Jul 11, 2019 - Tye Davis    

Without a shadow of a doubt: Inside GitLab's CEO shadow program

Technical marketing manager Tye Davis did everything from joining investor meetings to battling with the flight simulator at GitLab Mission Control.

Walking up to the iconic Millennium tower on Monday, I was a bit nervous for my first day of the GitLab CEO shadow program. Sometimes, our impression of the CEO is someone who is intimidating and strictly business; they only care about things work related. That persona often results from not having access to the CEO, and the fear that one mistake in their presence may cost your job. The GitLab CEO shadow program proved to be a pleasant departure from this mindset.

Entering GitLab “Mission Control,” I was met with a large apartment turned into a hybrid boardroom with a touch of living space. This is a unique working environment because GitLab is an all-remote company that allows GitLab team members to work from their choice of location (home, coffee shop, van, shared workspaces, surfboard, etc.). So, although you are physically at "Mission Control," most of the CEO shadow program is done via video conferencing. There is no need to go from physical meeting room to meeting room, you simply go from conference call to conference call (woo efficiency!). Six monitors add to the office-like feel of the living room, displaying (amazing) sales data, locations of team members in over 50+ countries, and the DevOps toolchain landscape that GitLab replaces. The boardroom also offers access to gaming systems, a flight simulator and readily available drinks and snacks. I was able to calm my excitement and I settle into the room with the fellow CEO shadow, Mayank.

Mission Control center Inside GitLab's "Mission Control."

Hitting the ground running

My first face-to-face meeting with CEO Sid Sijbrandij was on our first CEO-specific call of the day, a public live stream on "Sid's three biggest remote work challenges" with Leo Widrich, co-founder of Buffer. This was the first ice breaker into the CEO shadow program and helped me understand just how inclusive the shadow program is. Sid really made us feel like we belonged on the call by incorporating us into the discussion. His inclusivity lowered my stress a few notches, and I began to understand what was to come in the next few weeks: transparency.

The second meeting took the inclusivity of the program a step further, as we joined a group call with the executive team from across the GitLab organization (aka the E-group). You might expect some hesitation in allowing someone who is not an executive to join a meeting where top-level matters are discussed, but the CEO shadow program was made exactly for these types of experiences. The program gives participants full visibility into every working part of building an enterprise company. There was no resistance from the E-group team and upon joining the meeting, I was met with an overwhelming ‘welcome’ to our working session. This alleviated most of my nervousness and truly showcased GitLab’s collaboration value by displaying ‘no ego’ and ‘kindness’ from the executive team.

The feeling of welcomeness was constant

There were very few circumstances where Mayank and I were not included in meetings due to the sensitivity of the subject. The most eye-opening experience for me was meeting with potential investors in GitLab that represent some of the largest and best-known investment firms in the world. These organizations discussed topics around GitLab’s vision and technology and the firms said they see the incredible upside of GitLab. If I was only able to attend one meeting during the whole program, I would choose this one. My confidence in the direction this company is taking has increased after seeing firsthand how much interest there is from investors in GitLab’s growth. Observing the amount of planning leading up to these meetings between Sid and Paul, our CFO was a great learning experience. Investors are excited about the future of GitLab as a result of all of the hard work of every GitLab team member. My only disappointment is that the program is only two weeks long and that I won’t get to continue to be part of these developing relationships.

Shadowing the CEO Doing my best impression of shadowing the CEO's activity in his everyday engagements

Takeaways

The shadow program was an incredibly enlightening experience. Joining this program gave me an accurate and deeply intuitive understanding of the life of a CEO. Sid has mastered the high velocity of responsibility and full situational awareness that is needed to effectively lead our company as CEO. He also acknowledges that he always has room for improvement – so much so that he has a section of flaws that are listed on the GitLab CEO handbook page. One big takeaway from the shadow program is listed on the CEO page. This is something I believe is the biggest factor to collaborate effectively is what Sid notes about his approach, “Not a flaw but something to know about me, I have strong opinions weakly held. Or, as someone said, I come in hot but am open to new evidence.” This is applicable across the company (and personally) as we all iteratively build a tool that best fits our customer needs, and we must be receptive of adjusting accordingly if new evidence corrects our product vision.

Business aside, Sid has some pretty funny GitLab stories. If you ever get the chance to ask him about Burning Man, I promise it’ll be a good laugh. My time in the CEO shadow program was unique, educational, and inspirational. I am thankful for this opportunity and hope that one day I’ll reciprocate in a future exec role. Extra shout out to Cheri who coordinates diligently so that all of us CEO shadows are set up for success. Looking back, the most stressful part of the CEO shadow program was the anxiety the X-Plane flight simulator brought when trying to land an airplane (the landing didn't go well).

Photo by Landry Gapangwa on Unsplash

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