The Chief of Staff role in Silicon Valley

Julia DeWahl
Apr 29 · 13 min read

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
Before working at Google and Facebook, Sheryl Sandberg was Chief of Staff to US Treasury Secretary Larry Summers

Part 1: Overview of the Chief of Staff Role

What is a Chief of Staff?

A Chief of Staff is the right-hand person and force-multiplier to an executive, often the CEO. This can mean many things depending on the needs of the company and executive, and can change over time, but typically encompasses managing the executive’s priorities, overseeing staff/internal operations, and spearheading special projects.

Here are a few examples of what a Chief of Staff might work on:

  1. Manage priorities: do calendar audits, review and synthesize metrics/ initiatives to support company priority setting

In addition, the Chief of Staff is often an advisor and confidant to the executive since he or she shares a similar purview to the executive, and doesn’t have their own agenda or separate team and goals like other executives do.

How does the Chief of Staff role vary by company?

The Chief of Staff role will vary based on company stage, company priorities, and the executive, resulting in no two roles that look exactly alike.

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. The Chief of Staff will likely prioritize upleveling areas of the business that are the most cross-functional, and thus where there isn’t naturally a clear owner. Additionally, areas where the executive needs to have a lot of direct input can be a good fit for a Chief of Staff, such as the executive’s monthly company update email or the company All Hands.

When is a company ready for a Chief of Staff?

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. You’ll know its time for a Chief of Staff when an additional individual’s time is not better spent somewhere else in the business, e.g. building product or performing critical supporting roles.

Part 2: FAQs for Potential Chiefs of Staff

President Harry Truman at lunch with John Steelman, the first Chief of Staff to a US President

Should I take on a Chief of Staff position?

It depends on what you’re optimizing for, how the role is scoped, and who the executive is you’d be working for. There are pros and cons to the role to consider before making the leap.

Benefits:

  • Unique perspective across the company: you’ll have a view across the entire company unlike any other role except your executive’s, and may include things like joining board meetings, executive staff meetings, and supporting the vision and strategy setting for the company

Potential drawbacks:

  • Opportunity cost: by choosing to enter the Chief of Staff role, you’re opting out of the learning and growth along the trajectory you’re currently on for the period of time you’re in the Chief of Staff role

If you do decide to move forward in pursuing a Chief of Staff role, the two most important things you can do when engaging with a company and executive on a Chief of Staff role are:

  1. Scope the role: ensure you’ll have impact by clearly defining what the role will entail. Review in detail what your priorities will be, how much time you’ll spend on each, and how you’ll work together on a daily basis. Discuss what success looks like in the role, and how you’ll measure it.

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. You’ll usually see more years of work experience among Chiefs of Staff at larger companies, just like you do in other roles.

What does success look like in the Chief of Staff role?

An excellent Chief of Staff transforms their executive into the best version of themselves.

  1. Manage your executive’s time closely to ensure it is spent on the top priorities for the company. It is your executive’s most scarce and critical resource. This could include weekly calendar audits and a daily standup to sync on priorities.
  • Metrics: Company metrics inevitably evolve over time, so check in here to start. Are these metrics reflective of the priorities of the business? On what cadence and in what setting are they reviewed by the company and by the executive team?

Finally, success in the Chief of Staff role requires trust, both between you and your executive, and you and the rest of the organization. The Chief of Staff is privy to sensitive information that most employees, including other executives, are not. It’s critical not to break that trust by sharing confidential information.

How should I prepare for a Chief of Staff interview?

The Chief of Staff role is largely about fit with (1) the role and (2) the executive. Make sure you understand the scope of the role and have spent time getting to know the executive before evaluating whether or not the opportunity is right for you.

In an interview setting, the executive also wants to get a sense for whether you’ll be a good fit for the role, both in your skills and attributes but also interpersonally. Here are a few questions they might ask:

  1. Why do you want to be a Chief of Staff? You might want to speak to what kind of impact you want to have on the organization, what you want to learn in the role, and how that might prepare you for what you want to do next

You’ll also want to ask some questions of the executive to make sure the role will be a fit for you. Here are a few suggestions:

  1. Why are you hiring a Chief of Staff? It can be helpful to understand the motivations behind the hire.

Got the job! How should I prepare to start?

