Vice President, Casualty Claims

Plymouth Rock Assurance•Boston, MA

7d•$250,000 - $340,000•Onsite

About The Position

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.

Requirements

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.

Responsibilities

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.

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