Senior Trial Attorney

Plymouth Rock Assurance Corporation•Boston, MA

2d•Onsite

About The Position

Plymouth Rock Assurance Company is seeking a highly experienced Senior Trial Attorney for its Boston office. The attorney will represent civil defendants across Massachusetts, primarily in Middlesex, Suffolk, Essex, and Norfolk counties, and manage a substantial, high-volume bodily injury caseload involving complex matters in virtual and in-person settings. The role calls for strong litigation skills, strategic case management, and the ability to work independently while contributing to the legal team. The attorney will manage lawsuits referred from Claims, serve as lead trial attorney on matters that may involve significant exposure, and provide legal advice and guidance to Claims on liability, damages, and risk exposure. The position also involves maintaining relationships with clients, claims professionals, and colleagues; keeping Legal Management informed about case strategy and developments; and working proficiently in a paperless environment using litigation management systems and virtual proceedings.

Requirements

JD from an accredited law school.
Active license to practice in Massachusetts.
7+ years of litigation experience, with a strong focus on insurance defense.
Proven ability to independently manage a high-volume caseload with minimal supervision.
Demonstrated leadership, sound judgment, and strategic thinking in complex litigation.
Exceptional written and oral communication skills, with the ability to influence stakeholders.
High level of integrity, professionalism, and accountability.
Strong interpersonal skills and a collaborative mindset.
Deep knowledge of bodily injury, homeowners, PIP, subrogation, and first- and third-party claims.
Strong understanding of unfair and deceptive trade practices claims.
Expertise in Massachusetts rules of civil procedure and evidence.
Advanced legal research skills using Westlaw and similar platforms.
Familiarity with litigation management tools such as TeamConnect.

Responsibilities

Independently manage and analyze complex lawsuits referred from Claims.
Draft answers, motions, and other responsive pleadings.
Serve as lead trial attorney on matters, including cases involving significant exposure and complexity.
Conduct depositions and represent clients at court conferences, arbitrations, motions, and trials.
Build and maintain strong relationships with clients, claims professionals, and internal legal team members.
Provide strategic legal advice, research, and guidance to Claims on liability, damages, and risk exposure.
Exercise independent judgment in file handling while keeping Legal Management informed of case strategy and developments.
Maintain proficiency in a paperless environment, including litigation management systems and virtual proceedings.
Travel throughout Massachusetts as required.

Benefits

4 weeks accrued paid time off and 9 paid national holidays per year.
Free onsite gym at the Boston location.
Tuition reimbursement.
Low-cost health insurance options with excellent coverage, starting on Day 1, including medical, dental, and vision.
Health and wellness program and fitness reimbursements.
Auto and home insurance discounts.
Matching gift opportunities.
Annual 401(k) employer contribution of up to 7.5% of base salary.
Paid family leave options, including paid parental leave.
Professional development resources, including LinkedIn Learning and licensure assistance.
Convenient location directly across from South Station and pre-tax commuter benefits.