Mutual Opportunities
Head of Enrollment Technology Strategy & Delivery
Springfield, Massachusetts; Boston, Massachusetts
Thank you to our employees for voting us one of the top places to work in Massachusetts for five consecutive years!
Overview
A career with us means you’ll work alongside exceptional people and be empowered to reach your professional and personal goals. Our employees are at the foundation of what enables MassMutual to deliver on our purpose to help people secure their futures and protect the ones they love.
We embrace the idea that we all are stronger and better through our support for one another. We strive to create a culture where employees feel valued and are celebrated for who they are.
“Since our founding in 1851, mutuality has put our policyowners at the center of everything we do. At our core, we’re a company of people helping people in their time of need, and that spirit extends to the culture we’ve built at our company. Our employees support and rely on each other each day, collaborating to deliver the best solutions for our customers and help millions more secure their future and protect the ones they love.”
Job Description
MassMutual Worksite has an exciting opportunity for a proven leader who will focus on development and implementation of our long-term approach to enable a more efficient and effective enrollment technology eco-system. Partner with senior leaders in the business, distribution partners, enrollment technology firms to ensure alignment on strategy, technology and customer experience across all channels. You will act as enrollment technology champion and knowledge expert internally, while aligning with distribution to ensure our key account firms and distribution partners’ needs are understood and part of our internal strategy and delivery plan.
The Worksite Insurance business is growing as we aim to reach middle class workers in support of the company’s vision to provide financial well-being to all Americans. Worksite has achieved success in recent years distributing our Group Voluntary and Executive products through our multi-channel distribution relationships. In addition to your team members, you will work closely with members of the Enrollment Platform Solutions, New Business Implementation and Account Management teams.
The Impact
As the Head of of Enrollment Technology Strategy and Delivery, your responsibilities will include but are not limited to the following:
Accountable to develop the Enrollment Technology strategy of the future to support the ongoing growth and expansion of our Voluntary Worksite Benefits business while making it easier for our distribution partners and customers to work with us.
Provide Strategic insight and direction for enrollment technology and associated ben-tech solutions
Serve as the key resource on all-things enrollment technology and related processes.
Act as an enrollment solutions thought partner with distribution, service and operations.
Partner with enterprise technology teams on development of technology integrations between ben tech solutions and policy administration systems.
Align with distribution on strategic enrollment platforms and ben tech options to maximize distribution opportunities
Engage with customers to gain feedback on active development and roadmap input
Understand customer utilization to deliver metrics and analytics for continuous improvement opportunities across enrollment platforms and our value chain
Measure customer satisfaction including gathering feedback and sharing with internal partners
Other duties as assigned
The Minimum Qualifications
Bachelor’s degree or equivalent work experience
10+ years experience with enrollment platform technology and processes, product integrations, file formats, audit and test file feeds
5+ years of Voluntary benefits leadership experience as part of high performing teams
Demonstrated ability to lead and drive change & culture while bringing organization along the journey
Ability to focus on strategic goals and development without losing sight of day-to-day needs and complexities.
Excellent communication and interpersonal skills, both written and oral, to succeed in a fast-paced, team environment.
Successfully influence and navigate a matrixed organization; Be the arbiter of different points of view to reach decisions on requirements and delivery approach and timelines
8+ years experience with enrollment platform technology and processes, product integrations, file formats, audit and test file feeds
The Ideal Qualifications
Demonstrated ability to work cross-functionally to reconcile competing priorities while meeting organizational objectives
Advanced written and verbal communications skills
#LI-DNI
MassMutual is an equal employment opportunity employer. We welcome all persons to apply.If you need an accommodation to complete the application process, please contact us and share the specifics of the assistance you need.
MassMutual will accept applications on an ongoing basis until such time as a candidate has been offered employment. The job description includes the main duties of this position, which may evolve over time. You may be required to perform other duties not listed.
It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment.
Salary Range: $172,000-$225,700
Hiring Process
Explore
Explore our open jobs by clicking 'search jobs' to find a position that aligns with your experience and skills. You may also consider joining our Talent Network.
Apply
Click the “apply” button on that job posting to complete and submit your application. Your application will be reviewed by a recruiter, which, due to the volume of applications received, may take some time as we carefully consider each application.
Screen
After your application has been reviewed, if you meet the qualifications for the role, a recruiter will reach out to you to start a conversation.
Interview
If you are invited for an interview, you will be scheduled to meet with the hiring manager and hiring team.
Offer
If you are extended an offer to join MassMutual and accept, your start will be contingent upon a satisfactory background check.
Hire
If you accept the offer, we will be so excited to welcome you to the MassMutual community!
If you need an accommodation to complete the application process, please contact us and share the specifics of the assistance you need.
By the numbers*
- 85% of employee respondents say they are proud to work at MassMutual
-
90
% of employee respondents say the work they do at MassMutual is meaningful - 85% of employee respondents say they feel encouraged to come up with new and better ways of doing things
*Source: 2025 MassMutual employee engagement survey
Award-Winning Culture
MassMutual is guided by a single purpose: We help people secure their future and protect the ones they love. As a company operated for the benefit of our members and participating policyowners, we are defined by mutuality and our vision to provide financial well-being for all Americans. It’s more than our company structure — it’s our way of life. We are a company of people protecting people. Our company exists because people are willing to share risk and resources and rely on each other when it counts.
We strive to build a thriving community where everyone is valued, included, and feels that they belong.
At MassMutual, we Live Mutual.
How We Work
MassMutual’s flexible workplace approach combines the importance of connecting in person and the flexibility of working remotely. Our hybrid model puts collaboration first with employees coming in at least three days per week to our spectacular campus settings and also enjoying the flexibility of remote Fridays, company-wide remote weeks, and a bank of flexible remote weeks to use throughout the year.
Benefits for the whole you (and your loved ones)
There’s more to your life than your job and there’s more to your aspirations than a paycheck. We take a holistic view of compensation and benefits that provides the flexibility to create a healthy balance in your life for work, family, and community. We offer the benefits you’d expect, like medical, dental, 401(k), and generous vacation time, but we also offer ones you might not expect, like three paid days for volunteering, a $1,250 annual Well-Being Wallet, and up to 320 hours of caregiver leave.
Explore some of our offerings below. Benefit details can be found here.
Why MassMutual?
Kevin
Compliance Consultant
Seth
Service Management Consultant
Kymberly
Head of Experience Journey Mapping
where we work
Springfield Office
1295 State Street, Springfield, MA
Boston Office
10 Fan Pier Blvd, Boston, MA
New York Office
2 Park Ave,
New York, NY
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