Learning and Development Supervisor

About the role

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 Rock’s 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

• 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.

Qualifications

• 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.

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.

Pay

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.