Insurance Regulatory Counsel

Oakleaf Partnership
Boston, MA

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.
Find out if this opportunity is a good fit by reading all of the information that follows below.

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, xrczosw 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
Posted 2026-06-18

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