Associate General Counsel

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


Some legal roles keep you at arm's length from the business. This one puts you at the center of it. As MASA's Associate General Counsel, you'll be the General Counsel's right hand on the matters that shape our growth: bringing products to market, building strong relationships with regulators, and steering significant disputes to smart resolutions. If you're a seasoned insurance attorney who gives executives clear, practical advice and enjoys moving between strategy and hands-on work, we'd love to meet you.

About Us

MASA has been a leader in emergency medical transportation insurance since 1974. We're not just a company - we're a close-knit team dedicated to "Protecting families with compassion when others don't." Our professional yet friendly company culture fosters collaboration, innovation, and a clear mission that resonates through every role as we support our expanding base of 2+ million members across the United States and the Caribbean. Learn more at


What You Will Do

Reporting to our General Counsel, you will lead the legal work that powers MASA's products, market access, regulatory relationships, and most significant disputes:

• Take assigned products from design review through multistate filings, objections, approval, and ongoing compliance, and keep a reliable state-by-state view of approvals, commitments, and deadlines so distribution and member service never miss a beat.
• Shape MASA's regulatory and legislative strategy 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, and coordinating licensing and regulator matters for our Caribbean and international operations.
• Serve as the senior legal partner to product, distribution, claims, and operations teams. Join decisions early, explain legal choices in business terms, translate regulatory requirements into steps teams can carry out, and propose workable alternatives when a plan needs to change.
• Own the strategy for assigned litigation, threatened claims, member complaints, and ambulance payment disputes, directing outside counsel on defenses, budgets, and settlement ranges and resolving matters early wherever it makes sense.
• Act as a trusted extension of the General Counsel by handling day-to-day decisions within delegated authority, bringing 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 speed research, multistate comparisons, and drafting, while setting the safeguards that keep confidential and member information protected and every output verified.

What You Bring

• A 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, with the ability to set priorities and stay effective with lean resources.
• The credibility to step into a difficult regulatory or executive conversation, state MASA's position clearly, and hold it under scrutiny, including 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 a solid understanding of governance, confidentiality, and verification, plus familiarity with insurance regulators' guidance on AI such as the NAIC Model Bulletin.
• Bonus points for experience with Caribbean jurisdictions, a background in a membership, subscription, or healthcare services business, or a track record of managing legal professionals and budgets in a growing legal function.

What We Will Provide You

• Competitive base salary, bonuses, and comprehensive employee benefits programs, including medical, dental, and vision insurance with highly rated carriers; a 401(k) program with a company match; paid time off; company-paid short-term disability, long-term disability, and basic life insurance; and a free MASA membership.
• A professional and friendly company culture that supports a clear mission: "Protecting families with compassion when others don't."
• A senior seat working directly alongside the General Counsel, with the flexibility to work remotely anywhere in the U.S. or hybrid in South Florida, and the opportunity to help shape how a growing legal function puts AI to work responsibly.

Why We Think You'll Love This Opportunity

• Your judgment will matter from day one. Business leaders will bring you in early, and your advice will directly shape the products that protect more than 2 million members.
• You'll get real variety, moving between regulatory strategy, product launches, dispute resolution, and international operations across the U.S. and the Caribbean.
• You'll help build what comes next, from stronger regulator relationships to smarter legal workflows, at a company whose mission you can feel good about.

NOTE: Any pay range listed for this position is an estimate by the job board and may not reflect the actual compensation.


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