General Counsel - U.S. & Bermuda Insurance Operations

Markel•Chicago, IL

9d•Hybrid

About The Position

If you’re looking for a place where you can make a meaningful difference, you’ve found it. The work we do at Markel gives people the confidence to move forward and seize opportunities, and you’ll find your fit amongst our global community of optimists and problem-solvers. We’re always pushing each other to go further because we believe that when we realize our potential, we can help others reach theirs. Join us and play your part in something special! Markel Insurance is seeking an accomplished General Counsel to lead legal, regulatory, and compliance functions across its U.S. and Bermuda insurance operations. The candidate should have significant in-house expertise and experience with P&C insurance carriers that have both admitted and surplus lines companies. Reporting to the President of Programs and Solutions, the General Counsel will serve as a trusted strategic advisor to the business, oversee a highly specialized legal and compliance organization, shaping how legal, regulatory, and risk disciplines enable disciplined growth, and operate at the intersection of insurance regulation, reinsurance, and corporate development. This role requires deep insurance regulatory expertise, strong executive presence, and the ability to translate complex legal frameworks into practical, solution‑oriented business advice.

Requirements

10+ years of in‑house legal experience, with significant experience supporting property and casualty insurance operations
Extensive knowledge of U.S. state and national insurance regulatory frameworks, including property and casualty as well as excess & surplus lines.
Proven experience advising on producer agreements, insurance distribution, and complex regulatory matters and market conduct activity.
Significant M & A experience along with reinsurance experience.
Proven leadership experience managing and developing high‑performing legal and compliance teams.
Exceptional legal judgment paired with strong commercial acumen, with demonstrated ability to influence enterprise‑level decision‑making.
Ability to translate complex legal and regulatory concepts into clear, practical, and actionable guidance for business leaders.
Calm, decisive, and thoughtful temperament in high-pressure, fast-moving environments, paired with strong executive presence and effective communication across all levels, geographies, and cultures.
Intellectually curious and self-aware leader who values collaboration, recognizes the limits of personal expertise, and seeks diverse perspectives to drive better outcomes.
Proven ability to lead and sustain change, including advancing legal technology adoption and driving operational improvements that enhance efficiency, scalability, and effectiveness.
Empathetic and agile leader who manages through complexity and change with integrity, fairness, and strong ethical grounding, consistently demonstrating behaviors aligned with the Markel Style.
Demonstrated ability to engage effectively with regulators, boards, and senior stakeholders, building credibility, trust, and long-term relationships.
US Work Authorization required. Markel does not provide visa sponsorship for this position, now or in the future.

Responsibilities

Executive Leadership & Strategy Set legal strategy and governance; lead through regulatory change and organizational evolution.
Build and develop a high-performing legal, regulatory, compliance, and legal operations team across locations.
Drive innovation and legal tech/AI adoption to improve efficiency and scale.
Manage budget and outside counsel spend with discipline and transparency.
Corporate Development and M&A Oversight Lead legal and regulatory support for acquisitions and strategic investments.
Advise senior leadership on M&A strategy, structure, and regulatory approvals through close.
Oversee due diligence, structuring, and documentation; identify and mitigate transaction risk.
Support post-close integration, embedding legal, regulatory, and governance requirements.
Manage outside counsel for quality, efficiency, cost control, and alignment to governance and risk tolerance.
Legal & Regulatory Oversight Provide legal and regulatory leadership across U.S. and Bermuda insurance operations.
Navigate multi-jurisdictional regulation; anticipate change and advise on impact and readiness.
Oversee teams responsible for required regulatory filings and related submissions.
Lead approach to filings, approvals, and examinations; engage with U.S. and international regulators.
Support insurance company board meetings across multiple legal entities.
Compliance & Regulatory Risk Management Oversight Partner with compliance and business leaders to build effective, scalable programs and operating structures.
Oversee regulatory data calls, monitoring, and reporting of compliance risk.
Promote a compliance culture that enables growth while reducing risk.
Support regulatory inquiries, investigations, and market conduct examinations.
Reinsurance Oversight Oversee legal support for assumed, fronted, and ceded reinsurance, including structures and agreements across U.S. and Bermuda.
Enable strategic fronting, ILS, and alternative capital relationships.
Contracting & Commercial Transactions Oversight Oversee negotiation of insurance and commercial agreements (e.g., MGA and program administrator agreements).
Ensure agreements align with company policy, regulatory requirements, and strategic priorities.
Identify and mitigate legal and business risk through pragmatic structuring and negotiation.

Benefits

In keeping with the values of the Markel Style, we strive to support our employees in living their lives to the fullest at home and at work.
We offer competitive benefit programs that help meet our diverse and changing environment as well as support our employees’ needs at all stages of life.
All full-time employees have the option to select from multiple health, dental and vision insurance plan options and optional life, disability, and AD&D insurance.
We also offer a 401(k) with employer match contributions, an Employee Stock Purchase Plan, PTO, corporate holidays and floating holidays, parental leave.

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