Senior Learning and Development Specialist

 

Senior Learning and Development Specialist

 

Overview
We’re seeking an experienced and highly skilled Senior Learning and Development Specialist to deliver comprehensive training programs that enhance the skills, knowledge, and performance of our Independent Agent Channel claims department. Additionally, you will assist with the design and development of engaging training materials, including e-learning modules, workshops, and instructional guides. This role is essential to driving organizational performance through strategic learning initiatives that align with business priorities and elevate claims handling excellence.

 

Key Responsibilities

• Facilitate, engaging training sessions tailored for adult learners at all levels, including senior-level staff and tenured professionals.
• Develop the end-to-end design, and deployment of training programs, including classroom instruction, virtual delivery, e-learning, and performance support tools.
• Partner with business leaders to conduct needs assessments, identify skill gaps, and align learning solutions with strategic goals.
• Serve as a trusted coach and mentor to less experienced L&D team members, enhancing technical proficiency and professional development.

• Stay ahead of industry trends, regulatory updates, and instructional design innovations to ensure learning strategies remain cutting-edge.

• Champion the use of technology and innovation in training, including authoring tools, virtual platforms, and performance analytics.
• Assist with initiatives to embed continuous learning into the claims culture, including knowledge sharing, refresher programs, and learning communities.

• Hold regular feedback meetings and sharing of expectations and results between employees and managers.

 

Qualifications

• Bachelor’s degree required; advanced degree or industry certifications (e.g., CPLP, ATD, AIC, or similar) strongly preferred.
• Minimum 5 years of experience in learning and development
• Experience in property & casualty claims handling or insurance preferred.
• Excellent presentation and facilitation skills.
• Understanding of concepts used in; instructional design, adult learning theory, and facilitation of both technical and behavioral training.
• Advanced proficiency in instructional tools such as Camtasia, Adobe Creative Cloud, SnagIT, LMS Platforms, Articulate Storyline, or similar.
• Strong analytical skills with the ability to assess performance data, identify trends, and drive continuous improvement.
• Exceptional communication, presentation, and stakeholder engagement skills.
• Demonstrated ability to lead projects, manage competing priorities, and influence without authority across cross-functional teams.
• Deep understanding of claims systems, workflows, compliance requirements, and customer service excellence in an insurance context.

 

 

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”.