Learning and Development Supervisor

Plymouth Rock Assurance • Boston, MA

3d • $114,000 - $147,000 • Hybrid

About The Position

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.

Requirements

• 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.

Nice To Haves

• Knowledge of insurance policies and an understanding of P&C insurance industry preferred.

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

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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level