The Chief of Staff role in Silicon Valley

URL: https://medium.com/chiefofstaffnetwork/the-chief-of-staff-role-in-silicon-valley-182eb93e636e

An article from Julia DeWahl from 2019—

I served as Chief of Staff to the CEO at Opendoor as we scaled from 200 to 800 employees in a year. Here’s an overview of the role, when and why the role is valuable, and how to make it a success for both the Chief of Staff and the executive.

This post includes 3 parts:

  • Part 1: Overview of the Chief of Staff role
  • Part 2: FAQs for potential Chiefs of Staff
  • Part 3: FAQs for executives considering hiring a Chief of Staff

At an earlier stage company, a Chief of Staff may spend part of their time filling in gaps in the organization, such as working on partnerships when there is no business development team yet, or working on executive recruiting when there are high-priority hiring needs.

At a later stage company, the Chief of Staff may spend more time on internal comms, managing the staff meetings and priorities, and building decision-making frameworks, since larger organizations demand more time and attention on driving alignment.

No matter the stage of the company, a Chief of Staff will also often find themselves setting up or improving systems and processes, and once developed, keeping them at a steady state while moving on to the next set of systems or processes to improve.

What's interesting is, considering my experience, this aligns really well.


A company is typically ready for a Chief of Staff when the company has reached product-market fit and is starting to scale. At this point in a company’s trajectory, internal operations and communications needs become urgent and often this is the time an executive team is just starting to come together.

Aligns with Poet & Scribe's goals, to help companies scale. We were going about it from a company to company perspective, but a better fit would likely be a more individual focus—the C-Suite themselves. As a partner. This could be an interesting thing.


A note on timing: Most Chiefs of Staff have 2–8 years of work experience when entering the role, often from generalist backgrounds. They have learned the basics of how companies operate, how to communicate, how to execute on projects with little oversight, and have developed some “executive presence” that allows them to stand in for their executive as needed.

Aligns with my experience.

Executive Assistants largely focus on the logistics around the executive’s schedule and provide general assistance on tactical items such as travel arrangements. Hiring an Executive Assistant before a Chief of Staff can allow an executive to get immediate tactical support. Once an Executive Assistant is in place, the executive can better evaluate the need for a Chief of Staff.

This is interesting, in terms of an executive assistant is more of a tactical higher, and chief of staff is more strategic...yet operational. Feels like it could be a first hire, before even the rest of the C-Suite?

Comes with a slew of resources at the end: