Paralegal Supervisor

Plymouth Rock Assurance•Boston, MA

1d•Onsite

About The Position

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.

Requirements

Strong understanding of litigation practices and Massachusetts civil procedures
Excellent organizational, interpersonal, communication, and problem-solving skills
Advanced proficiency in Microsoft Office Suite, including Word, Excel, Outlook, and PowerPoint
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

Nice To Haves

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
Experience supporting in-house counsel or corporate legal departments preferred
Experience with legal case management systems such as Time Matters, TeamConnect, or similar platforms preferred

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

Benefits

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