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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:
The Minimum Qualifications
The Ideal Qualifications
#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.
California residents: For detailed information about your rights under the California Consumer Privacy Act (CCPA), please visit our California Consumer Privacy Act Disclosures page.
Salary Range: $172,000-$225,700
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.
California residents: For detailed information about your rights under the California Consumer Privacy Act (CCPA), please visit our California Consumer Privacy Act Disclosures page.
Salary Range: $172,000-$225,700
MassMutual Boston, Massachusetts, USA Office





Our new Boston campus opened in November in the Seaport neighborhood.




Just like MassMutual, Boston's Seaport district is surrounded by decades of history, yet is now being recognized as a hub for digital innovation and professional growth. With us you can develop the skills you need to build a successful future and connect with talented and collaborative colleagues working together to help people secure their future and protect the ones they love.
What you need to know about the Boston Tech Scene
Boston is a powerhouse for technology innovation thanks to world-class research universities like MIT and Harvard and a robust pipeline of venture capital investment. Host to the first telephone call and one of the first general-purpose computers ever put into use, Boston is now a hub for biotechnology, robotics and artificial intelligence — though it’s also home to several B2B software giants. So it’s no surprise that the city consistently ranks among the greatest startup ecosystems in the world.
Key Facts About Boston Tech
- Number of Tech Workers: 269,000; 9.4% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: Thermo Fisher Scientific, Toast, Klaviyo, HubSpot, DraftKings
- Key Industries: Artificial intelligence, biotechnology, robotics, software, aerospace
- Funding Landscape: $15.7 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Summit Partners, Volition Capital, Bain Capital Ventures, MassVentures, Highland Capital Partners
- Research Centers and Universities: MIT, Harvard University, Boston College, Tufts University, Boston University, Northeastern University, Smithsonian Astrophysical Observatory, National Bureau of Economic Research, Broad Institute, Lowell Center for Space Science & Technology, National Emerging Infectious Diseases Laboratories