The best place to reference when preparing to start is the scope of the role you interviewed for. The scope will vary based on your company and executive’s needs, and can change over time — most important is that it’s codified up front. When defining the scope of the Chief of Staff role with Eric Wu, CEO of Opendoor, we broke down responsibilities across 3 areas:

  1. Operations of the office of the CEO, e.g. managing Eric’s time allocation, weekly staff meeting, and quarterly/annual planning

Like any new job, a good place to tactically get started is by preparing a 30–60–90 day plan based on the priorities of your executive. You’ll also want to define how you’ll work together, though this will likely evolve over time. Eric and I had a daily 10am standup that included his Executive Assistant where we’d review his calendar and the day’s key objectives for each of us, and a weekly 30 minute 1:1.

What should I do after the Chief of Staff role?

Most people see Chief of Staff roles as a 1–2 year tour of duty followed by a transition back into the organization. However, there have been excellent Chiefs of Staff who have stayed in the role for many years and play incredibly impactful roles, so that’s an option as well. Make sure you address timeline and what you might want to do next with your executive before kicking off in the role, and check in on this topic periodically. Since many Chiefs of Staff come from generalist backgrounds, their next role is likely a generalist role at a more senior level in the organization or working on a new business unit or product.

Part 3: FAQs for Executives

Should I hire a Chief of Staff?

There are good reasons to hire a Chief of Staff and bad reasons to hire a Chief of Staff.

Good reasons include:

  1. You want to get leverage on the things you do today that help you better understand the business, manage your team, and make decisions, and you’ve already leveraged your direct reports on these fronts but still have additional needs.

Bad reasons include:

  1. You’re exhausted and just want someone to take the reins.

How is a Chief of Staff different than an Executive Assistant?

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. Some executives hire Chiefs of Staff and scope the role to include tasks which are typical of an Executive Assistant. I recommend against this, as the profile of the person who will join as a Chief of Staff role that includes assistant tasks will be different, and the executive may not get the leverage they need on more strategic projects.

Who should I hire for my Chief of Staff?

You will have most success by hiring someone who is a high horsepower, trustworthy, is a good communicator, has executive presence so they can interface well with external parties, at your board meeting, and with your executive team, and who is a fit with you personally.

You will likely have the option of hiring internally for the Chief of Staff role, or externally. If hiring externally, usually the reason to do this is if you want someone who has been a Chief of Staff before, or if there isn’t someone internally who would be a good fit. Otherwise, hiring internally has many benefits, including your ability to better assess them based on their history at the company, and their preexisting understanding of the business and culture which will help them hit the ground running much faster.

How should I run the interview process?

Like most interview processes, you’ll want to start by identifying what traits and skills you want to see in that person. Since each executive and company has slightly different needs, this may vary, but overall I’d test for the following:

  1. Raw horsepower and problem solving skills: you might ask the candidate to come up with a framework for making a decision, or how they’d prioritize resources among a few projects at the company (this works better when the candidate has company context).

How should I make the most of working with a Chief of Staff?

Like any other direct report, alignment and accountability are critical. Create a role scope document that outlines the areas of responsibility, such as Internal Operations, Internal Comms and Special Projects, and establish quarterly goals within each of these buckets. Set expectations together about how much time is spent on each bucket, and on how you expect to receive updates. I used to send Eric a weekly update email with 3 categories — Completed, Upcoming/In Progress, and Blockers (otherwise known as the 3 P’s — Plans, Progress, Problems). We would then use our 1:1 time to discuss blockers and any other areas I needed him input on. We would also ensure feedback (both ways!) was part of our weekly 1:1s.

Additionally, you’ll need to share what you’re thinking about frequently and openly, so that your Chief of Staff has sufficient context to do their job well. This may be new and feel uncomfortable at first, but provided you have a trusting relationship, this will enable your Chief of Staff to be a useful sounding board.

That’s all for now! Let me know if you have feedback or questions @juliadewahl on Twitter. In the meantime, here are some resources for additional reading:

Thanks to Chiefs of Staff Andrew Schulte (Opendoor), Anuj Abrol (Atrium), and Carly Emmer (Coinbase) for their feedback on this post.

COS TECH FORUM

We are a collective group of operators serving a unique function of our respective businesses; the Chief of Staff. Join us as we share stories, lessons, thoughts and ideas of the COS role and challenges faced building technology companies from the ground up.

Julia DeWahl

Written by

Angel investor. Formerly Opendoor and Bain. Loves skiing and dinner parties.

COS TECH FORUM

We are a collective group of operators serving a unique function of our respective businesses; the Chief of Staff. Join us as we share stories, lessons, thoughts and ideas of the COS role and challenges faced building technology companies from the ground up.