Gitlab hero border pattern left svg Gitlab hero border pattern right svg

CEO Shadow Program

On this page


The CEO shadow program at GitLab is not a job title but a temporary assignment to shadow the CEO. The shadow(s) will be present at all meetings of the CEO. GitLab is all remote but sometimes the CEO has in-person meetings. Therefore, you will live in San Francisco during the entire rotation and travel with the CEO.


The goal of the shadow program is to give current and future directors and senior leaders at GitLab a overview of all aspects of the company. This should lead to leadership who are able to do global optimizations.


You will attend all meetings of the CEO, this includes but not limited to:

  1. 1-1s with reports
  2. interviews with applicants
  3. conversations with board members

You will travel with the CEO to meetings, team off-sites and conferences outside of San Francisco per the CEO's schedule. EA to the CEO will assist you with conference registration and travel accommodations during these time frames.

The CEO's executive assistant should ask external people if they are comfortable with the shadow joining prior to the scheduled meeting and will share a link to the CEO Shadow page to provide context.

These meetings can have different formats:

  1. video calls
  2. in-person meetings
  3. dinners that are business related
  4. customer visits
  5. conferences

You will not attend when:

  1. Someone wants to discuss a complaint and wants to stay anonymous.
  2. If any participant in the meeting is uncomfortable.
  3. If the CEO wants more privacy.

This is probably the most open program in the world. It depends on the participants respecting confidentiality, during the program, after the program, and after they leave GitLab.

Rotation rhythm

We want many people to be able to benefit from this program, therefore we rotate often. It is also important that an incoming person is trained so that the management overhead can be light. Therefore we decided to make a rotation two weeks:

  1. See one, you are trained by the outgoing person.
  2. Teach one, you train the incoming person.

The shadow should be available for the full two weeks. When the CEO has a week or more of paid time off or during Contribute the shadow program will pause, one shadow will see one before and teach one after that time.

We want this program to be as accessible as possible to team members. These rotations spanning one or more weeks without a shadow are great if you can't to be away from home for more than one week at a time. Also, if you'll need childcare to be able to participate, GitLab will reimburse you for it.

For new team members this might be the first thing they do after completing our onboarding.

Planned rotation

Start date End date See one Teach one
2019-04-15 2019-04-19 Mayank Tahil - Alliances Manager None
2019-04-22 2019-04-26 Mayank Tahil - Alliances Manager None
2019-04-29 2019-05-03 Tye Davis - Technical Marketing Mayank Tahil - Alliances Manager, Alliances
2019-05-06 2019-05-10 No Shadow - Contribute No Shadow - Contribute
2019-05-13 2019-05-17 No Shadow - Contribute No Shadow - Contribute
2019-05-20 2019-05-24 No Shadow - CEO Summit No Shadow - CEO Summit
2019-05-27 2019-05-31 John Coghlan- Evangelist Program Manager, Marketing Tye Davis - Technical Marketing
2019-06-03 2019-06-07 Cindy Blake - Sr Product Marketing Manager, Security Specialist, Marketing John Coghlan- Evangelist Program Manager, Marketing
2019-06-10 2019-06-14 Nnamdi Iregbulem - MBA Candidate at Stanford University Cindy Blake - Sr Product Marketing Manager, Security Specialist, Marketing
2019-06-17 2019-06-21 Clinton Sprauve - Technical Marketing Manager Nnamdi Iregbulem - MBA Candidate at Stanford University
2019-06-24 2019-06-28 Lyle Kozloff - Support Engineer Manager Clinton Sprauve - Technical Marketing Manager
2019-07-01 2019-07-05 No Shadow - Vacation No Shadow - Vacation
2019-07-08 2019-07-12 Marin Jankovski - Engineering Manager, Delivery Lyle Kozloff - Support Engineering Manager
2019-07-15 2019-07-29 No Shadow - Vacation No Shadow - Vacation
2019-08-05 2019-08-09 Emilie Schario - Data Analyst, Finance Marin Jankovski - Engineering Manager, Delivery
2019-08-12 2019-08-16 Kenny Johnston - Director of Product, Ops Emilie Schario - Data Analyst, Finance
2019-08-19 2019-08-23 JJ Cordz - Marketing Operations Manager Kenny Johnston - Director of Product, Ops
2019-08-26 2019-09-06 No Shadow - Vacation No Shadow - Vacation
2019-09-09 2019-09-13 Clement Ho - Frontend Engineering Manager, Monitor JJ Cordz - Marketing Operations Manager
2019-09-16 2019-09-20 Eric Brinkman - Director of Product Clement Ho - Frontend Engineering Manager, Monitor
2019-09-23 2019-09-27 Danielle Morrill - General Manager, Meltano Eric Brinkman - Director of Product
2019-09-30 2019-10-04 No Shadow - Vacation No Shadow - Vacation
2019-10-07 2019-10-11 No Shadow - Vacation Danielle Morrill - General Manager, Meltano

