Agency Operations Supervisor

The Agency Operations Supervisor leads a skilled team responsible for delivering accurate, compliant, and efficient agency operations support to Plymouth Rock's Independent Agents. In this role, you will manage daily operations, coach and develop team members, and ensure we meet service, quality, and compliance objectives. With deep knowledge of agency onboarding, licensing, state regulatory requirements, and our core systems, you will drive operational excellence, support agency growth, and serve as a key operational partner to the Marketing and our agency network.

RESPONSIBILITIES

Oversee the accurate and timely execution of agency appointments, terminations, modifications, and onboarding activities across all states, ensuring adherence to regulatory requirements and internal standards. Seek opportunities to lower operational costs by ensuring we do not extend licenses disproportional to agency engagement. Monitor agency requests, workload distribution, and service levels while maintaining appropriate staffing to ensure team task completion consistently outperforms the required 3-5 business day standard. Use Quality Assurance data and performance trends to drive accountability, reduce errors, and support continuous improvement. Serve as a subject matter expert in core systems including Agency Data Repository (ADR), Agent Web, and Salesforce and ensure the team has the training, tools, and guidance needed to execute work effectively. Partner with Compliance and Legal to ensure all agent-facing documents, contracts, and communications meet regulatory standards across our 6-state footprint. Lead and contribute to key strategic projects and operational initiatives that strengthen the agency channel, including AARP re-credentialing, mergers and acquisitions support, self-service expansion, and ongoing efforts in process improvement, efficiency gains, and automation; leverage data and performance reporting to identify trends and drive informed decision-making. Serve as a key liaison to internal partners including Marketing, IT, Finance, Direct, Home, and Legal to ensure alignment, issue resolution, and consistent execution. Provide regular reporting on key metrics, performance trends and deliver project status updates and summaries to leadership and key stakeholders. Continuously analyze team workflows to identify inefficiencies and develop improvements that enhance accuracy, productivity, and service delivery. Coach, develop, and motivate team members through regular 1:1s, performance feedback, and individualized development plans that build expertise and support career growth.

QUALIFICATIONS

3+ years of experience in operations or a related field, with a working knowledge of the Independent Agent channel preferred, prior supervisory experience a plus. General understanding of insurance regulatory and compliance requirements across multiple states. Strong technical aptitude and ability to learn new systems quickly; knowledge of database management, policy systems, and Salesforce preferred; advanced Excel skills, project management tools, Visio, and working knowledge of SQL and emerging AI tools preferred. Ability to collaborate effectively across multiple departments and disciplines and work comfortably with all levels of the organization. Strong project management skills with demonstrated ability to manage competing priorities, meet deadlines, and drive process improvement. Exceptional written and verbal communication skills, with the ability to interact effectively with senior leadership, agency partners, and cross-functional teams. Bachelor's degree in business or related field preferred

SALARY RANGE

The pay range for this position is $85,000 to $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.​

PERKS & BENEFITS 4

weeks accrued paid time off, 8 paid national holidays per year, and 2 floating holidays Low cost and excellent coverage health insurance options that start on Day 1 (medical, dental, vision) Annual 401(k) Employer Contribution Free onsite gym and health center at our Woodbridge Location Resources to promote Professional Development (LinkedIn Learning and licensure assistance) Robust health and wellness program and fitness reimbursements Various Paid Family leave options including Paid Parental Leave Tuition Reimbursement

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".#LI-DNI