Associate General Counsel

Overview

This is a full-time remote position open to candidates across the U.S., or a hybrid position based in South Florida.

The organization is seeking an Associate General Counsel who will work closely with the General Counsel to support growth-driving legal matters, including product development and market access, regulatory relationships, and significant dispute resolution. The role is well-suited for an experienced insurance attorney who provides clear, practical advice to executives and enjoys balancing strategy with hands-on work.

Responsibilities

• Lead assigned product legal work from design review through multistate filings, objections, approval, and ongoing compliance; maintain a reliable state-by-state view of approvals, commitments, and deadlines to support distribution and member service.
• Drive regulatory and legislative strategy in partnership with the General Counsel by:
  • Leading responses to department of insurance inquiries, exams, and enforcement threats
  • Building briefing materials for leadership, lobbyists, and trade associations
  • Coordinating licensing and regulator matters for Caribbean and international operations
• Serve as the 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, including directing outside counsel on defenses, budgets, and settlement ranges and resolving matters early when appropriate.
• Act as an extension of the General Counsel by making day-to-day decisions within delegated authority, providing decision-ready recommendations on material issues, and coordinating and coaching the legal team on assigned matters.
• Help build a modern, AI-enabled legal function by using approved tools to accelerate legal research, multistate comparisons, and drafting, while establishing 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 balancing legal risk against commercial priorities; able to set priorities and remain effective with lean resources.
• Credibility to step into difficult regulatory or executive conversations, clearly state positions, and withstand 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 including healthcare-related regulatory, consumer, claims, or payment matters).
• Practical, hands-on use of AI in legal work, grounded in 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, bonuses, and comprehensive employee benefits programs, including medical, dental, and vision insurance with highly rated carriers.
• 401(k) program with a company match.
• Paid time off.
• Company-paid short-term disability, long-term disability, and basic life insurance.
• Free membership.

Location

• Full-time remote (U.S.); or hybrid based in South Florida.