Job Description Help for Job Description. Opens a new window. Description We are looking for an experienced, commercially minded attorney to provide interim legal leadership for insurance-regulated offerings, healthcare-related regulatory matters, and international business activities. This Long-term Contract position is REMOTE, and offers the opportunity to advise senior leaders on a wide range of complex legal and compliance issues with a high degree of independence. The role will focus on supporting regulated membership and insurance products, guiding operational teams through state-specific requirements, and helping the organization manage domestic and cross-border legal matters during an interim engagement.

Responsibilities:

• Direct legal strategy for insurance compliance matters across multiple jurisdictions, including product review, regulatory submissions, agency responses, and ongoing adherence to applicable rules.
• Counsel internal teams on state insurance obligations such as notice requirements, disclosures, consent standards, and related operational expectations.
• Provide legal support for the rollout and ongoing administration of insurance products issued through an affiliated carrier structure.
• Work closely with business partners to regulatory obligations into efficient, practical processes that can be implemented across the organization.
• Advise on healthcare-related legal and regulatory issues connected to ambulance services, including complaints, reimbursement disputes, and member-facing concerns.
• Oversee legal needs tied to Caribbean and other international operations, including registrations, renewals, local legal questions, and commercial arrangements with agents or partners.
• Manage coordination with external counsel on active litigation matters and act as the primary connection point between outside advisors and internal stakeholders.

Remote Requirements

• Juris Doctor degree from an accredited law school and an active license to practice law in at least one U.S. jurisdiction.
• Approximately 4 to 7 years of legal experience in insurance regulation, healthcare regulatory law, or a closely related practice area.
• Demonstrated background handling insurance filings, compliance analysis, regulator communications, or similar state-level regulatory work.
• Strong ability to deliver clear, business-focused legal guidance to executives and cross-functional teams.
• Experience addressing healthcare consumer issues, claims-related questions, or regulatory matters is strongly preferred.
• Exposure to international or Caribbean legal matters is advantageous, though not essential.
• Familiarity with overseeing litigation through outside counsel is helpful, even if direct courtroom experience is limited.
• Sound judgment, strong communication skills, and a hands-on approach to managing complex legal work with minimal supervision.

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