CEO Shadow Program


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

The CEO Shadow Program typically lasts between 1 and 5 business days (1 business week). 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 core work. CEO Shadow rotations should be treated as paid leave by their department and the teammate.

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 how other shadow’s experiences? Hear from them yourself about their experiences and takeaways.

Eligibility & Participation


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


The CEO Shadow Program typically lasts between 1 and 5 business days (1 business week). The length and timing of your shadow program is subject to change given Quinn’s and the Shadow’s schedules. The CEO team will do it’s best to not deviate from the pre-agreed dates, but please understand there are external factors that cause Quinn’s availability to shift dramatically on a moment’s notice.

This program is intended to be in-person and is a break from our async culture. However, given the goal and intention of the program, the CEO Shadow program should be an exception. Every effort will be made to ensure this program is as inclusive as possible. Please reach out to the Chief of Staff to the CEO (@connor o’brien on slack) if you have extenuating circumstances that are keeping you from participating and we’ll do our best to accommodate.

Participation in the CEO Shadow Program is not additive work to your day 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 will not draw down from your available PTO as you will still be working, but 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. The Executive Business Partner to the CEO (@sally voisen on slack) will then reach out to coordinate and schedule your rotation date(s).
  4. After your rotation date(s) have been scheduled please reach out to the Chief of Staff to the CEO(@connor o’brien on slack) to discuss program logistis (where to stay, what to do, 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.


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 the Chief of Staff to the CEO directly (they will alos proactively reach out to you if there is anything specific Quinn would like to work with you on).

Travel & Expenses

The CEO Shadow Program is designed to provide a unique and compelling opportunity to any and all Sourcegraph teammates. It’s aim 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.


Lodging during the CEO shadow program is provided by the company and will only cover for the “active” shadowing period. If travling a long distance and loding is needed over the weekend, please clear with the Chief of Staff (@Connor O’Brien )first.

Lodging is booked in accordance with our company travel policy. We use TripActions.


Airfare is booked in accordance with our company travel policy. We use TripActions.

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.

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.

Required Business Travel

The CEO shadow will accompany the CEO on any and all business travel.

Off-sites and Board Meetings

The CEO Shadow will not participate in Exec Team Off-site or Board meetings. Should a rotation fall over one of those events, the CEO Shadow rotation will split the weeks to fall before and after the off-sites / board meetings.

Blog post / interview

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

When is your content due?

Your content must be completed within 1 week of the completion of your rotation.

How is content submitted?

All content must be completed within 1 week of your CEO Shadow rotation. When it is ready, upload to the CEO Shadow Content google drive and @ mention Amie Rotherham, Director of Global Communications.

What can you write / discuss?

You can write or talk about anyone or anything you want. All content will be shared, unabridged, with the company and stored in the CEO Shadow Content drive folder after submission and posted to the CEO Shadow Handbook page.

Some content will be selected for external use (with your approval, of course) by the communications team. If they believe your content should be in our Handbook, Blog, or another external medium, they will reach out to you to collaborate. We hope you choose to share your great content with the world!

Tips and Tricks to working with Quinn

Working with Quinn is great. As with all people, we have our preferences for communication and working styles. In order to make your and Quinn’s time the most efficient, here are a few guidelines to consider when working directly with Quinn.

Speaking and Communication

  • Quinn’s in-person style mirrors his writing style closely. When engaging with Quinn, 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.