Senior Trial Attorney

Plymouth Rock Assurance•Boston, MA
•$116,000 - $155,500•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 throughout Massachusetts, primarily in Middlesex, Suffolk, Essex, and Norfolk counties. The role involves managing a substantial, high-volume bodily injury caseload, including complex matters and cases with significant exposure, in both virtual and in-person settings. The attorney independently manages lawsuits referred from Claims, develops case strategy, prepares pleadings and motions, conducts depositions, and represents clients at conferences, arbitrations, motions, and trials. The role also provides legal advice and guidance to Claims on liability, damages, and risk exposure, while maintaining strong relationships with clients, claims professionals, and colleagues. The position works in a paperless environment using litigation management systems and virtual proceedings.

Requirements

  • 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.
  • 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.
  • 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 and 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.

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 coverage beginning 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.
  • Pre-tax commuter benefits.

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What This Job Offers

Job Type

Full-time

Career Level

Senior

Education Level

Ph.D. or professional degree

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