Job Description  

Are you ready to join a dynamic team in the world of auto claims learning and development? We are seeking a dedicated and enthusiastic Learning and Development Training Specialist to join our team. The ideal candidate will be responsible for delivering and at times designing, and developing comprehensive training programs that enhance the skills, knowledge, and performance of our Independent Agent Channel claims department. This role will play a crucial part in driving the company’s growth by ensuring that our team is well-equipped to meet business goals. 

Responsibilities

• Facilitate training sessions, both in-person and virtually, ensuring effective delivery and engagement.
• Support the onboarding process by providing new hire orientation and training.
• Assist with Design, develop, and implement engaging training materials, including e-learning modules, workshops, and instructional guides.
• Evaluate the effectiveness of training programs through assessments, feedback, and performance metrics.
• Collaborate with department managers to identify training needs and develop tailored learning solutions.
• Coordinate regular feedback meetings and share expectations and results between employees and managers.
• Fluency with learning management system (LMS) to ensure all training records are accurately maintained.
• Maintain up-to-date knowledge of industry trends and best practices in learning and development.
• Provide coaching and support to employees to enhance their professional growth.

Qualifications

• Excellent presentation and facilitation skills.
• Prior experience facilitating highly effective claims technical and system training.
• Experience in a claims handling role or advanced knowledge of claim departmental processes, procedures and responsibilities gained through exposure in a similar role with a Property & Casualty insurance carrier.
• Proficiency in e-learning authoring tools and LMS platforms.
• Strong interpersonal, problem-solving, and organizational skills.
• Demonstrated ability to manage multiple projects simultaneously, prioritize competing deadlines, and execute tasks efficiently.
• Exceptional written and verbal communication skills.
• Ability, aptitude, and desire to develop and train employees at all levels within the organization.
• Champions a customer‑first approach by exceeding expectations through every interaction.
• Bachelor’s degree (B.A.) from a four-year college or university, or a combination of education and experience.
• Strong knowledge of instructional design principles and adult learning theories.
• Experience with Instructional Design products such as Articulate RISE and Storyline, Camtasia, Adobe Creative, Cloud Bigtincan and SnagIT. 
• Travel between Claim offices as needed, potentially up to 25% of time.
• Certification in training delivery or instructional design (e.g., CPLP, ATD, or similar) is a plus.

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 

The pay range for this position is $65,000- $90,000 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity.

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”.

Location(s) 

695 Atlantic Avenue, Boston, Massachusetts 02111, United States