What to expect

  1. This isn't a performance evaluation, so get comfortable.
  2. You do not need to dress formally, so business casual clothes are appropriate. For example, Sid wears a button up with jeans.
  3. Review Sid's calendar to get an idea of what your upcoming weeks will be like.
  4. Review and update the ongoing CEO agenda. This agenda contains TODOs, documentation items, training, and feedback information items.
  5. Be ready to observe and ask questions.
  6. Give and receive feedback from Sid.
  7. Don't plan to do any of your usual work. Prepare your team as if you were on vacation.
  8. Expect to add a number of handbook updates during your shadow period.


Since a rotation is over a short period there are no long running tasks that you can assume.

The tasks consist of short term tasks, for example:

  1. Make handbook updates
  2. Iterate and complete small tasks as they come. Clear them out immediately to allow for rapid iteration on more crucial tasks.
  3. Draft email responses
  4. Solve urgent issues, for example a complaint from a customer or coordinating the response to a technical issue.
  5. Prepare meetings.
  6. Take notes during meetings.
  7. Follow up on meetings (improve the notes, followup appointment, thank you cards, swag).
  8. Ensure that internal teams are updated with action items and outcomes
  9. Compile a report on a subject.
  10. Write a blog post based on a conversation.
  11. Editing a recorded video.
  12. Promoting the work you created.
  13. Writing a blog post about something you learned or your experience.
  14. Camerawork for a video.
  15. Control slides and muting during the board meeting.
  16. Set up for an in-person meeting.
  17. Receive guests.
  18. Add to the documentation of GitLab.
  19. Do and publish a CEO interview.
  20. Add training for this program to the handbook.
  21. Training the incoming shadow program person.
  22. Speak up when the CEO displays flawed behavior.


For now this role is called a CEO shadow to make it clear to external people why a shadow is in a meeting.

Other names considered are:

  1. Technical assistant. Seems confusing with executive assistant. "In 2003, Mr. Bezos picked Mr. Jassy to be his technical assistant, a role that entailed shadowing the Amazon CEO in all of his weekly meetings and acting as a kind of chief of staff. "
  2. Chief of Staff. This commonly is the "coordinator of the supporting staff" which is not the case for this role since people rotate out of it frequently. The executive assistants reports to peopleops.
  3. Global Leadership Shadow Program is too long if only the CEO is shadowed.

CEO Shadow Introductions

First state that you're a CEO shadow for two weeks, then that your normal role is X.

Documentation focus

A ongoing shadow program with a fast rotation is much more time consuming for the CEO then a temporary program or a rotation of a year or longer. Therefore most organizations either have a shadow for two days or have someone for a year or more. We want to give many people the opportunity to be a shadow so we rotate quickly. To make this happen without having to invest a lot of time to train people coming in we need great documentation. Therefore a quick turnaround on documentation is of paramount importance. And the documentation will have a level of detail that isn't needed in other parts of the organization.


You are eligible to apply for the program if you havev accepted an offer at GitLab as a:

  1. Manager or up
  2. Staff backend engineer or up since we have a dual career track for engineering.
  3. Individual Contributor and you belong to an underrepresented group as defined in our referral bonus program.
  4. There is a last minute cancellation and we open the program up to all Individual Contributors at GitLab.


Expenses, travel and lodging

Lodging during the CEO shadow program is provided by the company. CEO executive assistant books the accomodation based on availability and cost. You can express your preference (hotel or AirBnB) via email to the EA in question, however the final decision is made by the EA based on the distance from CEO and costs. EA will provide the accomodation details no earlier than 1 month and no later than 2 weeks before the scheduled rotation.

