Insurance Regulatory Compliance Specialist

Help improve advanced AI systems by applying practical insurance compliance expertise to realistic regulatory and operational scenarios. You will develop and assess work that reflects insurer obligations, market conduct, filings, controls, and regulatory reporting across insurance environments. Key Responsibilities

• Design realistic scenarios covering state insurance requirements, market conduct, rate and form filings, licensing, consumer notices, complaint handling, privacy, reporting, audits, and corrective actions.
• Create compliance assessments, control recommendations, filing checklists, regulatory response plans, monitoring procedures, and remediation summaries.
• Write high-quality reference responses reflecting experienced insurance compliance practice.
• Evaluate AI-generated responses using structured rubrics for regulatory accuracy, operational feasibility, jurisdictional awareness, and appropriate escalation.
• Identify overly broad legal conclusions, missing jurisdictional limitations, insufficient controls, inaccurate reporting obligations, and issues that require counsel review.
• Provide written feedback to support improvements in AI model behavior.
• Participate in onboarding office hours and calibration sessions.

• At least 2 years of professional experience in insurance compliance, regulatory affairs, market conduct, filings, licensing, audit, or risk and controls.
• Understanding of how insurance requirements differ by line of business, product, stakeholder, and jurisdiction.
• Experience interpreting regulatory guidance and translating it into policies, procedures, controls, or operational requirements.
• Ability to distinguish compliance analysis from legal advice and recognize when counsel should be consulted.
• Excellent written communication, disciplined research practices, and strong attention to detail.
• Ability to document the basis, scope, assumptions, and limitations of a compliance conclusion.

• CPCU, CCEP, CHC, LOMA, AHIP, or a comparable designation.
• Experience with an insurance department, market conduct examination, or regulatory audit.
• Experience with rate and form filings, surplus lines, producer licensing, or health plan compliance.
• Experience working across multiple states or federal and state programs.
• Experience designing compliance monitoring or corrective action programs.

• Remote engagement open to candidates located in the United States, Canada, or the United Kingdom.
• Per-task work with a minimum commitment of 20 hours per week, with 40 or more hours per week preferred.
• The role is available to begin immediately.

• $800 per task.

• Applications are reviewed on a rolling basis.