Learning and Development Supervisor

Job DescriptionWe 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 needsManage program timelines, communications, logistics, and stakeholder engagementEnsure 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 leadersFacilitate sessions on core topics such as coaching, communication, performance management, and team leadershipFoster interactive, learner-centered environments that drive reflection, skill development, and real-world applicationAdapt delivery style to meet diverse audiences and leadership levelsDesign and maintain leadership content, facilitator guides, and participant materialsApply adult learning principles to create engaging, practical learning experiencesContinuously iterate content based on feedback, data, and evolving business needsPartner with HR and business leaders to identify leadership gaps and development prioritiesBuild strong relationships and serve as a trusted advisor on leadership developmentSupport leadership initiatives and broader talent strategiesRequirements 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.Educations/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 development3+ years facilitating leadership training for people leadersExperience owning and managing programs from design through delivery and evaluationStrong facilitation, communication, and stakeholder management skills5+ 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 yearRobust wellness & health and fitness reimbursement programs401(k) bonus programTuition reimbursementAuto and home insurance discountsVolunteer opportunities2:1 donation matching programCompany-paid life and disability insurance plansOptional medical, dental, vision, legal, pet insurance, FSA and identity theft protection plansSalary 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”.Job DetailsJob Type: Regular Full-TimeCategory: ClaimsSalaried: Salaried