Top 105 Learning and development facilitator Jobs in Boston, Ma

Learning and Development Supervisor
Plymouth Rock Assurance Corporation —Boston, MA
- $114,000 - $147,000 a year
- 5 years
- Bachelor of Science
- Office
- Paid holidays
- Disability insurance
Quick Apply
LEARNING FACILITATOR, Office of the Provost
Boston University —Boston, MA
- Weekends as needed
- Remote
- Computer science
- Azure
- Computer Science
Learning & Development Manager
ClearView Healthcare Partners —Boston, MA
- $130,000 a year
- Office
- Continuous improvement
- Senior level
Manager, Staff Development and DEI
Museum of Fine Arts —Boston, MA
- $110,000 - $115,000 a year
- Full-time
- 7 years
- Education
- Psychology
Overture STEAM Teacher (Greater Boston Area)
Overture Games —Boston, MA
- From $70 an hour
- Part-time
- School experience
- Classroom
- Mentoring
- Employee discount
- Professional development assistance
Quick Apply
Sales Development Representative (Immediate Start)
memoryBlue —Waltham, MA
- Urgently hiring
- Research
- Mid-level
- Office
- Health insurance
- Dental insurance
Kids’ Cooking & Nutrition Instructor (After‑School, Part‑Time)
Kids' Test Kitchen —Boston, MA
- $60 - $120 a day
- Choose your own hours
- Background check
- Driver's License
- Experience working with children
- Flexible schedule
Quick Apply
12d
Behavior Technician Trainer
Intercare Therapy —Boston, MA
- $27 - $28 an hour
- Full-time
- School experience
- Mid-level
- Driver's License
Quick Apply
Learning and Development Specialist
Jeanne D Arc Credit Union —Lowell, MA
- $64,063 - $96,094 a year
- Full-time
- 5 years
- Mid-level
- Office
Quick Apply
Instructional Designer
Agero —Medford, MA
- $69,000 - $94,000 a year
- Remote
- Data analysis skills
- Mid-level
- Analysis skills
- Paid holidays
- Disability insurance
Quick Apply
Volunteer Advisor
Oxfam America —Boston, MA
- $75,000 - $80,000 a year
- Full-time
- Remote
- Bilingual
- Writing skills
- Mid-level
Quick Apply
AI Learning Specialist
Analysis Group, Inc. —Boston, MA
- $85,000 - $100,000 a year
- Hybrid work
- Writing skills
- Mid-level
- Bachelor's degree
1d
Learning & Development Manager, AI Enablement
Analysis Group, Inc. —Boston, MA
- $130,000 - $150,000 a year
- Hybrid work
- Writing skills
- 8 years
- Bachelor's degree
Learning Designer
Harvard Graduate School of Education —Cambridge, MA
- $76,000 - $81,000 a year
- Full-time
- Hybrid work
- Writing skills
- Master's degree
- 1 year
- Commuter assistance
- Health insurance
Quick Apply
Sr. Manager, Commercial Training
Agios Pharmaceuticals —Cambridge, MA
- $131,035 - $196,553 a year
- Remote
- 3 years
- Bachelor's degree
- Travel
- Health insurance
Speech@Emerson Course Facilitator - CD645 | Language and Literacy Disabilities
Emerson College —Boston, MA
- Part-time
- Remote
- Computer literacy
- Writing skills
- Clinic experience
Associate Director of Youth Development
Just A Start —Cambridge, MA
- $80,000 - $90,000 a year
- Weekends as needed
- Hybrid work
- Google Workspace
- High school
- Office
- Paid holidays
- Disability insurance
Manager
Museum of Fine Arts —Boston, MA
- $110,000 - $115,000 a year
- Full-time
- 7 years
- Education
- Psychology
Community Connections Facilitator (SY26-27)
Boston Public Schools —Boston, MA
- Weekends as needed
- School experience
- Experience working with individuals with disabilities
- Computer literacy
AI Design Facilitator and Forward-Deployed Engineer II
Deloitte —Boston, MA
- $82,600 - $162,800 a year
- Full-time
- Up to 50% travel
- Bachelor's degree
- Product management
1d

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Learning and Development Supervisor

Plymouth Rock Assurance Corporation -
Boston, MA

Quick Apply

Job Details

$114,000 - $147,000 a year

Benefits

Paid holidays
Disability insurance
Health insurance
Dental insurance
Flexible spending account
Tuition reimbursement
Paid time off
Leadership training provided
Vision insurance
Gym membership
Pet insurance

Qualifications

Program design
Coaching
Leadership training instructional design
Leadership development
Team development
Instructor-led training (training delivery method)
Leadership training (staff training program)
Managing projects
Leadership development programs
Workshop facilitation experience
Project stakeholder communication
Stakeholder relationship building

Full Job Description

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.

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 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”.

Quick Apply

Refine Your Search

learning and development facilitator jobs in boston, ma

Learning and Development Supervisor

LEARNING FACILITATOR, Office of the Provost

Learning & Development Manager

Manager, Staff Development and DEI

Overture STEAM Teacher (Greater Boston Area)

Sales Development Representative (Immediate Start)

Kids’ Cooking & Nutrition Instructor (After‑School, Part‑Time)

Behavior Technician Trainer

Learning and Development Specialist

Instructional Designer

Volunteer Advisor

AI Learning Specialist

Learning & Development Manager, AI Enablement

Learning Designer

Sr. Manager, Commercial Training

Speech@Emerson Course Facilitator - CD645 | Language and Literacy Disabilities

Associate Director of Youth Development

Manager

Community Connections Facilitator (SY26-27)

AI Design Facilitator and Forward-Deployed Engineer II

I want to receive the latest job alert for learning and development facilitator in boston, ma

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