Senior Agency Operations Representative at Plymouth Rock

Step into a high-impact role where your work directly contributes to the success and efficiency of our Home Group at Plymouth Rock Assurance. Based in our Boston office, the Senior Agency Operations Representative plays a critical part in supporting and optimizing the experience of our expansive network of independent and direct agents. These partners represent a range of personal and commercial insurance products, including Auto, Home, Umbrella, and Commercial Auto.

In this dynamic position, you'll drive process enhancements, streamline agency onboarding, and help ensure a smooth, high-quality operational experience. If you're a detail-oriented, analytical thinker with a passion for learning, collaboration, and continuous improvement, this is your opportunity to grow your career and make a measurable difference.

Key Responsibilities

Agency Onboarding & Relationship Management

• Lead the onboarding process for new agencies and producers by handling appointments, building accurate profiles, and ensuring all setup details are completed seamlessly.
• Maintain and enhance existing agency relationships through timely updates to licensing, contracts, and system access.
• Proactively troubleshoot and resolve login or access issues, and support agents through changes or transitions.

Commission Management

• Configure, test, and maintain commission structures in internal systems with accuracy and timeliness.
• Investigate and correct commission discrepancies, work with Accounting on adjustments, and respond to agent and internal inquiries regarding payouts.

Process Improvement & Quality Assurance

• Collaborate with IT, Marketing, and Underwriting to test new features, identify bugs, and recommend system improvements using QA access.
• Help design and implement smarter workflows that reduce manual work and boost operational efficiency.

Resource Development & Team Enablement

• Develop and maintain clear, user-friendly documentation and quick-reference guides for agents, reps, and internal stakeholders.
• Assist in onboarding new team members by providing hands-on training, sharing best practices, and fostering a collaborative, supportive team environment.

Cross-Functional Support & Problem Solving

• Serve as a reliable point of contact for internal teams and external partners, identifying root causes and resolving issues promptly—or connecting people with the right resources when needed.

Qualifications

• Education: Bachelor’s degree (preferred); open to a variety of fields (e.g., Philosophy).
• Experience: Insurance industry experience a plus.
• Technical Skills: Proficiency in Microsoft Office Suite, especially Excel (data manipulation, formulas, basic reporting).
• Soft Skills:
• Exceptional attention to detail with a strong problem-solving mindset.
• Effective communicator—clear, concise, and comfortable collaborating with various teams and personalities.
• Highly organized and able to prioritize multiple projects in a fast-paced environment.
• A self-starter with the flexibility to work both independently and as part of a cross-functional team.

Perks and 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”.