Agency Trainer Jobs (NOW HIRING)

The Agency Trainer serves as a strategic partner and trusted resource for our independent agency partners with a primary focus on delivering training that drives production. This role combines expert training delivery, agency coaching, sales enablement, and relationship management to equip agents with the knowledge, skills, and tools needed to grow their businesses, improve quote and bind activity, enhance sales performance, and strengthen adoption of Plymouth Rock's products, services, technology capabilities, and sales processes. This individual must bring strong communication and presentation skills, a highly professional presence, and the ability to represent Plymouth Rock with credibility in both virtual and in-person settings. The Agency Trainer leverages Plymouth Rock resources, including the Sales Development Program trainings, to reinforce proven sales behaviors and support long-term agency growth.

Remote/Field-Based (Travel Required), New England Based Role, majority of travel in Massachusetts.

Responsibilities

Training & Development

• Develop and deliver engaging, interactive training sessions, both virtual and in-person, on Plymouth Rock's products, services, technology platforms, sales techniques.
• Customize training programs aligned with agency performance goals, market dynamics, and company objectives, with a clear focus on improving production outcomes.
• Provide one-on-one, small group, and large group training sessions Equip agents with best practices in sales techniques, prospecting strategies, and customer relationship management that help drive production growth and improve overall agency performance.

Agency Performance Support

• Understand agency profile and performance to assess strengths and identify gaps for coaching opportunities.
• Collaborate with field marketing leadership to support business growth strategies.
• Measure agency performance before and after training to evaluate impact, identify production lift, and adjust coaching strategies based on results.

• Use agency data, production trends, and training feedback to recommend targeted follow-up actions that help agencies convert training into measurable business growth.

Relationship Management

• Cultivate and maintain trusted, consultative relationships with independent agency partners across all lines of business and geographic regions.
• Communicate agency performance trends, learning opportunities, and emerging market insights to internal stakeholders, including field marketing and communications teams.

Market Expertise & Collaboration

• Partner with internal teams to align training content with broader business initiatives and field strategies.

• Maintain an active understanding of industry regulations, trends, and competitive landscape.

Qualifications

• 5+ years of experience in the insurance industry, preferably as an agent, underwriter, , or agency trainer.

• Demonstrated success in sales, customer relationship management, and/or business development, with experience connecting training activity to measurable performance or production results.
• Property & Casualty license is strongly preferred (or willingness to obtain within the first year of employment)
• Exceptional communication, presentation, and interpersonal skills.
• Ability to influence and motivate agency partners at all experience levels.
• Strong organizational skills with the ability to manage multiple priorities and deliver results.
• Comfort with frequent travel and delivering training both virtually and on-site.
• Prior knowledge of a learning management system preferred
• Ability to create strong, engaging, and informative training materials and presentation.

Salary Range

The pay range for this position is $68,000 to $97,000 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
• 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".