Compliance Lead

About this role

COMPLIANCE LEAD

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

We're rebuilding a brokerage to run 90%+ AI-led - intake, placement, bind, service, renewals, end to end, at ~1,000 new customers a month, roughly 60% of it E&S. You can't move a regulated business that fast without a real control function underneath it. We're hiring our first dedicated compliance leader to build that function from scratch.

At an AI-native brokerage, compliance is not a brake - it's infrastructure. The companies that win this transition wire institutional-grade controls into how the business actually runs: clearance gates, licensing matrices, communication policies, and incident playbooks that operators trust and ship against. The ones that don't end up explaining themselves to 50 state regulators after the fact.

You're the person who builds that infrastructure: audit first, consolidate what's fragmented, gate what's high-risk, instrument what matters, partner with engineering on the rails. Then the company moves faster and safer. The bar is proactive, not reactive - catch the issue through the system before it becomes a complaint, an exam, or a fire drill.

You report directly to the CEO and sit at the intersection of Operations, Growth, Finance, and Engineering. You don't write the engineering, but you specify it. You don't replace outside counsel, but you decide when to use them and when to just decide. And you own the rule so frontline managers don't have to be the bad guy - "not cleared yet" comes from you, and so does "here's what you need to launch."

What this role is not: it's not a generalist legal seat, it's not pure privacy/DPO, and it's not big-carrier committee governance. It's a hands-on operator role for someone with deep insurance regulatory depth who'd rather ship a working clearance gate than draft a memo about one.

WHAT YOU'LL DO

- Audit the full regulatory surface first. Map every channel where regulated activity happens - channels, lists, sequences, licensing matrix, open complaint exposure. No new policies until you know what's live.

- Own producer licensing & market conduct. State licensing matrix by producer and authority level, with a real enforcement mechanism alongside sales and intake leadership. Appointments, DRLP designations, continuing education. You're the one who makes "licensing is not optional" real.

- Clear growth before it ships. A sign-off workflow for every new outbound channel, list source, lifecycle sequence, dialer, and partner economic - TCPA, state mini-TCPAs, CAN-SPAM, DPPA, license-list usage, anti-rebating, RESPA lanes, E-SIGN/UETA. Default-deny on gray areas; ship clearance on the cleared ones.

- Own surplus lines operations. Tax filings, diligent search, stamping-office workflows, multi-state surplus lines posture.

- Set communication & E&O guardrails. Approved-channel policy; claims, cancellation-save, and renewal-messaging guardrails for both AI-assisted and human reps; document retention and call-recording standards.

- Run DOI complaint intake & escalation. Triage, response coordination, and root-cause feedback into the operating teams. Catch problems through systems, not through complaints.

- Own incident & examination readiness. A multi-state regulatory notification playbook and exam-response coordination - the runbook exists before the next incident, not after.

- Engage regulators proactively. Build working relationships with state DOIs, stamping offices, and surplus lines regulators. Open dialogue ahead of issues, not after. Make Harper a known, credible operator in every jurisdiction we touch.

- Instrument the program. One clearance register. A licensing dashboard by state and producer. Open DOI items, scrub pass rates, time-to-clearance — reviewed weekly with the CEO.

- Use counsel surgically. Outside regulatory counsel for judgment calls, not basic discovery. You know when to escalate and when to decide.

WHO YOU ARE

- You've built, rebuilt, owned, or scaled a meaningful compliance function — not just maintained one at a mature carrier.

- E&S and surplus lines are in your bones - diligent search, tax, stamping offices, state-by-state quirks.

- You write policies people actually follow and build sign-off workflows that don't kill velocity.

- You're proactive by instinct. You'd rather instrument a leading indicator than respond to a complaint, and you'd rather pick up the phone with a regulator than wait for the letter.

- You're an operator first, lawyer-adjacent second. You think in dashboards, not memos — if you can't answer "what's cleared, what's exposed, who's licensed where" in one view, that's the first thing you build.

- You've cleared high-volume outbound under TCPA and state mini-TCPAs in a real revenue environment.

- You're comfortable with AI-assisted operations and set guardrails for automated comms instead of pretending automation isn't happening.

- You take the friction so operators don't have to - comfortable owning "not cleared yet" so sales and growth aren't improvising on gray areas.

- You earn trust fast with a founder. Low ego, high judgment, bias to ship.

REQUIREMENTS

- 5+ years in insurance compliance, regulatory affairs, or a control function - brokerage or agency experience strongly preferred.

- Multi-state P&C licensing fluency; demonstrated surplus lines experience.

- Track record building, rebuilding, owning, or scaling a…