Associate General Counsel

Overview

This full-time role is available as a remote position across the U.S., or a hybrid position based in South Florida.

The Associate General Counsel will serve as the General Counsel’s right hand on legal matters that support product growth, regulatory relationships, market access, and major disputes. This position emphasizes clear, practical legal advice to executives, with a balance of strategic oversight and hands-on execution.

Responsibilities

• Manage assigned products from design review through multistate filings, including objections, approval, and ongoing compliance; maintain a reliable state-by-state view of approvals, commitments, and deadlines.
• Support regulatory and legislative strategy with the General Counsel by leading responses to department of insurance inquiries, exams, and enforcement threats; build briefing materials for leadership, lobbyists, and trade associations; coordinate licensing and regulator matters for Caribbean and international operations.
• Act as a senior legal partner to product, distribution, claims, and operations teams by joining decisions early, explaining legal choices in business terms, translating regulatory requirements into actionable steps, and proposing workable alternatives when plans change.
• Own strategy for assigned litigation, threatened claims, member complaints, and ambulance payment disputes; direct outside counsel on defenses, budgets, and settlement ranges; resolve matters early where appropriate.
• Handle day-to-day decisions within delegated authority; provide decision-ready recommendations on material issues; coordinate and coach the legal team on assigned matters.
• Help build a modern, AI-enabled legal function by using approved tools to improve research, multistate comparisons, and drafting, while setting safeguards to protect confidential and member information and ensuring every output is verified.

Requirements

• J.D. and an active license in at least one U.S. jurisdiction.
• 8+ years of progressive legal experience with substantial insurance regulatory work, including ownership of multistate product filings from submission through approval and implementation.
• Significant in-house experience at an insurance carrier, MGA, healthcare company, or other regulated business, advising executives directly and weighing legal risk against commercial priorities; ability to set priorities and remain effective with lean resources.
• Credibility to lead difficult regulatory or executive conversations, clearly state positions, and hold them under scrutiny with state regulators, legislators, and organizations such as the NAIC and NCOIL.
• Experience managing outside counsel in litigation or disputes, evaluating exposure, and advising on resolution, ideally alongside healthcare-related regulatory, consumer, claims, or payment matters.
• Practical, hands-on use of AI in legal work, grounded in knowledge of governance, confidentiality, and verification; familiarity with insurance regulators’ guidance on AI such as the NAIC Model Bulletin.

Preferred Qualifications

• Experience with Caribbean jurisdictions.
• Background in a membership, subscription, or healthcare services business.
• Track record managing legal professionals and budgets in a growing legal function.

Compensation & Benefits

• Competitive base salary and bonuses.
• Comprehensive employee benefits, including medical, dental, and vision insurance with highly rated carriers.
• 401(k) program with company match.
• Paid time off.
• Company-paid short-term disability, long-term disability, and basic life insurance.
• Free membership.

Location

• Remote position open to candidates across the U.S.
• Or hybrid based in South Florida.