Sales Operations (Remarketing) Supervisor

Plymouth Rock Assurance•Boston, MA

12h•Onsite

About The Position

The Sales Operations Supervisor leads a results-driven team responsible for executing Plymouth Rock's remarketing program and providing accurate, timely quoting support to the Independent Agent channel. In this role, you will manage daily operations, coach and develop team members, and partner with Marketing to drive program performance and agency relationships, while contributing to initiatives that support the broader customer service organization.

Requirements

3+ years of experience in operations or a related field, with a working knowledge of the Independent Agent channel preferred, prior leadership experience a plus.
Understanding of personal lines insurance products and the quoting process preferred; commitment to developing deep product and program knowledge expected.
Strong technical aptitude and ability to learn new systems quickly; knowledge of database management, XML file structure and policy systems, preferred along with advanced Excel skills including tables, data sorting, and formulas.
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.

Nice To Haves

prior leadership experience a plus
working knowledge of the Independent Agent channel preferred
Understanding of personal lines insurance products and the quoting process preferred
knowledge of database management, XML file structure and policy systems, preferred

Responsibilities

Partner with Marketing and Product to support new agency onboarding, including system setup coordination and participation in agency kickoff meetings.
Oversee the full remarketing quote life cycle — including monthly data pulls, quote submission and bot monitoring, Quality Assurance (QA) of results, and final delivery to agencies — ensuring quote accuracy and consistent adherence to established deadlines and providing hands-on quoting support to the team as needed.
Monitor and manage quote forecasts and volumes, workload distribution, and team staffing to ensure appropriate coverage and consistent service levels, prioritizing high-value agency requests based on business importance and proactively addressing capacity needs and bottlenecks.
Manage the Sales Operations QA program, including individual QA results for team members, monitoring, and corrective action to maintain a team accuracy standard of 95% or better.
Oversee the execution of sales-related project work on behalf of customer service and underwriting, ensuring accuracy, compliance, adherence to deadlines, and consistent compliance with established quality standards.
Lead and contribute to strategic projects and initiatives that grow the remarketing program and increase operational efficiency, including implementing new guidelines and updates from Marketing and Product, driving process improvements, pursuing automation opportunities, and partnering with the Product team on ongoing bot refinement.
Develop, maintain, and update Standard Operating Procedures and Carrier Mapping reporting to ensure workflow consistency, accuracy, and alignment across the team.
Administer and optimize work management tools, including Agency Zoom and Salesforce, ensuring the team is utilizing available resources effectively and in alignment with operational priorities.
Address and escalate any issues or friction points that delay meeting operational standards. Address agency disengagement before it impacts conversation rates.
Own monthly team metrics, executive reporting, and quarterly marketing reviews, compiling and presenting team performance data and service metrics to leadership and stakeholders, and maintaining accountability to Marketing for consistent service delivery and performance reporting.
Coach, develop, and motivate team members through regular 1:1s, performance feedback, and individualized development plans that build expertise and support career growth.

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