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Insurance Regulatory Counsel

Job

Oakleaf Partnership

Remote

Full-Time

Posted 4 weeks ago (Updated 2 weeks ago) • Actively hiring

Expires 6/5/2026

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Job Description

Insurance Regulatory Counsel at Oakleaf Partnership Insurance Regulatory Counsel at Oakleaf Partnership in Winthrop, Massachusetts Posted in 11 days ago.
Type:
full-time
Job Description:
We are partnering with a leading global organization seeking an experienced Insurance Regulatory Attorney to support its U.S. Property & Casualty business. This role sits at the intersection of legal, compliance, and business strategy, offering exposure to high-impact transactions, regulatory matters, and day-to-day advisory work. This is a highly visible, collaborative position suited for a proactive and intellectually curious attorney who enjoys working across a wide range of initiatives while serving as a trusted advisor to internal stakeholders. Key Responsibilities Draft and review regulatory filings in connection with corporate and strategic transactions (including holding company matters) Serve as a key point of contact with state insurance regulators and external stakeholders Provide legal support on regulatory inquiries, consumer complaints, and financial/market conduct examinations Monitor and interpret developments in U.S. insurance laws and regulatory activity Deliver practical, business-oriented legal guidance to internal clients across multiple functions Partner closely with colleagues in Legal, Compliance, and other control groups to ensure alignment and risk mitigation Qualifications 4+ years of experience within a top law firm or in-house legal department, with a focus on the insurance industry Strong background in Property & Casualty insurance is required Demonstrated ability to analyze complex legal issues and develop thoughtful, strategic solutions Experience drafting, reviewing, and negotiating agreements and regulatory documentation Excellent written and verbal communication skills Highly organized with strong project management capabilities and attention to detail Ability to work both independently and collaboratively in a fast-paced environment Sound judgment with a practical approach to risk assessment and legal advice Juris Doctor (JD) required; active bar membership in at least one U.S. state This is a hybrid position 4 days in office 1 day WFH

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