The short version
If you are hoping to manage someone else’s diary, this is not your role. If you want to sit beside a CEO, own the work that nobody else owns and help turn a fast-moving AI start-up into a company that runs on rhythm rather than adrenaline, read on.
A seed-stage AI company in San Francisco is hiring its first Chief of Staff. Base salary up to $235K plus meaningful equity. Five days a week in person at a central San Francisco office. Existing US work authorisation required.
Why this company
The business builds testing and reliability tooling for conversational AI: the layer that tells a company whether its AI agents will actually hold up once real customers start talking to them. Every enterprise that puts an AI agent in front of the public needs that answer, and that is fast becoming most enterprises.
The numbers are unusual for a company barely a year old:
- Seven-figure revenue, reached inside its first year
- Customers include some of the largest technology, healthcare and financial services brands in the world
- Millions of conversations processed every month, at real production scale
- Backed by tier-one venture investors and a leading accelerator
- Founded by two young engineers who left big tech to build it, and who still write a lot of the code
The team is under ten people. Whoever takes this seat will shape how the company operates for years, not just how it gets through next quarter.
What you will actually do
You will be the CEO’s second pair of hands and, over time, a second brain. Day to day, that looks like:
- Owning the operating rhythm. Company goals, the metrics that track them, weekly syncs, reviews and planning cycles. If something repeats, you build the system that runs it.
- Running fundraising preparation. The data room, investor updates, board material, the model and the narrative. When the next raise comes around, you make sure the company is ready before anyone has to ask.
- Keeping the numbers honest. One trusted source of truth for revenue, usage, pipeline and burn that the founders and board can rely on.
- Driving hiring. Building the hiring plan, running searches, coordinating interview loops and helping close candidates alongside the founders.
- Leading special projects end to end. Go-to-market experiments, product operations, finance, partnerships. Some will be strategic, some will be messy, and all of them will matter.
- Linking the whole company together. You sit between engineering, product and the commercial team, catching friction early and fixing it before it turns into a problem.
Expect the brief to shift every quarter. The role grows with you, and the ceiling is set by how much you take on.
A week in the seat
Monday you might be rebuilding the revenue forecast after a big customer expands. Tuesday you are running two interview loops and writing up a recommendation on a pricing change. Wednesday you are untangling a customer escalation with the engineering team. Thursday is the investor update and the first draft of next month’s board pack. Friday you are closing out the week’s open items and resetting goals for the next one. No two weeks look the same, and that is the point.
What they want
This is a founding-level seat, so the bar is high and specific.
- Three or more years in a high-output, high-ownership environment. Strong backgrounds include investment banking, top-tier management consulting, venture or growth investing, an MBA from a leading program, or real operating experience as a Chief of Staff or early start-up operator.
- A pedigree you can point to. A top-tier firm, a well-regarded start-up, or a career where you clearly outperformed the people around you.
- Extreme ownership. You spot a problem, take it on and carry it all the way through to resolution without being reminded.
- Organisation bordering on obsessive. You keep a running list, and unfinished business nags at you until it is done.
- Sharp written thinking. You can take a messy, open question, research it, land on a point of view and turn it into a crisp written recommendation people can act on.
- Range. You are as comfortable building a financial model as you are sorting out a customer problem or drafting investor material, often on the same afternoon.
- Real curiosity about AI. You do not need to be an engineer, but you should be able to talk credibly about AI agents, how they are evaluated and how they are monitored in production, and you should want to go much deeper.
Big pluses
- You have founded a company, or been one of the first handful of hires at an early-stage start-up
- You have built processes or systems from nothing and enjoyed every minute of it
- You have worked directly alongside a founder or senior executive and know how to make their week lighter
- Consulting experience where you learned to structure problems and deliver under real pressure
What they do not want
Being clear about this saves everyone time.
- Executive assistants or calendar managers. If your experience is mainly scheduling, travel and inbox management, this is not the right fit, however good you are at it.
- Careers without a top-tier anchor. The founders want evidence you have been held to a very high bar somewhere.
- Remote or hybrid seekers. This is five days in person in San Francisco, with the team.
- People who need a fixed job description. The work is ambiguous by design and changes as the company grows.
- Advisers rather than doers. Strategy work is part of the job, but so is rolling up your sleeves and fixing the thing yourself.
- Big company process lovers. If you rely on layers of approval and a large team around you, a sub-ten person start-up will frustrate you.
- Anyone needing visa sponsorship. The company cannot sponsor, so you need existing, unrestricted work rights in the US.
The package
- Base salary up to $235K, depending on experience
- Equity in a fast-growing, revenue-generating AI company
- Health insurance
- 401(k)
- Free lunch in the office
- Gym membership covered when you use it regularly
- Direct reporting line to the CEO
How to apply
Apply with your resume. To stand out, add a short note, three or four lines is plenty, on one thing you took from a mess to a working system: what was broken, what you built and what changed as a result. That one example will tell the founders more than any cover letter.
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