 20vc
20VC: Gitlab Founder, Sid Sijbrandji on Lessons From Scaling from 400 to 1,000 People in 1 Year, Why You Have To Have A Low Level Of Shame On The Product You Release & The Secret To Making Remote Work So Effectively At Scale
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The 20 VC, host Harry Stebbings interviews GitLab founder and CEO Sid Sijbrandij to discuss building a single-application DevOps platform, scaling an all-remote workforce, and leveraging radical transparency and low-shame feature releases to drive community growth.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 42.6% of the talking time here. How this is scored →
Harry as informed peer 2.3 Guest teaching 4.3 Guest disagreement 1.1 Harry pushing back 1.6
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 20:09 Rejecting common motivational advice
Sid candidly rejects the popular cliché 'you can do anything you want', reframing it around practical skill, interest, and market demand.
Hardest push from Harry ▶ 14:32 Challenging lack of product focusHarry directly questions Sid's broad product strategy, asking if he disagrees with conventional wisdom around simplicity and startup focus.
Biggest teaching moment ▶ 12:45 Lesson on integrated vs separated DevOps toolsSid admits how industry conventions and even his own initial assumptions were wrong regarding separate CI tools, demonstrating how integrated single-application DevOps provided superior user value.
Harry holds his own ▶ 11:22 Leveraging investor intelligence on product strategyHarry draws on insights from GitLab's board investors to drill into the tactical decision between product depth versus breadth.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| The Founding Story and Early Days of GitLab | 1 | 3 | 0 | 0 | Harry asks standard origin story questions to introduce GitLab's beginnings. Sid explains how he started gitlab.com and wired money to the original open-source creator in Ukraine via Western Union. | |
| Cultivating Trust and Scaling an All-Remote Organization | 2 | 4 | 0 | 1 | Harry asks about Sid's personal trusting nature and how all-remote operations scale across time zones. Sid educates Harry on how smaller iterations lower coordination costs and how a 3,000-page handbook eliminates shoulder tapping. | |
| Maintaining Accountability and Mitigating Risk Through Iteration | 3 | 5 | 2 | 3 | Harry challenges Sid on whether publishing product roadmaps gives competitors a net-negative advantage. Sid reframes this by explaining that competitors waste time watching roadmaps while GitLab gains crucial early customer feedback. | |
| Product Strategy: Breadth vs. Depth and Concurrent DevOps | 4 | 6 | 3 | 3 | Harry uses investor feedback to challenge Sid on prioritizing product breadth over depth, questioning the departure from startup focus. Sid explains how he was initially wrong about combining CI and version control, concluding with the insight that tech businesses are either bundling or unbundling. | |
| Low Level of Shame and Community-Driven Refinement | 2 | 4 | 0 | 1 | Harry asks about maintaining a low level of shame when releasing product features. Sid outlines how shipping early, incomplete iterations relies on community contributions to refine features over time. | |
| Public Strategy as a Competitive Advantage | 2 | 4 | 1 | 1 | Harry inquires about public strategy and remote team management lessons. Sid argues that internal misalignment hurts companies far more than competitors knowing their strategy, so public strategy acts as an opt-in filter for hires. | |
| Quickfire Round: Management, Hiring, Monetization, and Vision | 2 | 4 | 2 | 2 | In the quickfire round, Harry asks rapid questions on books, compensation, and advice. Sid contrarianly rejects the cliché 'you can do anything you want' in favor of matching personal strengths with market demand. |
Statements from this episode (23)
GitLab Scaled Remote Team to Over 762 People Across 55 Countries
“Sid has scaled the team to over 762 team members across 55 countries, a fully remote team”
Sijbrandij: GitLab open-source project reached 300 contributors in year one
“I checked out the project and it already had 300 people contributing to it in the first year.”
Sijbrandij: Majority of GitLab revenue comes from self-hosted deployments
“The majority of our revenue is still coming from self-hosted.”
Sijbrandij: GitLab will grow from 400 to 1,000 employees this year
“GitLab is now 650 people. We're growing this year from 402,000 people.”
