Job Description

Plymouth Rock is seeking a dynamic senior leader to serve as Vice President of Casualty Claims. This is a high-impact executive role with broad ownership of our Casualty Claims organization, spanning Bodily Injury, No-Fault (PIP), Medical Bill Review, and SIU. You'll set the strategic direction, drive operational excellence, and own the financial performance of a large, multi-disciplined claims team.

This role is ideal for a leader who brings deep technical claims expertise, a bias for data-driven decision-making, and a genuine passion for developing talent and building high-performing organizations.

In this role, you will:

• Define and execute the strategic vision for casualty claims operations, setting the roadmap for process improvement, technology adoption, and talent development.
• Own loss and expense outcomes, partnering with Finance and Actuarial on reserve adequacy, trend analysis, and loss development to drive a best-in-class combined ratio.
• Provide executive-level decision-making authority on high-exposure claims and complex settlements.
• Champion operational excellence through data-driven claims management, rigorous metrics, and continuous process improvement across daily, weekly, monthly, and quarterly reporting cycles.
• Lead cross-functional collaboration with IT, Digital, Legal, Underwriting, Product, and Analytics to enhance scalability, efficiency, and the customer experience.
• Develop and mentor Claims directors and supervisors, building a culture of technical excellence, outstanding service, regulatory compliance, and career growth.
• Ensure full compliance with all applicable regulations, fair claims settlement practices, policies, and procedures.
• Translate operational performance and strategic direction clearly across all levels of the organization from frontline teams to the executive suite.

What you bring:

• Bachelor's degree required; advanced degree or professional designation (CPCU, FCAS, JD, MBA) strongly preferred.
• 15+ years of progressive claims leadership in a P&C insurance environment, with proven ability to lead at regional or national scale, preferably within a $1B+ premium organization.
• A track record of measurably improving loss ratio performance, operational efficiency, and customer outcomes.
• Deep technical fluency in casualty claims combined with the strategic mindset to think beyond the file.
• Strong cross-functional influence skills and executive presence; comfortable operating at the C-suite level.
• A genuine commitment to building great teams and developing the next generation of claims leaders.

Salary Range:

The pay range for this position is $250,000 to $340,000 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity.​

Perks and Benefits:

• 4 weeks accrued paid time off + 9 paid national holidays per year
• Free onsite gym at our Boston Location
• Tuition Reimbursement
• Low cost and excellent coverage health insurance options that start on Day 1 (medical, dental, vision)
• Robust health and wellness program and fitness reimbursements
• Auto and home insurance discounts
• Matching gift opportunities
• Annual 401(k) Employer Contribution (up to 7.5% of your base salary)
• Various Paid Family leave options including Paid Parental Leave
• Resources to promote Professional Development (LinkedIn Learning and licensure assistance)
• Convenient location directly across from South Station and Pre-Tax Commuter Benefits

About the Company

The Plymouth Rock Company and its affiliated group of companies write and manage over $2.3 billion in personal and commercial auto and homeowner’s insurance throughout the Northeast and mid-Atlantic, where we have built an unparalleled reputation for service. We continuously invest in technology, our employees thrive in our empowering environment, and our customers are among the most loyal in the industry. The Plymouth Rock group of companies employs more than 1,900 people and is headquartered in Boston, Massachusetts. Plymouth Rock Assurance Corporation holds an A.M. Best rating of “A-/Excellent”

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