GitLab: Damnable Iteration and Art Indeed

By Matt Jacobson | October 14, 2021

As GitLab – a single application for the entire DevOps cycle – embarks on its newest chapter as a public company, we find ourselves revisiting early meetings with Sid Sijbrandij, co-founder and CEO at GitLab, and the values engrained from this incredible team. My former colleague and friend Nnamdi Iregbulem had been following the business for several years, and we finally scheduled a meeting with Sid. We arrived at the location on a nondescript street in SoMa. When we knocked on the door, Sid let us into his living room. We had experience partnering with many other remote-first companies like Articulate, Automattic, and InVision prior to this encounter, but had never before done a first meeting in a living room!

We started the meeting sitting in front of Sid’s towering wall of monitors showing every near real-time KPI of GitLab and began the conversation. We were struck by the fact that, for even the questions we asked that we thought might be sensitive (such as the product roadmap), Sid graciously accessed a publicly available GitLab page that had all of the information we could have asked for available to the world. We thought A.) we should have been better prepared for this meeting and B.) this is a founder who is deeply committed to transparency!

A few months later, we heard from Sid that he was thinking about a Series D. We literally dropped everything and returned to his living room (albeit a different one) to discuss. We came away from the update convinced of Sid’s vision and conveyed our unbridled enthusiasm. The next day, I got a message from Sid inviting me to dinner that evening. Joined by Sid’s partner, Karen, we had an amazing discussion, and I learned about Karen and Sid’s self-taught experiences in coding and Ruby-on-Rails, their journey from their native Netherlands, and their eclectic professional experiences including bug bounties and engineering recreational submarines. As dessert came, Karen excused herself for a moment and by the time she had returned, we had outlined and agreed to an investment and business partnership. In typical transparent GitLab fashion, Sid immediately posted a photo of us shaking hands to a public GitLab Slack channel.

In the many years since we led the Series D and subsequently the Series E, we have seen GitLab rise to become the market leading DevOps Platform that enables its customers to transform into software-led businesses. Most importantly, GitLab is a deeply values oriented company, and we have learned a tremendous amount from them in how to build an enduring organization and culture:

We have learned about how world-class teams collaborate. The company has built a first-rate management team that includes Eric Johnson (CTO) and Scott Williamson (Chief Product Officer) delivering category defining products that users love, Michael McBride (CRO) and Craig Mestel (interim CMO) serving our global, diversified customer base and Brian Robins (CFO), Robin Schulman (CLO), and Wendy Barnes (Chief People Officer) supporting our business and over 1,350 team members with strength and success. The team underpins everything with kindness and engages without ego. In an all-remote framework, we have seen them come together consistently on major projects that span the full organization. They live and breathe the idea that everyone can contribute. As a result, the cross functional engagement is some of the best we have experienced.

We have learned what it means to truly seek results. From our first meeting, GitLab has been insanely ambitious along their path to building The DevOps Platform. Ambition is an amazing starting point, but GitLab’s focus on results has also been palpable. A sense of urgency rushes through the company’s veins and has propelled them to some of the fastest product velocity we have ever seen. The team focuses on documentation and measurability with public OKRs. They are disappointed when they do not achieve every goal but set the bar high and dust themselves tenaciously off to propel short term failure into long term endurance.  As an example of this, after we led the Series E, the company saw some growing pains as all great companies do, but they took ownership, reset expectations, and persevered through it as a team.

We have learned about efficiency. The GitLab team writes things down and is respectful of time. Every meeting has a linked agenda and documented outcome. They are not afraid to end an hour-long scheduled meeting after 10 minutes if the meeting’s goals have been achieved. We have embraced many of these principles about efficiency as ICONIQ grows over time, including in the way we run and manage our own meetings and 1:1’s.

GitLab has been intentional in building a diverse, inclusive, and belonging work experience. They bias to asynchronous communication and lean into uncomfortable conversations. They recognize the overlap between work and life and support family and flexibility. They embrace quirkiness and use thoughtful language. I once recall touring a house with Sid where I innocently referred to a bedroom as the “master bedroom.” In his very accepting and open way, he corrected me and said it was the “main bedroom,” explaining the etymology behind some of the words we use.

GitLab embraces iteration in ways we have never seen before. Whether it is a software release or an internal team project, GitLab breaks work into the smallest unit possible, gets it out there, and works with users and customers to learn how to improve. When we asked Sid once about the company’s successful product velocity, he said, “we have a low level of shame.” Many software companies as successful as GitLab in their first product would create a higher bar for additional products. GitLab is not that precious, they start at the minimum viable level and work with customers and users to improve rapidly over time.

GitLab thrives in a culture of transparency. The GitLab handbook is one example of documented culture. They publish their handbook, roadmap, and detailed aspects of their product and operational cadence to the world in a default public view. They believe this transparency builds trust and accountability and allows the organization to scale. From our first meeting with Sid to our countless 1:1’s over the years (with CEO shadows), GitLab stands alone in its commitment to transparency.

Starting from our first investment to internalizing the GitLab Way via the prism of its values, we continue to learn avidly through the GitLab experience. What is even more powerful is the effusive feedback we constantly receive from founders of all stages, globally, thanking GitLab for their formative influence in helping build their own companies, especially in the last 18 months with companies being forced to embrace remote work more meaningfully.

GitLab has blazed a unique and exciting path in this world. We are proud of our partnership and we are enthusiastic about the meaningful journey ahead with so much yet to be done!