Insurance Attorney Jobs in Massachusetts (NOW HIRING)

About the Role

We are seeking an experienced insurance attorney to serve as trusted legal advisor to the business on insurance product innovation, design, coverage, product research, and specialty insurance matters across Fortegra’s admitted, surplus lines, and warranty/service contract businesses. This role will partner closely with Underwriting, Product, Regulatory, Reinsurance, Operations and business leadership to advise on complex risk issues, craft and interpret policy and contract language, assess claim and coverage positions, and support the development, distribution and administration of insurance and warranty products.

This is a hands-on insurance and warranty product development and legal construct-focused role for an attorney who understands how insurance products work in practice — from policy language, exclusions, and coverage determinations to state insurance considerations, product structures, claims disputes, and specialty program operations. The ideal candidate brings strong experience advising on specialty insurance claims, warranty/service contract claims, admitted and surplus lines products, and coverage issues involving complex or high-exposure matters.

Key Responsibilities

Product, Underwriting & Regulatory Support

· Research and advise on admitted and surplus lines insurance products, including product structure, permissible coverage features, state-specific considerations or prohibitions, and legal/regulatory risk.

· Partner with Underwriting and Product teams to craft and refine policy forms, endorsements, service contract language, coverage terms, disclosures, and program documentation.

· Provide practical legal guidance on coverage wording, underwriting intent, claims administration implications, and product design for new and existing products.

· Advise business stakeholders on legal issues affecting specialty programs, warranty offerings, ancillary products, and distribution models.

· Help identify and assess legal risks related to product rollout, policy interpretation, claims handling, cancellation of the product offering or distribution agreement, and state insurance requirements.

· Assist with regulatory matters, including market conduct investigations and enforcement actions.

Cross-Functional Business Partnership

· Serve as a key legal partner to Underwriting, Product, Compliance, Reinsurance, Operations, Claims, and executive leadership on complex insurance, product innovation, product design strategies, and coverage/claims matters.

· Collaborate with internal stakeholders on new business and product initiatives to ensure legal considerations related to coverage, administration, sales and marketing, product structure, and regulatory compliance are addressed early.

· Translate legal and regulatory analysis into clear, practical business guidance that supports growth while appropriately managing risk.

· Monitor developments in insurance law, coverage trends, and regulatory changes affecting specialty insurance, surplus lines, warranty/service contract products, and claims practices.

Disputes, Escalations & External Coordination

· Support the management of pre-litigation disputes with distribution partners and proper cancellation of agent program agreements.

· Review and advise on customer escalations, regulatory complaints, and other matters where coverage interpretation or claims handling decisions are at issue.

· Work with outside counsel, claims professionals, and business stakeholders to develop strategy on coverage-sensitive disputes and high-risk matters.

Qualifications

· J.D. from an accredited law school and active bar membership in at least one U.S. jurisdiction.

· 5+ years of experience in insurance law, with meaningful experience in insurance coverage, claims, specialty insurance, warranty/service contracts, or product counseling.

· Experience advising on policy coverage drafting and interpretation, product categorization under State laws, distribution arrangements and disputes, or

complex claims matters in an in-house legal department, insurance carrier, MGA/program business, TPA, or law firm insurance practice.

· Familiarity with admitted and surplus lines insurance products and the legal/regulatory considerations that affect product design and underwriting.

· Experience supporting specialty insurance, ancillary insurance, warranty, service contract, or reimbursement products strongly preferred.

· Ability to advise both on legal risk and practical business implications, especially in a fast-moving insurance environment.

· Strong legal research, issue spotting, drafting, and communication skills, with the ability to work directly with senior business leaders and cross-functional stakeholders.