Forward Deployed Operations

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

A trillion-dollar industry runs on knowledge nobody wrote down — what the data means, what the operation actually needs, what users are motivated by, and where the leverage hides. This role synthesizes those disconnected streams into one thing: a clear read on the most important problem to solve next. Then you build the thing that solves it.

You'll embed with the operators who run Harper — sales, service, underwriting, carrier relations — learn the operation end-to-end, find the 20% of friction causing 80% of the drag, and ship the thing that removes it. One day you're chasing a stalled quote with an underwriter. The next you're shipping the automation that makes sure no quote stalls again. The day after, you're on a customer call, feeding what you heard into a product spec. You run the operation and you improve the operation — both, always. It takes a curious, analytical mind, sharp product intuition, and genuine empathy for the people doing the work.

What you'll do

• Find the leverage. Sit with operators, watch the work, and surface the automations nobody built because nobody knew they were possible yet.

• Run the operation. Underwriter follow-ups, carrier communications, customer calls, keeping deals moving through the pipeline. You're in the work, not above it.

• Build fast. AI agents, internal tools, workflow automations — prototype in days, ship in weeks.

• Instrument everything. Write SQL, pull the data, build the dashboard. Prove what you shipped moved a number — in business terms, not feature terms.

• Shape what gets built next. Translate operational pain into product requirements. The patterns you spot become the things engineering builds next.

• Move where it's urgent. Context-switch across functions based on what matters most this week. Scope doesn't respect org charts here.

Who you are

• You've shipped internal tools or automations end-to-end — not just designed them.

• You've also run real operations: customer-facing, process-heavy, or both. You know what it feels like when a system breaks at 7 AM.

• You measure yourself in business outcomes: "conversion went up 15%," not "the feature shipped."

• You can walk into a room of non-technical operators, explain why a number moved, and have them trust you.

• You'd rather own a messy problem end-to-end than execute a clean task someone handed you.

• You've been exceptional at something before, and you're looking for the place that finally matches your ceiling.

Requirements: 2–4 years in a high-pace environment (startup, operations, consulting, or engineering); a track record of building and shipping things that ran in production — internal tools, automations, workflows; comfortable in SQL and at least one of Python or TypeScript; hands-on with AI coding tools (Cursor, Claude Code, or equivalent), not just aware of them; strong written and verbal communication with both technical and non-technical audiences; based in San Francisco or willing to relocate immediately.

Nice to have: LLMs, AI agents, or voice AI experience; a background in insurance, fintech, or another regulated, high-stakes industry; prior startup or founder experience; solutions engineering, operations, or customer success experience.

The reality

This is on-site in San Francisco, in person, long days, high standards. A real share of the week is follow-ups, chasing, coordination, and cleanup — the operational backbone, done well. The system-building is earned by doing the unglamorous work first.

Ambiguity is the job, not a phase. Scope shifts week to week. If you need a fixed lane and a clean spec, you'll be uncomfortable here.

The ceiling is high and real. People who are exceptional here go on to run functions, lead teams, or start companies — because they've seen how the whole business works. That's the payoff, and it's on the other side of the grind.

Compensation & logistics

• Salary: $125,000–$170,000 depending on experience + performance bonuses & equity

• Location: San Francisco, in-office. Based in SF or willing to relocate.

• Schedule: Monday–Friday, very early morning start, in-office five 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. 15-min founder call — alignment on mission and pace.

2. Technical screen — a real operations and build problem; we want to see how you diagnose and what you'd ship.

3. Super Day on-site — meet the team, sit in on the operation, do real work alongside us.

To apply

Send your resume and tell us about something you built that moved a measurable business number — and a broken process you've fixed. Both matter here.