Compliance Lead

Harper•San Francisco, CA

2d•$150,000 - $220,000•Hybrid

About The Position

The company is seeking its first dedicated Compliance Lead to build and manage its compliance program from the ground up. This role is crucial for establishing institutional-grade control functions within an AI-native brokerage, ensuring the business operates safely and efficiently. The focus is on proactive compliance, building infrastructure that acts as a clearance gate rather than a brake, and integrating controls directly into the operational systems. The Compliance Lead will own key areas such as producer licensing, market conduct, communication policies, and incident response, partnering closely with various departments including Operations, Growth, Finance, and Engineering. This is a hands-on, operator-focused role for someone with deep insurance regulatory experience who prefers building and shipping working solutions over drafting theoretical policies.

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 Haves

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.

Responsibilities

Build and run the company's compliance program from the ground up.
Own producer licensing and market conduct.
Own the clearance workflow for every outbound channel, lifecycle sequence, and partner program before it goes live.
Own communication-channel policy, DOI complaint intake and escalation, surplus lines tax operations, and the incident-notification playbook.
Partner with finance on customer-funds handling.
Partner with engineering on wiring clearance gates and licensing checks into the systems operators actually use.
Partner directly with the CEO when judgment calls escalate.
Audit the full regulatory surface, mapping every channel where regulated activity happens.
Own producer licensing & market conduct, including state licensing matrix, enforcement mechanisms, appointments, DRLP designations, and continuing education.
Implement a sign-off workflow for every new outbound channel, list source, lifecycle sequence, dialer, and partner economics, ensuring compliance with TCPA, state mini-TCPAs, CAN-SPAM, DPPA, license-list usage, anti-rebating, RESPA lanes, and E-SIGN/UETA.
Own surplus lines operations, including tax filings, diligent search, stamping office workflows, and multi-state surplus lines posture.
Set communication & E&O guardrails, including approved-channel policy, messaging guardrails for AI-assisted and human reps, document retention, and call-recording standards.
Run DOI complaint intake & escalation, including triage, response coordination, and root-cause feedback.
Own incident & examination readiness, including multi-state regulatory notification playbook and examination response coordination.
Identify regulatory risk before it surfaces as a complaint or exam and stand up leading indicators.
Build and maintain working relationships with state DOIs, stamping offices, and surplus lines regulators.
Instrument the program by creating dashboards for clearance, licensing, and DOI items.
Use outside regulatory counsel surgically for judgment calls.