By Palo Alto Staffing · with David Chie · Updated 10 Nov 2026.
Short answer: founders and investors give the chief of staff seat to people who have already proven four things: systems thinking, the ability to influence without a title, enough trust with a principal to ask the right questions, and the ability to execute without hand-holding. The title on your résumé matters far less than evidence of those four. Demand is high. Indeed job postings for chiefs of staff were nearly 90% above pre-pandemic levels in September, and the median advertised salary in the Bay Area is about $175,000 versus about $152,000 nationally (Business Insider, citing Indeed: https://www.businessinsider.com/vinod-khosla-hiring-chief-of-staff-vc-2026-10).
We have spent four decades placing senior executive assistants and chiefs of staff with founders and investors. Here is what the top of this market actually looks for, and how strong candidates get there.
Why is everyone talking about chief of staff roles right now?
Two reasons. First, capital. US venture deal value reached $516 billion in the first three quarters of 2026, roughly 44% above the previous full-year record set in 2021, according to PitchBook data reported by Business Insider (https://www.businessinsider.com/vinod-khosla-hiring-chief-of-staff-vc-2026-10). When founders raise large rounds fast, they need someone to run the parts of the company they cannot personally touch.
Second, visibility. In October, one of Silicon Valley's best-known venture investors posted his chief of staff search in public. The posting asked for in-person work in Menlo Park, generally 8 a.m. to 8 p.m., a three-year commitment, and said plainly that the job is "not a dedicated investing seat or a guaranteed path to one" (https://www.businessinsider.com/vinod-khosla-hiring-chief-of-staff-vc-2026-10). That is an unusually honest description of what these jobs are. Read it closely if you want one.
What does a chief of staff to a founder or investor actually do?
It depends on the principal, and that is the first thing candidates get wrong. There are three distinct seats that share one title:
- Chief of staff to a founder-CEO. You run the operating cadence: leadership meetings, board prep, cross-functional projects, the decisions the CEO should not have to make twice.
- Chief of staff to an investor. You help evaluate opportunities, meet founders, research markets, and support portfolio companies. Over time you lead conversations on the principal's behalf. The investor posting above describes exactly this.
- Chief of staff to a family office principal. You manage the family's affairs, often in place of a CEO in a young family office: finances, banking relationships, concierge services, and household staff (Heidrick & Struggles: https://www.heidrick.com/en/perspectives/financial-services/structuring-your-family-office).
The common thread is delegated judgment. A senior EA protects a principal's time and access. A chief of staff makes decisions in the principal's name. If you want to understand where your current role sits on that line, our guide on executive assistant vs chief of staff lays it out: https://www.paloaltostaffing.com/executive-assistant-vs-chief-of-staff
What does a chief of staff earn in 2026?
Pay varies widely with the principal and the mandate. Salary.com puts the average chief of staff to a CEO at $210,000 as of November 1, 2026, with the middle half earning $180,100 to $236,200 (https://www.salary.com/research/salary/alternate/chief-of-staff-to-ceo-salary). Fortune reported in August that some roles in technology and finance reach $400,000 or more (https://fortune.com/article/400k-salaries-direct-line-ceo-chief-of-staff-roles-csuite-springboard/). Equity and bonus matter more at startups. At family offices, total package and stability often matter more.
My advice: do not chase the number. Chase proof of the four things principals pay for. A chief of staff who can design the system, move people who don't report to them, ask the question the principal hasn't thought of, and finish without being chased will find the pay follows. A seat with the wrong principal ends in 12 months, and that line on your résumé is hard to explain.
Who gets hired: the four things principals screen for
When serious principals interview chief of staff candidates, they are testing for four things, whether they say so or not.
1. Proven systems thinking. Principals want someone who fixes the machine, not just the incident. Show a recurring process you redesigned, such as board prep, hiring or the weekly operating cadence, and what changed because of it.
2. Influence without a title. Much of the job is moving people who don't report to you: executives, partners, portfolio founders. Bring an example where you changed a decision or a deadline through credibility alone.
3. Trust to ask the right questions. The best chiefs of staff ask the question the principal hasn't asked yet, and the principal welcomes it. The investor posting put it directly: what matters is how quickly you learn, the questions you ask, and whether you think from first principles. Expect a work sample or case.
4. Execution without hand-holding. Principals hire a chief of staff so they have fewer things to follow up on. "Ran the offsite" is weak. "Chose the venue, cut the agenda from three days to two, and told two partners no" is strong.
Behind all four sits one question I ask about every candidate before I introduce them: would one of the most successful people in the world trust them enough to delegate their life to them? That trust is earned with the correct balance of IQ and EQ to operate efficiently and with humility. The biggest red flag I see is high ego. Humility matters as much as capability.
Can an executive assistant become a chief of staff?
Yes, but it is the harder path, and I would rather you hear that from me. When we studied this, EAs converted into chief of staff seats less often than strong operators with business school backgrounds. The reason is not talent. Candidates who work really well with operators often don't work in environments where they need to be the operator. They are used to being reactive and task-oriented, so when they are asked to look at the bigger picture and prioritize in a commercial context, it can be challenging. Supporting an operator is not the same as being one.
The EAs who do make the move have already built proof of the four things above, and their principal is willing to redefine the role, not just the title. If that is your goal, start owning outcomes now. Take one project end to end. Write the memo. Run the meeting your principal skips. My advice for EAs who want a bigger seat is short: lean into AI and study systems thinking. We wrote about the transition in detail here: https://www.paloaltostaffing.com/post/executive-assistant-chief-of-staff-transition
How do people actually find these roles?
Mostly through trust. Scott Amenta, founder of Chief of Staff Network, told Forbes that most of these roles are filled through warm introductions, and a mentor can vouch for you in a way an application cannot (https://www.forbes.com/sites/edwardsegal/article/how-to-become-chief-of-staff/). At the family office and UHNW level, that is even more true. Many searches are confidential and never posted.
A recruiter who works at this level can tell you honestly whether a seat matches your background, or whether it is a senior EA role with a bigger title.
Where does the role lead?
It can lead almost anywhere, but not automatically. A LinkedIn study from March, cited by Business Insider, found that most chiefs of staff stay in the profession when they change jobs. Of their job moves, 3.7% were to founder or cofounder, 2.9% to chief operating officer and 1% to CEO (https://www.businessinsider.com/vinod-khosla-hiring-chief-of-staff-vc-2026-10). Treat the role as a serious job in itself, not a shortcut.
Frequently asked questions
Do I need an MBA to become a chief of staff?
No, but it helps more than most advice admits. In our experience, operators with business school backgrounds convert into chief of staff seats more often than executive assistants do. What principals are buying is the four things above. Business school plus real operating experience is one common way to prove them. It is not the only way.
What is the difference between a chief of staff and an executive assistant?
An executive assistant manages a principal's time, access, and logistics. A chief of staff acts in the principal's name on projects and decisions. Many top roles blend both.
Are chief of staff roles remote?
Some are. The most senior seats with founders and investors are often in person and demanding. Read the posting and ask about hours and travel before you invest in the process.
How long should I stay in a chief of staff role?
Plan on two to three years. Many principals ask for that commitment up front, and a short tenure is hard to explain.
How do I find chief of staff roles that are not posted?
Build relationships with people close to principals, keep a record of outcomes you owned, and work with a recruiter who places at this level.
If you are an operator or senior EA thinking about a chief of staff seat with a founder, investor or family office, I'm always glad to compare notes: https://www.paloaltostaffing.com/job-seekers