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Underwriting Facilitator, Digital Learning - 100% REMOTE at MassMutual

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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.

Offers of employment are contingent on the completion of satisfactory references, background investigation, and (if applicable) any federal securities law requirements/FINRA regulations (including fingerprinting) and/or passing of a drug screening.

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.

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What are MassMutual Perks + Benefits

MassMutual Benefits Overview

At MassMutual, employees have the opportunity to earn a competitive salary and bonus, enroll in an
array of benefits, and participate in programs and services that support healthy lifestyles, assist them
in building financial security for themselves and their families and help them live well-balanced lives.

Volunteer in local community
Every action supporting a common cause is meaningful, and our employees make a difference in their own communities through our Matching Gift, Matching Time and Volunteer Time Off Programs.
Partners with Nonprofits
Every year, MassMutual and the MassMutual Foundation invest more than $20 million focused on advancing economic opportunity.
Eat lunch together
Intracompany committees
Daily sync
Team owned deliverables
Team based strategic planning
Open office floor plan
Documented equal pay policy
Dedicated Diversity/Inclusion Staff
Highly diverse management team
More than half of our Board of Directors are comprised of women and people of color, making it one of the most diverse groups in the industry.
Unconscious bias training
Diversity manifesto
Diversity Employee Resource Groups
Hiring Practices that Promote Diversity
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
A health care flexible spending account (FSA) allows employees to save money on a before-tax basis for eligible medical, dental and vision expenses, subject to IRS limits.
Disability Insurance
For details on short term and long term disability insurance please visit
Dental Benefits
Basic Dental covers preventive and basic restorative care; Major Dental covers all that Basic covers, plus restorations and orthodontia (limits apply).
Vision Benefits
Health Insurance Benefits
To learn more about our Health and Welfare Benefits please visit:
Life Insurance
For more information about our Life Insurance Benefits please visit:
Wellness Programs
Onsite Gym
Mental Health Benefits
Retirement & Stock Options Benefits
In addition to our 401(k), MassMutual a cash balance plan that provides an account-based pension benefit based on accruals of pay credits and interest credits.
401(K) Matching
Performance Bonus
Match charitable contributions
Every action supporting a common cause is meaningful, and our employees make a difference in their own communities through our Matching Gift and Matching Time Programs.
Child Care & Parental Leave Benefits
Child Care Benefits
Dependent care flexible spending account to allow you to set aside before tax dollars to pay for certain eligible child care expenses.
Generous Parental Leave
Leave for birth mothers of 18 weeks of fully paid leave. Non-birth mothers, fathers and adoptive parents eight weeks of fully paid parental leave.
Flexible Work Schedule
Flexible work arrangements, including telecommuting, are available in many departments across the company.
Family Medical Leave
Caregiver leave: Up to two weeks paid leave to care for a loved one. Bereavement Leave: 15 days of paid time off to grieve the loss of a loved one with the employee defining who the loved one is.
Adoption Assistance
Vacation & Time Off Benefits
Generous PTO
Paid Volunteer Time
Three days of paid time off is available to employees annually to give back to their communities, by sharing their time and talent with a cause close to their heart.
Paid Holidays
Paid Sick Days
Occasional illness: up to 5 days per calendar year.
Perks & Discounts
Casual Dress
Commuter Benefits
Game Room
Fitness Subsidies
Professional Development Benefits
Job Training & Conferences
Tuition Reimbursement
Lunch and learns
Cross functional training encouraged
Promote from within
Online course subscriptions available
Customized development tracks
Paid industry certifications

Additional Perks + Benefits

To learn more about our comprehensive benefits please visit:

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