The Problem

36 million businesses in America need insurance—it's not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing.

Over 90% of commercial insurance is still human-led. We're building the inverse: 90%+ AI-led, pushing toward the higher 90s. Roughly 60% of what we place is E&S. We do the work end-to-end—intake, placement, bind, service, renewals—at ~1,000 new customers a month and growing.

You can't build that without a real control function. We're hiring our first dedicated compliance leader to build it.

The Thesis

Compliance at an AI-native brokerage is not a brake. It's infrastructure. The companies that win this transition will have institutional-grade control functions wired 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 will end up explaining themselves to 50 state regulators after the fact.

The Compliance Lead is the one 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, safer.

The bar is proactive, not reactive. Catch the issue through the system before it becomes a complaint, an exam, or a fire drill.

The Role

You build and run Harper's compliance program from the ground up. You own producer licensing and market conduct. You own the clearance workflow for every outbound channel, lifecycle sequence, and partner program before it goes live. You own communication-channel policy, DOI complaint intake and escalation, surplus lines tax operations, and the incident-notification playbook. You partner with finance on customer-funds handling. You partner with engineering on wiring clearance gates and licensing checks into the systems operators actually use. You partner directly with the CEO when judgment calls escalate.

You sit at the intersection of Operations, Growth, Finance, and Engineering. You don't write engineering, but you specify it. You don't replace outside counsel, but you decide when to use them and when to decide.

You're willing to own the rule so frontline managers don't have to be the bad guy. "Not cleared yet" comes from you. So does "here's what you need to launch."

This is not a generalist legal role. This is not pure privacy/DPO. This is not big-carrier committee governance. This is a hands-on operator role for someone with deep insurance regulatory experience who has built, rebuilt, owned, or scaled a meaningful compliance function—and who would rather ship a working clearance gate than draft a memo about one.

What You'll Do

Audit the full regulatory surface — 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. Enforcement mechanism with sales and intake leadership. Appointments, DRLP designations, continuing education. Licensing is not optional, and you're the one who makes that real.
Clear growth before it ships — Sign-off workflow for every new outbound channel, list source, lifecycle sequence, dialer, and partner economics. 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, root-cause feedback into the operating teams. Catch problems through systems, not through complaints.
Own incident & examination readiness — Multi-state regulatory notification playbook. Examination response coordination. The runbook exists before the next incident, not after.
Prevent, don't react — Identify regulatory risk before it surfaces as a complaint or exam. Stand up the leading indicators—licensing drift, scrub failure rates, communication-channel hygiene—and act on them weekly.
Engage regulators proactively — Build and maintain working relationships with state DOIs, stamping offices, and surplus lines regulators. Open dialogue ahead of issues, not after them. Position Harper as a known, credible operator in every jurisdiction we touch.
Instrument the program — Single clearance register. Licensing dashboard by state and producer. Open DOI items, scrub pass rates, time-to-clearance. Weekly review with the CEO.
Use counsel surgically — Outside regulatory counsel for judgment calls, not for basic discovery. You know when to escalate and when to decide.

You Might Be a Fit If…

You've built, rebuilt, owned, or scaled a significant compliance function—not just maintained one at a mature carrier
E&S and surplus lines is 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 to receive a letter.
You're an operator first, lawyer-adjacent second
You take the friction so operators don't have to. You're comfortable owning "not cleared yet" so sales and growth leads aren't improvising on regulatory gray areas.
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 manage outside counsel efficiently and know exactly when to use them
You earn trust quickly with a founder. Low ego, high judgment, fast to action.

Backgrounds That Could Work

Strong candidates might come from compliance leadership at a brokerage or MGA (E&S preferred), regulatory affairs at a carrier with significant surplus lines exposure, a fintech or insurtech control function with multi-state licensing and TCPA depth, a financial-services control function paired with insurance regulatory experience, or outside regulatory counsel ready to step into the operator seat.

The exact title matters less than the ability to walk in, audit the surface, consolidate fragmented controls, ship gates that hold, and instrument the program weekly.

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 meaningful compliance function (or a material part of one)
Hands-on with TCPA, CAN-SPAM, state telemarketing rules, and high-volume outbound enforcement
Experience with DOI complaints, market conduct exams, and E&O posture
Track record of proactive regulator engagement—working with state DOIs and surplus lines authorities before issues arise, not just after
Comfortable working directly with a founder/CEO and earning trust quickly
Strong written communication; you write policies people read once and follow
Bias to ship, low ego, high judgment

Nice to Have

Surplus lines tax, premium finance, and FBO/trust account familiarity
Financial-services or fintech control-function background paired with insurance regulatory depth
Experience clearing dataset-driven outbound (public-records, license lists, DPPA-covered data)
Experience setting guardrails for AI-assisted customer communications
Multi-state incident notification experience
SOC 2 or security-compliance coordination
Anti-rebating, RESPA lane analysis, and partner/referral economics review

Compensation

Salary: $150,000–$220,000 + performance bonuses & equity
Location: San Francisco Bay Area preferred; remote considered for the right candidate—either way, you're embedded with the teams you're protecting
Schedule: Monday–Friday. The hours are long. The people who thrive here wouldn't have it any other way.

Benefits

Health, dental, and vision insurance
Commuter benefits (SF) or remote-work stipend
Team meals and snacks (SF)

Compliance Lead