Accommodation is provided only for the active shadowing period, it is not provided during the shadow program pause (cases when the CEO is unavailable). In case you are coming from a timezone that is more than 6 hours difference with Pacific Time, it is possible to book the weekend before the first shadow work day to adjust to the new timezone.

Airfare can be booked according to our travel policy or spending company money policy. In case your shadow rotation includes time without shadowing, it is possible to expense airfare to fly home and back within the continental USA. If you are from outside of the USA, it is also possible to expense airfaire during the time without shadow because of the possible high cost of lodging in San Francisco if you chose to stay at a different location.

Training checklist

Outgoing shadows are responsible for training incoming shadows. Here's a list of things to make sure you cover:

  1. Boardroom location & WiFi.
  2. Set a meeting time and place for the incoming Shadow's first day. The Outgoing Shadow will give the Incoming Shadow access to the boardroom.
  3. At the start of the week, review your calendar and Sid's. If a meeting wasn't added to your calendar and looks like it should be, reach out to CEO executive assistant to confirm if you should be invited or not. There will be some meetings and events the Shadow does not attend.
  4. Discuss coordinating schedules and key access to avoid ringing Sid.
  5. How to set up the board room for in-person meetings (boardroom TV, answering the phone, greeting the guest).
  6. How to update the boardroom TV screens.
  7. When to show up to the boardroom, getting to events, dinners, etc.
  8. How to set up a livestream. Make sure you are added as a co-host for any planned livestreams ahead of time.
  9. Ensure incoming Shadow has access to the CEO Shadow agenda and knows how to make changes to the handbook.

When to show up to the boardroom

You are welcome to work from the boardroom but its not required to be present in-person unless there is an in-person meeting, event, or dinner. It's up to you to manage your schedule and get to places on time. If you are traveling somewhere, meet Sid at the boardroom at the beginning of the alloted travel time listed on the calendar.

If there is a day during your program where all meetings are Zoom meetings, you can work from wherever you want, as your normally would. You can work from the boardroom if you prefer. If you decide to split your day between remote work and working from the boardroom, make sure you give yourself enough time to get to the boardroom and set up for the guest. It's OK to join calls while mobile.

Boardroom access

When entering the building, the doorperson will ask who you are there to see. Don't say "GitLab" since there is no GitLab office. The doorperson will direct you to the correct lobby.

There is one set of keys so the shadows will need to coordinate access to the boardroom. The fob is for the elevator and the key is for the boardroom.

Boardroom TV

We have monitors in the boardroom. One of them has our sales dashboard, you can configure this with:

  1. Go to Clari
  2. Go To Pulse tab
  3. Open the left side bar
  4. Click on the funnel icon. Select “CRO”
  5. Click on the gear icon. Go to Forecasting. Select Net IACV.

Use one monitor for 'this quarter' and one for 'next quarter' (blue link near the top).

Boardroom Guide

  1. Everything in the fridge that is liquid can be drank including Soylent and alcohol
  2. Thermometer located next to Kitchen entrance
  3. Lighting located next to Kitchen entrance

Switching the mouse and keyboard control

The wireless mouse and keyboard are connected to the middle, bottom TV by default. To update the view on another TV, you have to connect the wireless keyboard and mouse to the desired screen.

  1. Find the USB jacks and Logitech receiver underneath the bottom, right TV.
  2. Connect the Logitech receiver to USB receiver for the desired screen.

Office Preparation Guide

In preperation for guests (customers, investors, etc.) who will be meeting with Sid at the Boardroom, please note the following prior to the meeting start:

  1. All Gitlabbers sit on one side. This allows for easy communication to the guests
  2. Have drinks available on table (from the fridge)

What is it like?

  1. Day 2 of Erica Lindberg
  2. Acquisitions, growth curves, and IPO strategies: A day at Khosla Ventures

CEO shadow program alumni

Start date End date Name Title
2019-03-18 2019-04-05 Erica Lindberg Manager, Content Marketing
2019-04-01 2019-04-19 Michael Fahey Security Manager, Red Team