Plymouth Rock Assurance
Training and Quality Analyst
🇺🇸 Remote - Boston, MA
🕑 Full-Time
💰 TBD
💻 Learning & Development
🗓️ July 16th, 2025
Edtech.com's Summary
- Develop and deliver interactive training sessions on insurance products, services, technology platforms, and sales techniques.
- Customize training programs based on agency performance goals and market needs.
- Assess agency performance, identify gaps, and provide coaching to improve results.
- Collaborate with field marketing leadership to implement business growth strategies.
- Maintain trusted relationships with independent agency partners across various lines of business.
- Empower agents with sales tactics, prospecting strategies, and product knowledge.
- Partner with internal teams to align training with business initiatives and stay updated on industry trends.
- Require 5+ years of insurance industry experience, preferably as an agent or trainer, with strong communication and organizational skills.
- Strong preference for candidates with Property & Casualty license and ability to travel frequently.
- Offer comprehensive benefits including paid time off, health insurance from day one, 401(k) matching, tuition reimbursement, and professional development resources.
Training and Quality Analyst Full Description
Location: Remote/Field-Based (Travel Required), New England Based Role, majority of travel in Massachusetts.
Position Summary
The Agency Trainer serves as a strategic partner and trusted resource for our independent agency partners, driving their success through targeted training and business development support. This role combines expert training delivery, agency coaching, and relationship management to equip agents with the knowledge, skills, and tools to grow their businesses, enhance sales performance, and build a robust understanding of Plymouth Rock’s, products, services and technology capabilities. The Agency Trainer is a pivotal role, blending technical expertise, sales acumen, and relationship management to support the long-term growth and success of our valued agency partners.
Key Responsibilities
Training & Development
- Develop and deliver engaging, interactive training sessions (virtual, in-person, small and large group) on Plymouth Rock’s products, services, technology platforms and sales techniques.
- Develop and customize training programs aligned with agency performance goals, market dynamics, and strategic sales objectives.
- Develop and provide one-on-one, small group, and large group training sessions tailored to agency needs that support marketing objectives.
Agency Performance Support
- Understand agency performance and assess strengths, identify gaps, and provide actionable coaching to agency partners.
- Collaborate with field marketing leadership to build and execute business growth strategies.
- Offer guidance to new and developing agents to help them establish a strong understanding of Plymouth Rocks products and underwriting appetite.
- Measure agency performance pre/post training.
Relationship Management
- Cultivate and maintain trusted, consultative relationships with independent agency partners across all lines of business and geographic regions.
- Serve as a primary point of contact for agency training needs and success initiatives.
- Communicate agency performance trends, learning opportunities, and emerging market insights to internal stakeholders, including field marketing and communications teams.
Sales Enablement & Product Education
- Empower agents with effective sales techniques, prospecting strategies, and customer relationship management best practices.
- Ensure agents possess deep product knowledge across all applicable lines of business.
- Promote the use of Plymouth Rock’s sales tools, marketing resources, and technology to drive agency success.
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.
- 5+ years of experience in the insurance industry, preferably as an agent, agency owner, or agency trainer.
- Demonstrated success in sales, customer relationship management, and/or business development.
- Property & Casualty license is strongly preferred
- 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.
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
695 Atlantic Avenue, Boston, Massachusetts 02111, United States
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