Learning and Development Supervisor

Plymouth Rock Assurance; Boston (MA); On-site; USD 114,000 - 147,000; Full time

Benefits offered by this job

4 weeks accrued paid time off + 9 paid

National holidays

401(k) bonus

Tuition reimbursement

Auto and home insurance discounts

Volunteer opportunities

2:1 donation matching

Company-paid life and disability

Various insurance plans

Job summary

Plymouth Rock Assurance in Boston, MA seeks a Learning and Development Supervisor to design, deliver, and manage leadership development programs across its Independent Agent organization. The role blends expert facilitation with end-to-end program ownership, ensuring scalable, practical leadership experiences aligned to business priorities.

The ideal candidate has strong executive presence, strategic thinking, and proven experience developing leaders at multiple levels.

Qualifications

• Design and facilitate highly effective leadership training.
• Experience designing and delivering programs from inception through evaluation.
• Strong facilitation, communication, and stakeholder management is essential.
• 5+ years in learning & development, leadership development, or talent development.
• 3+ years facilitating leadership training for people leaders.
• Knowledge of P&C insurance industry is a plus.

Responsibilities

• Own full lifecycle of leadership development programs from design to execution and improvement.
• Align program strategy with business priorities and HR/leadership needs.
• Manage timelines, communications, logistics, and stakeholder engagement.
• Deliver leadership programs in-person, virtual, and hybrid formats.
• Facilitate sessions on coaching, communication, performance management, and team leadership.
• Iterate content based on feedback,data, and evolving business needs.
• Partner with HR and business leaders to identify leadership gaps and development priorities.

Skills

Leadership development

Facilitation

Stakeholder management

Communication

Travel readiness

Education

BA/BS in HR, Organizational Development, Education, Business

Job description

Learning and Development Supervisor

Boston, Massachusetts, United States

We are seeking a dynamic and experienced Leadership Development Facilitator & Program Owner to design, deliver, and manage high-impact leadership development programs across our Independent Agent organization. This role blends expert facilitation with end-to-end program ownership, ensuring leadership experiences are practical, scalable, and aligned to business priorities. The ideal candidate is a skilled facilitator with strong executive presence, a strategic mindset, and proven experience developing leaders at multiple levels.

Responsibilities

• Own the full lifecycle of leadership development programs for Plymouth Rocks Independent Agent organization, from design through execution and continuous improvement.
• Align program strategy with business priorities, human resources and leadership capability needs.
• Manage program timelines, communications, logistics, and stakeholder engagement.
• Ensure consistency, scalability, and quality across all program offerings and in alignment with the broader Human Resource content.
• Deliver engaging leadership development programs (in-person, virtual, hybrid) for emerging, frontline, and mid-level leaders.
• Facilitate sessions on core topics such as coaching, communication, performance management, and team leadership.
• Foster interactive, learner-centered environments that drive reflection, skill development, and real-world application.
• Adapt delivery style to meet diverse audiences and leadership levels.
• Design and maintain leadership content, facilitator guides, and participant materials.
• Apply adult learning principles to create engaging, practical learning experiences.
• Continuously iterate content based on feedback, data, and evolving business needs.
• Partner with HR and business leaders to identify leadership gaps and development priorities.
• Build strong relationships and serve as a trusted advisor on leadership development.
• Support leadership initiatives and broader talent strategies.

Requirements and Qualifications

• Ability to design and facilitate highly effective leadership training.
• Proven ability to effectively organize, prioritize, and manage deliverables to meet organizational objectives.
• Ability to understand and utilize company resources effectively and build positive relationships within all areas and intercompany partners.
• Demonstrated capability and commitment to developing, coaching, and upskilling employees across all organizational levels.
• Commitment to excellence in the delivery of True Service.
• Exceptional interpersonal, analytical, and problem-solving capabilities, complemented by strong written and verbal communication skills.
• Willingness and flexibility to travel between claims offices as needed, with up to 25% travel required to support business objectives.
• Knowledge of insurance policies and an understanding of P&C insurance industry preferred.

Education / Experience

• A minimum of a BA/BS degree (HR, Organizational Development, Education, Business, or related field preferred; Advanced degree a plus).
• 5+ years of experience in learning & development, leadership development, or talent development.
• 3+ years facilitating leadership training for people leaders.
• Experience owning and managing programs from design through delivery and evaluation.
• Strong facilitation, communication, and stakeholder management skills.
• 5+ years of experience in a claims processing role or advanced knowledge of departmental processes, procedures and responsibilities gained through exposure in a similar role with a Property & Casualty insurance carrier preferred.

Perks and Benefits

• 4 weeks accrued paid time off + 9 paid national holidays per year.
• Robust wellness & health and fitness reimbursement programs.
• 401(k) bonus program.
• Tuition reimbursement.
• Auto and home insurance discounts.
• Volunteer opportunities.
• 2:1 donation matching program.
• Company-paid life and disability insurance plans.
• Optional medical, dental, vision, legal, pet insurance, FSA and identity theft protection plans.

Salary Range: The pay range for this position is $114,000 to $147,000 annually. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity.

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