Sijbrandij: Smaller project scope reduces cross-department coordination costs
“And the smaller the thing you do, the less coordination it requires. If you're doing a six month thing, you better make sure that all the departments across the company are bought into that. If you're doing a two day thing, you can just do it, release it.”
Sijbrandij: GitLab's public employee handbook is over 3,000 pages long
“We have a handbook. It's public and creative comments. So lots of people are copying from it and being inspired by it, but it's over 3000 pages and it contains many of the things you would normally not find documented at other companies.”
GitLab measures employee performance by output rather than hours worked
“There is accountability for results at GitLab. Very much so. Like, results is our number one value, and we said, like, we measure your results, not your hours, so you're absolutely on the hook for producing.”
GitLab maintains monthly releases and rarely has project delays over six months
“So we have very few kind of canceled projects, and if something runs late, the worst thing at GitHub is if you miss a release. We have a monthly release, and then instead of one month, it takes two months, and that tends to happen, but we don't have things tha…”
Sijbrandij: Competitors try to front-run GitLab releases using its public roadmap
“Sometimes our competitors know that we're going to release something and they try to kind of front run us by day or so.”
Sijbrandij: Public Roadmaps Net Positive Because Building Customer Needs Trumps Secrecy
“But all in all, it's been a very positive thing for us because the most important thing about your roadmap is not that it's a secret, but that it's correct that you're making the stuff that customers want.”
Sijbrandij: GitLab has evolved to have ten times the scope of GitHub
“GitLab started off as a being inspired by GitHub, and it's now evolved into a product that has a scope that is 10 times the scope that GitHub has.”
Sijbrandij: Ban the word 'obviously' to encourage open debate and clarification
“We should never use the word obviously. Because it discourages people from challenging what you just said or asking for clarification.”
Sijbrandij: Releasing incomplete software with low shame enables community product flywheels
“In a very small iteration, so sometimes the stuff we release, we have a low level of shame about them. They're not complete, and we know it, but it allows people from the community to come in and contribute to it, and by contributing to it, they make it accept…”
GitLab receives over 190 monthly improvements from its open-source community
“Every month we have over a 190 improvements that come from the wider community.”
Sijbrandij: GitLab's co-founder lacked running water when he launched the project
“When he started GitLab, he didn't have running water in his house, and he didn't have great collaboration software, and he picked the thing that wouldn't cost any money to make, because he was a developer, he could make this himself.”
Sijbrandij: Searching 'GitLab CEO pricing' reveals all company monetization logic
“If you type GitLab CEO pricing, you'll find exactly all the considerations we make pricing and why we charge for certain features and not others.”
Sijbrandij: Operational transparency is a highly effective recruiting tool for aligned talent
“So transparency started as a value because it was really, really important to keep in touch with the community. Later on, we realized it's also a great way to recruit people who are aligned with what you do.”
Sijbrandij: Companies suffer more from internal strategy secrecy than competitor awareness
“Yeah, I think a lot of companies are kind of hesitant to articulate and disseminate their strategy to make it public or to even share it within the company. And there's benefits from your competitors not knowing your strategy, but I've seen a lot more companie…”
Sijbrandij: Operating an all-remote company is easier than managing a hybrid workplace
“I think being all remote is a lot easier than being hybrid. Where part of your people are co-located and part are not.”
GitLab hosts company-wide gatherings every nine months alongside daily non-work breakout calls
“So at GitLab, we have a lot of different mechanisms in which we allow people to learn together, know each other outside of it like a transactional work setting. Examples are the coffee chats, travel stipends. We have a nine-monthly get-together, but also every…”
Sijbrandij: GitLab pays remote employees location-based rates, not uniform global salaries
“We pay people differently. We have a blog post about it, why we pay people local rates.”
Sid Sijbrandij: Open-source projects should monetize when paying buyers request features
“So if the people asking for features are people that can pay for them, it's probably good to start monetizing.”
Sid Sijbrandij: Software shipping should fix deadlines and reduce feature scope
“We always say that time is fixed, and then the scope is variable, so great, if you have a hard time meeting the deadline, just cut down the scope, do less, and I think that's been very great, so just stick to your deadlines.”