Job Description

The Agency Trainer & Development Supervisor ensures independent agency partners receive the product, system, and sales training needed to grow their business with Plymouth Rock Assurance, while driving book consolidation results and managing service center agency relationships.

The Supervisor will oversee agency development initiatives, lead employee development, identify growth opportunities, and collaborate across the organization to deliver solutions that improve agency performance and strengthen business partnerships.

Responsibilities:

Team Leadership & Development

• Provide leadership, coaching, and performance management for the Agency Services Representative and Agency Trainers.
• Prioritize and balance team workload across new agent training, refresher training, book consolidation outreach, and Service Center relationship management
• Foster a collaborative, accountable team culture aligned with the company's culture statement and Best Place to Work objectives
• Support onboarding and ongoing skill development for the team, including product knowledge, systems, and presentation/training delivery skills

Agency Training Oversight

• Oversee the development and quality of training materials across Personal Auto, Homeowner, Personal Umbrella, and Commercial Auto, ensuring materials are reviewed quarterly for accuracy
• Ensure trainers support all new product, system, and enhancement launches (e.g., Easy Quote expansion, Auto Cross Sell from Home) with training delivered on schedule
• Partner across Marketing Department to identify and prioritize strategic training opportunities across the footprint

Sales Development Program Leadership

• Oversee the strategic direction, execution, and growth of the Sales Development Program
• Develop and implement initiatives that support agency profitability, production growth, and sales effectiveness
• Partner with agency leadership to identify opportunities and deliver customized development plans
• Facilitate training, coaching, and consultative support to participating agencies
• Measure program effectiveness and communicate results to leadership

Book Consolidation & Service Center Oversight

• Oversee the consolidation efforts to drive agents toward issuing book roll (remarketing) policies, ensuring consistent outreach cadence and follow-through on commitments
• Monitor and report Service Center relationship health across the assigned agency book
• Ensure timely identification, escalation, and resolution of agency-reported issues related to consolidation or Service Center, with clear communication back to the agent

Reporting & Continuous Improvement

• Track and report team performance against training completion timelines, agent adoption targets, and consolidation/Service Center metrics
• Measure and report Sales Development Program effectiveness and results to leadership on a regular cadence
• Identify trends in agent feedback and training/consolidation outcomes; recommend process or content improvements

Stakeholder Collaboration

• Represent the voice of the independent agency in internal forums, facilitating a continuous feedback loop between agents and the business
• Attend marketing meetings and stay current on state-level initiatives, products, and system changes affecting the team's work

Qualifications:

• 5+ years of experience in agency training or agency relationship management within an insurance or independent agency (IA) distribution environment
• Experience leading or contributing to a sales, growth, or agency development program, with the ability to build customized plans and consultative relationships with agency leadership
• Prior people leadership or supervisory experience preferred; demonstrated ability to coach, develop, and hold a team accountable to service and performance standards
• Strong presentation and training delivery skills, with experience designing and delivering both in-person and virtual training
• Working knowledge of Personal Lines products (Personal Auto, Homeowner, Personal Umbrella) and book roll/remarketing processes
• Comfortable managing competing priorities across training delivery, consolidation outreach, and relationship management
• Strong organizational, written, and verbal communication skills; ability to translate agent feedback into clear, actionable recommendations
• Ability for weekly travel for in-person agency training and relationship visits (coverage across NJ, PA, NY, CT, NH, MA)
• Bachelor's degree preferred; P&C license required or must be obtained within an agreed timeframe of hire

Salary Range

The pay range for this position is $95,000 to $133,500 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
• 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”.