Senior Trial Attorney

Job Description

Plymouth Rock Assurance Company is seeking a highly experienced Senior Trial Attorney to join our Boston office. This role is ideal for a seasoned litigator with 7+ years of insurance defense experience, able to handle a substantial bodily injury caseload and serve as a key contributor within our legal team. The Senior Attorney will represent civil defendants across Massachusetts, with primary venues in Middlesex, Suffolk, Essex, and Norfolk counties. This position requires strong litigation skills, strategic case management, and the ability to handle a high-volume, complex caseload in both virtual and in-person settings.

Essential Functions & 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.

Subject Matter Expertise

• 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.

Qualifications & Education

• JD from an accredited law school and 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.
• Willingness to travel throughout Massachusetts as required.

Salary Range: ​

The pay range for this position is $116,000 to $155,500 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity.​

Perks & 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 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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Job Details

• Job Type: Regular Full-Time
• Category: Legal - Litigation
• Salaried: Salaried