The posting
Harper is an AI-native commercial insurance company in San Francisco. We're not bolting AI onto insurance. We're rebuilding the entire business as software, on a simple bet: turning expert human judgment into compute is one of the largest transitions left to make, and a trillion-dollar industry still run 90% by hand is the place to prove it. We've grown ~100x in the last year and we move at that speed: on-site, in person, long days, very high standards. Almost no one joins Harper for insurance; they join to build the company that replaces how it works.
The role
The Chief of Staff's job is to make sure the whole company actually runs (every team, every commitment, every week) while it grows ~100x. That's more surface area than one person can cover. This role is the second set of hands and the second brain in the Office of the Chief of Staff: the person who brings structure to the chaos and gets the right people organized around what matters most.
You'll learn how the company is run by working right next to the Chief of Staff, then take over more and more of it. On a given day that means sitting in leadership syncs and turning decisions into owners and deadlines; noticing that a handoff between sales and underwriting is quietly breaking and fixing it before anyone escalates; jumping into a queue yourself when a team is underwater; or pulling five people from three teams into a room to land a change by Friday.
This is the closest thing Harper has to a founder's associate seat. You see every part of the business, you sit where decisions get made, and you're accountable for making them real. The difference is that the job is operational, not advisory: you're measured on what got done, not on what you recommended.
What you'll do
- Carry part of the operating load. Take a real share of the day-to-day (priorities, follow-ups, escalations) and own it outright, not as a shadow.
- Find the gaps before they find us. Spot where work is stalling, where ownership is unclear, where a process broke at the last 10x. Diagnose it with data, not vibes.
- Create structure where there isn't any. Take a messy, half-owned problem and give it shape: who owns what, what done looks like, when we check in. Then organize the people around it so the work actually moves.
- Do the work when that's fastest. Pick up the phone, work a backlog, build the model, write the doc. Nothing is beneath the role when it's the bottleneck.
- Orchestrate when it's bigger than you. Run cross-functional initiatives across sales, service, underwriting, carriers, and engineering. Set the plan, name the owners, run the cadence, drive to done.
- Close the loop on every commitment. If leadership decided it, it ships. If it slipped, you knew first and you already know why.
- Build systems so nothing breaks twice. Operating cadences, dashboards, trackers, playbooks, and AI tools (Claude Code, Cursor, agents) that replace the manual parts entirely.
- Take the special projects. New-market launches, org changes, hiring pushes, war rooms: whatever is most urgent that week.
Your first 90 days
- Month 1: Work alongside the Chief of Staff across every function. Own follow-through on leadership commitments. Ship your first fix to a broken process.
- Month 2: Own one cross-functional initiative end to end. Take a recurring operating rhythm fully off the Chief of Staff's plate.
- Month 3: Run part of the company's operating cadence on your own, and bring us a gap we haven't spotted yet, with the fix already moving.
Who you are
- You've spent 2+ years somewhere intense (banking, consulting, PE, a scaling startup, or your own company), and you were the person people handed the hard, messy thing to.
- Raw analytical horsepower, plus the willingness to get your hands dirty. You'll build the model, and you'll also make the 40 calls.
- You create structure naturally. Drop you into a chaotic situation with a group of people, and within a day there's a plan, clear owners, and a rhythm.
- You hold a lot of context at once and don't drop threads. Nothing falls through the cracks on your watch.
- You can get people who don't report to you to move by being clear, credible, and relentless, not by title.
- You'd rather own an outcome than produce a deliverable.
- You want to learn how a company is actually run, from the inside, fast.
Requirements: 2–5 years in a high-intensity analytical or operational role (IB, PE, management consulting, BizOps or Strategy & Ops at a high-growth company, or founding your own company); exceptional written and verbal communication; strong with data and spreadsheets; a track record of organizing people and driving cross-functional work to completion; based in SF or willing to relocate immediately.
Nice to have: insurance, fintech, or regulated-industry experience; prior work directly with a founder, CEO, or Chief of Staff; experience leading or coordinating a team; hands-on with AI or automation tooling.
The honest day-to-day
We'll say it plainly, because "Office of the Chief of Staff" sounds more glamorous than it is:
- A real share of it is chasing. Follow-ups, unblocking, holding people to what they said. Done well, it's the backbone of the company. If that sounds beneath you, this isn't the seat.
- The scope never settles. Your week gets rewritten by whatever broke on Tuesday. If you need a fixed lane and a clean spec, you'll be miserable here.
- You lead without authority. You'll ask senior people to move before you've earned it. You earn it by being right and by doing the work yourself.
- It's banking-analyst intensity, on-site. Mon–Fri, roughly 5 AM–8 PM, in person in San Francisco.
- The ceiling is real. People who are exceptional here go on to run a function, step into a Special Projects Lead seat, grow toward Chief of Staff, or leave to build their own thing, because they've seen how the whole company runs. That payoff is on the other side of the work, not instead of it.
Compensation and logistics
- Salary: $135,000–$165,000 + performance bonuses and equity
- Location: San Francisco, in-office. Based in SF or willing to relocate immediately.
- Schedule: Monday–Friday, very early morning start, in-office 5 days a week.
- Benefits: Uber commuter benefits; breakfast, lunch, and dinner provided; snacks, drinks, and coffee daily; free gym membership; health, dental, and vision insurance.
Process
1. People screen: initial fit and alignment
2. Chief of Staff screen: how you think and how you operate
3. Super day: case exercise and real work with the team
