CEO Shadow Program


This is an overview of the CEO Shadow Program. Please feel free to contact the CEO team, @connor o’brien (Chief of Staff to the CEO) on slack with any questions, comments, feedback, or concerns.

The CEO Shadow Program typically lasts between 1-2 business days. It is a temporary rotation for all eligible teammates where they will get an up-close look at the day-to-day life of the Sourcegraph CEO, Sourcegraph’s business strategies at work, and decision-making at the top. This rotation, if done right, should increase transparency and visibility into how Sourcegraph is run while better enabling the CEO Shadow to work cross-functionally and better align their core work to company strategies after the rotation.

Goal and intention of the program

The overarching goal of the CEO Shadow program is to give eligible teammates broad exposure to every possible facet of the business while working directly with the CEO on a more personal level.

What the CEO shadow program is NOT

The CEO Shadow program is not a professional or leadership development program. Being a CEO Shadow is not related to your performance (though, you must meet the eligibility criteria. Lastly, the CEO shadow program is not “extra work” on top of your job, but different work instead.

Typical responsibilities

As the Shadow CEO, you will have unprecedented access to the CEO / exec team and be exposed to confidential and proprietary information. CEO Shadows must honor the confidentiality of content, topics, and information being discussed.

Additionally, CEO Shadows are expected to do more than just “tag along”. The expectation is the CEO Shadow will meaningfully contribute to conversations, meetings, content development, program / projects, etc. as they are able.

Examples of typical tasks and responsibilities of a CEO Shadow:

  • Provide a “bottoms-up” perspective as you openly, thoughtfully, and respectfully observe, challenge, and collaborate with the CEO and exec team on company business.
  • Help craft weekly priorities for the CEO
  • Take notes (as directed) and follow up on action items, decisions, etc. from the meetings you attend
  • Record an external-facing video / blog post on your experience to help with recruitment, company brand, etc.
  • Train / enable new CEO Shadows for their upcoming rotation.

Past CEO Shadow experiences

Are you curious about other shadows’ experiences? Read about their experiences and takeaways below.

Eligibility & Participation


All Sourcegraph teammates in good standing (i.e. not on a performance plan) are eligible for the CEO Shadow Program.


The CEO Shadow Program typically lasts between 1-2 business days. The length and timing of the rotation is subject to change given Quinn’s and the Shadow’s schedules. The CEO team will do it’s best to keep agreed upon dates, with the understanding there are external factors that cause Quinn’s availability to shift dramatically on a moment’s notice.

Every effort will be made to ensure this program is inclusive. Please reach out to the CEO team, Connor O’Brien (Chief of Staff to the CEO | @connorobrien on Slack) if you have extenuating circumstances that are keeping you from participating in-person and we’ll do our best to accommodate.

Participation in the CEO Shadow Program is not added work to your job. Participating in the CEO Shadow program means you are taking a leave from your core job responsibilites to focus on being a CEO Shadow. Participation in the CEO Shadow program is not PTO as you will be working in a different capacity.

How to apply

  1. Work with your manager and cross-reference this doc to find a few dates that could work.
  2. Once you’ve identified a few dates, please fill out this form to kick off the request process.
  3. You will then be contacted to coordinate and schedule your rotation date(s) and discuss program logistics (where to stay, when to arrive, what to expect, etc.). Most answers to these questions should be answered on this handbook page. If they are not, please don’t hesitate to reach out for clarification.


Travel & Expenses

We encourage upcoming Shadows to review prior shadows blogs / vlogs or reach out to them directly to discuss their experience. You can also reach out to Connor O’Brien (Chief of Staff to the CEO | @connorobrien on Slack).

The CEO Shadow Program is designed to provide a unique and compelling opportunity to all Sourcegraph teammates. Its goal is to be as inclusive as possible, so any and all travel-related expenses (detailed below) will be covered by the program and not draw down from your individual travel budget.

There is a CEO Shadow Spend category that you should tag all rotation-related expenses to.

NOTE: Quinn’s calendar is very fluid. CEO shadows are permitted to book refundable airfare in the event Quinn’s schedule changes resulting in rescheduling your rotation.


Lodging during the CEO shadow program is provided by the company and will only cover for the “active” shadowing period. If traveling a long distance and lodging is needed beyond the rotation, please clear it with @connor o’brien (Chief of Staff to the CEO) first.

Lodging is booked in accordance with our company travel policy. Please book your lodging through Navan.

We recommend staying at the Hotel Kabuki. Hotel Kabuki is in a safe neighborhood with lots of great food options, safe to walk around in, centrally located within SF, reasonably priced but with great amenities, and is easy to get to Quinn’s place or our regularly used WeWorks


Airfare is booked in accordance with our company travel policy. Please book your airfare through Navan.

Transportation to / from the airport

At San Francisco International airport (SFO), all rideshare apps (Uber, Lyft, etc) pick up on level 5 of the parking structure. Taxis pick up on the Arrivals/Baggage Claim Level for all terminals. The BART (Bay Area Rapid Transit / our local metro / train) also runs from SFO to San Francisco.

General transportation

CEO Shadows can expense any and all work-related travel while on your rotation. Please be mindful of what you do / do not expense.

Expensing meals

CEO Shadows should follow our company travel policy in regards to food and dining.


Childcare is covered during the active shadowing period and will be reimbursed via your expense report. We will work with the finance team to enable the correct spend category in Airbase for you to submit expenses against.

CEO shadow rotation exclusions

The CEO Shadow will not participate in board meetings and exec team working sessions / off-sites are dependent on the agenda. Should your proposed rotation need to be moved due to a change in the agenda, we will work with you to find an alternative date for your rotation.

During the rotation, CEO shadows will sit out of 1-1s (unless cleared with the participants beforehand) and will join the ‘closed session’ exec team meeting unle(45 mins).

Blog post / interview

Part of your participation as a CEO Shadow is to create a blog / vlog post about your time as the CEO Shadow.

When is your content due?

All content must be completed by the end of the week of your rotation. We will feature your recap in the GitDown the following Monday.

How is content submitted?

When it is ready, please share your recap via a slack message to Connor O’Brien, Madison Clark, and Amie Rotherham.

What can you write / discuss?

You can write or discuss anything you want (as long as it doesn’t reveal information about anyone or anything that could be considered sensative). All content will be shared, unabridged, with the company and posted in the weekly GitDown.

Some content will be selected for external use (with your approval, of course) by the communications team.

Tips and Tricks to working with Quinn

Working with Quinn is great. As with all people, he has preferences for communication and working styles. In order to make an efficent use of your and Quinn’s time, here are a few guidelines to consider when working with Quinn.

  • Quinn’s in-person style mirrors his writing style closely – brevity, honesty, and directness are preferred.
  • Don’t be afraid to share candid feedback.
  • Quinn really values thoughtful discussions and debates. He will push and challenge you and he expects you to do the same.
  • Meetings are often back-to-back with short 5-15 minute breaks built in. Be mindful of this time before starting a converation on a topic that may require more than the time available.