Leadership Development Architect

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

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.