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Plymouth Rock Assurance · 20 hours ago

Learning & Development Facilitator

Boston, MA

Full-time

Onsite

Mid Level

$60K/yr - $95K/yr

3+ years exp

Plymouth Rock Assurance is seeking an experienced Learning & Development Facilitator to join their Human Resources team in Boston. The role focuses on delivering engaging training programs that enhance the knowledge and skills of employees, with responsibilities including facilitating training sessions, adapting approaches to meet learner needs, and supporting the continuous improvement of training materials.

Auto InsuranceFinancial ServicesInsurance

Responsibilities

Facilitate engaging, instructor-led training sessions for adult learners across a variety of roles, experience levels, and learning styles

Adapt facilitation approaches in real time to meet learner needs, encourage participation, and reinforce practical application of concepts

Partner with HR and business leaders to prepare learners and stakeholders before training, reinforce expectations during sessions, and support post-training follow-through

Support the enhancement and continuous improvement of existing training materials, activities, and facilitator guides to ensure effective delivery

Utilize assessments, knowledge checks, and learner feedback to evaluate training effectiveness and identify opportunities for improvement

Stay current on facilitation best practices, adult learning trends, and delivery technologies to ensure training remains engaging and relevant

Contribute to initiatives that promote a culture of continuous learning, including refresher sessions, knowledge sharing, and learning communities

Qualification

Adult learning theoryInstructional designFacilitation skillsMicrosoft PowerPointLMS platformsVirtual meeting toolsStakeholder engagementCustomer service experienceMulti-priority managementCommunication skillsCollaboration skills

Required

Bachelor's degree or 3+ years of relevant training or facilitation experience; industry certifications (e.g., CPLP, ATD, AIC, or similar) preferred but not required

Minimum 3 years of experience facilitating learning and development programs for adult learners

Strong facilitation and presentation skills, with demonstrated ability to engage and influence diverse audiences

Working knowledge of adult learning theory and instructional design concepts as applied to training delivery

Proficiency with instructional and facilitation tools such as Microsoft PowerPoint, LMS platforms, virtual meeting tools, Articulate RISE, or similar

Ability to analyze training feedback and performance data to support continuous improvement

Excellent communication, collaboration, and stakeholder engagement skills

Proven ability to manage multiple priorities, lead training initiatives, and influence without direct authority across cross-functional teams

Travel up to 25% in the Northeast (MA, NH, CT, PA, NY, NJ) to deliver training programs

Preferred

Experience in customer service and/or insurance preferred; state P&C license or willingness to become licensed a plus

Benefits

Paid time off

Free onsite gym at our Boston location

Tuition reimbursement

Low cost and excellent health insurance coverage options that start on Day 1 (medical, dental, vision)

Robust health and wellness programs

Auto and home insurance discounts

Matching donation opportunities

Annual 401(k) employer contribution

Various Paid Family leave options including Paid Parental Leave

Resources to promote professional development

Convenient locations and pre-tax commuter benefits

Company

Plymouth Rock Assurance

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Founded in 2001

Boston, Massachusetts, USA

1001-5000 employees