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MassMutual Underwriting Facilitator, Digital Learning - 100% REMOTE in Springfield, Massachusetts

Digital Operations seeks a skilled facilitator for both synchronous and asynchronous, digital learning and training programs for underwriters . We seek a motivated and passionate individual to interact, engage and maintain effective learning and development courses through the use of gamification, educational tools, and other engaging learning solutions.

Our focus is to deliver and create the most informative, innovative, and imaginative learning solutions in our industry!

This is a remote position so candidates must be comfortable working from home and on a primarily remote team . Candidates must be self-motivated, disciplined, and also be comfortable working independently . Must be able to communicate and maintain working relationships via email, phone, live video calls, and chat.

Key Responsibilities and Percentage of Time

  • 50%+: Facilitating learning and training programs through hybrid or standard training for life underwriters by creatively engaging and interacting with adult learners of varying levels.

  • 25%+: Collaborating directly with peers, stakeholders, and subject matter experts to understand learning needs and objectives and consult on technology options and best practices; Supporting Projects and Content Development for different training needs in the Organization; researching and implementing new practices to always remain cutting edge in synchronous and asynchronous facilitation.

  • 25%: Life underwriting production

Minimum qualifications required:

  • 3+ years of experience with life underwriting, mentoring underwriters and or facilitating a variety of learning methodologies to underwriters, i.e. eLearning, virtual instructor-led, in-classroom courses, and other development material

  • Strong facilitation skills with the ability to engage and interact with adult learners of all levels

  • Basic design concept and ability to create training based on materials and/or ability to develop and design training material independently and as a team

  • Exceptional interpersonal, and communication skills

  • Manage time and priorities effectively

  • Display composure and patience while keeping spirits and energy levels up

  • Come to work willing to laugh and have fun!

Preferred qualifications:

  • Previous LMS and/or Canvas experience

  • Underwriting continuing education (Authority Limit Increases, ALUs, LOMAs, etc.)

  • Facilitation Certification (s) i.e. Certified Training Facilitator, Certified Master Facilitator, Virtual Facilitation Certification, Instructional Design Certification, etc.

  • Strong attention to detail, critical thinking, and analysis skills, including an understanding of industry measurement standards for learning

  • Ability to fully design and implement training for a variety of learners using industry-standard design and development concept



MassMutual is an Equal Employment Opportunity employer Minority/Female/Sexual Orientation/Gender Identity/Individual with Disability/Protected Veteran. We welcome all persons to apply. Note: Veterans are welcome to apply, regardless of their discharge status.

If you need an accommodation to complete the application process, please contact us ( and share the specifics of the assistance you need.

At MassMutual, we focus on ensuring fair, equitable pay by providing competitive salaries, along with incentive and bonus opportunities for all employees. Your total compensation package includes either a bonus target or in a sales-focused role a Variable Incentive Compensation component. For more information about our extensive benefits offerings please check out our Total Rewards at a Glance. (