Hybrid Staff Attorney at Plymouth Rock Company

Are you a litigation-savvy attorney ready to make a meaningful impact—without the pressure of billable hours?

Join our collaborative in-house legal team, where your work directly supports insured clients and helps shape legal strategy across the company. We are seeking a Staff Attorney to represent both insureds and the company in a broad range of legal matters, including litigation, arbitration, and claims support.

This is a unique opportunity to apply your litigation skills in a role that values strategic thinking, collaboration, and balance—without the demands of traditional law firm life.

Responsibilities:

• Represent insured clients in Superior Court litigation from case inception through trial or settlement.
• Handle uninsured/underinsured arbitrations, subrogation matters, and small claims hearings.
• Provide legal counsel and strategic support to claims management and internal teams.
• Take depositions, draft legal memoranda and motions, and argue cases in court.
• Represent the company in appeals when necessary.
• Guide claims personnel through mediation and arbitration processes.
• Conduct examinations under oath and participate in litigation roundtable sessions.
• Train and advise staff on legal procedures, case law, and best practices.

Qualifications:

• JD and license to practice in Connecticut.
• Minimum of 3 years of litigation experience, preferably in insurance defense or related practice.
• Strong analytical skills with expertise in liability, coverage, and damages evaluation.
• High integrity and a results-oriented mindset.
• Proven ability to influence, collaborate, and communicate across legal and non-legal teams.
• Experience working independently and managing a varied caseload.
• Willingness to travel within Connecticut for court appearances and hearings.
• Experience with arbitration forums and small claims litigation.
• Prior in-house counsel or insurance industry experience.
• A passion for mentorship and legal education within teams.

Salary Range: The pay range for this position is $93,500 to $120,500 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity.​

About the Company

The Plymouth Rock Company and its affiliated group of companies write and manage over $2 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”