Job Description

The Paralegal Supervisor is responsible for overseeing the daily operations and workflow of the Boston in-house legal support team, including supervising paralegals and administrative staff, managing departmental reporting and metrics, and supporting attorneys and claims professionals in a fast-paced legal environment. This role ensures operational efficiency, compliance with departmental procedures, and high-quality legal support while serving as a liaison between legal staff, leadership, and internal business partners.

Essential Functions and Responsibilities

• Supervise and support paralegals and legal administrative staff to ensure productivity, accuracy, and compliance with departmental standards
• Manage daily workflow assignments, monitor deadlines, and ensure timely completion of legal support activities
• Maintain efficient operation of the Legal Department by organizing office procedures and administrative processes
• Run, analyze, and distribute legal operations and metric reports for management and executive leadership
• Interact professionally with Attorneys, Claims Representatives, Paralegals, vendors, and executive leadership
• Develop and conduct training programs to ensure compliance with departmental policies, procedures, and expectations
• Conduct performance evaluations, coaching, and annual goal-setting for assigned staff members
• Assist with onboarding, mentoring, and development of legal support staff
• Prepare correspondence, reports, memoranda, presentations, and other departmental communications
• Coordinate and manage staff meetings and departmental communications
• Maintain vendor accounts and assist with invoice review and accounts payable processing
• Review and approve office supply requests and assign clerical and administrative responsibilities as needed
• Support litigation management and assist attorneys with case management and operational needs
• Maintain confidentiality and proper handling of sensitive legal and corporate information

Qualifications and Education

• Bachelor’s degree and/or Paralegal Certificate preferred
• 5+ years of paralegal, litigation support, legal operations, or insurance defense experience preferred
• Prior supervisory or leadership experience preferred
• Strong understanding of litigation practices and Massachusetts civil procedures
• Experience supporting in-house counsel or corporate legal departments preferred
• Excellent organizational, interpersonal, communication, and problem-solving skills
• Advanced proficiency in Microsoft Office Suite, including Word, Excel, Outlook, and PowerPoint
• Experience with legal case management systems such as Time Matters, TeamConnect, or similar platforms preferred
• Strong analytical skills with attention to detail and accuracy
• Ability to manage multiple priorities, meet deadlines, and adapt to changing business needs
• Professional demeanor with the ability to communicate effectively across all levels of the organization
• Team-oriented with the ability to collaborate and support departmental goals

Salary Range:

The pay range for this position is $85,000- $115,000 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity.

Benefits & Perks:

• Paid time off
• Free onsite gym at our Boston location
• Tuition reimbursement
• Low cost and excellent health insurance coverage options that start on Day 1 (medical, dental, vision)
• Robust health and wellness programs
• Auto and home insurance discounts
• Matching donation opportunities
• Annual 401(k) employer contribution
• Various Paid Family leave options including Paid Parental Leave
• Resources to promote professional development
• Convenient locations 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”.