“The most effective way to do it, is to do it.”
Amelia Earhart
Most Chief of Staff roles are a holding pattern. This one is a launchpad.
A late-stage, venture-backed insurance technology company in San Francisco is creating its first Chief of Staff seat, reporting directly to the founder-CEO. The company is backed by top-tier Silicon Valley investors, well capitalised for years ahead, and at the stage where the core business is proven and growing fast while the next few business lines are still being invented. Around 200 people, a leadership team drawn from some of the strongest scale-ups of the last decade, and a CEO who wants a genuine operating partner rather than a diary manager.
The purpose of the role is explicit: find the person who will eventually own a P&L for a business unit they helped build. Earhart had it right. This is not a role for someone who wants to advise on the doing.
What you will do
Be the CEO’s operating partner from day one. You own the hardest cross-functional problems across multiple business lines, the ones that currently have no clear owner. These are the problems that land on the CEO’s desk because nobody else can claim them: a process that breaks every time the company doubles, a decision stuck between three functions, a new initiative that needs a general manager before it has one. You find the bottleneck, work out the fix, and drive it to an outcome. You sit with the CEO and the business unit leaders, spot patterns, remove blockers and accelerate growth. You travel with the CEO 10 to 30% of the time to other offices and key meetings.
Shape where the company goes next. The business is expanding well beyond its original product into new lines. You pressure-test those opportunities, build the case with real numbers, and potentially quarterback the launch of a new vertical. This is where the path to a P&L begins. The company has designed the role as an incubator: the Chief of Staff who builds something is the Chief of Staff who gets to run it.
Design how the company runs. Business reviews, data and insights cadences, board storytelling, operating rhythms across a business that is about to become much larger. A 200-person company runs on habits. A 600-person company runs on systems. You build the systems before they are needed, and you make the board narrative something the CEO is proud to present.
Build with AI, not just talk about it. The company is AI-native by design and expects its Chief of Staff to be the same. You actively build automations and tools with Claude, Cursor and similar, and you can show what you have shipped. You do not need to be an engineer. You need to be the person who automates the reporting pack over a weekend rather than asking for an analyst on Monday. If you have a workflow, agent or internal tool you built because it annoyed you that nobody else had, that is exactly the instinct this CEO is hiring for.
Your first six months, roughly
Month one, you are in every meeting that matters and you say less than you think. Month two, you have picked the two problems that cost the company the most and nobody owns, and you own them now. Month three, the operating cadence has your fingerprints on it. By month six, you have a new business line or a major cross-functional initiative with your name against it, numbers that moved because of you, and a clear view of what you would run if the CEO handed you the keys.
Who thrives here
- Six to ten years’ experience in total
- Two or more years at McKinsey, BCG or Bain early in your career. Investment banking or private equity analyst programmes also count
- Followed by real operating experience at a venture-backed startup through its Series B to D scaling phase. You have been inside a company while it doubled, and you know what breaks
- Promoted early and given more scope without changing companies. Your resume shows a company trusting you with more, not a sequence of lateral moves
- Founder DNA. A startup that did not work out counts in your favour, not against you. It means you have already chosen ownership over safety once
- Strong financial modelling. You parse the data and build the model yourself, then make the call
- The executive presence to push back on senior leaders and operate with very little direction. You can walk into an ambiguous situation with no brief, no owner and no deadline, and come out with a plan and a result
- A top-tier MBA is a plus if you took that route, but strong companies on your resume matter more than the degree
- Based in San Francisco, or ready to be. Five days a week in the downtown office, non-negotiable, and you would not want it any other way for a role this close to the CEO
What this role is not
- Not administrative or coordination. The CEO wants a business owner in waiting, not a scheduler. A builder who has never held the Chief of Staff title is a stronger fit than a career Chief of Staff who has held it three times.
- Not a pure consulting seat. MBB alone is not enough. MBB plus a real startup operating chapter is the combination. If every line on your resume is a slide, this will frustrate you.
- Not remote. Five days a week in San Francisco. Relocation support and visa transfers (H-1B, OPT) are available, so the door is open to the right person anywhere in the US. The seat itself does not move.
Why people say yes
Direct partnership with a founder-CEO from day one, in a company where the founder still sets the pace. A credible, stated path to running a business unit rather than a vague promise of growth. A well-funded, fast-growing company with real traction in a market the incumbents have barely touched. Up to USD $300K base plus equity with genuine upside at this stage. Fully paid medical and 401k match. A company that practises the AI-first operating model it talks about, from the CEO down.
A word on the obvious
Yes, insurance. If that word made you pause, consider that the largest, slowest, most profitable industries are exactly where AI-native companies are compounding fastest right now, and that the people building them are the ones who will own the next decade of operating careers. The founders here already know this. They are looking for one more person who does.
How to apply
Send your resume and a short note. Skip the cover letter. Tell us about the best thing you have built or fixed in the last two years, what it was worth to the business, and what you are itching to run next. If you read this and thought “finally,” we would like to hear from you this week.
