Mutual Opportunities

Director, Enrollment Technology Strategy & Execution
Springfield, Massachusetts; Boston, Massachusetts; New York, New York
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
The Opportunity
As the Director of Enrollment Technology Strategy and Execution, you will lead the development and implementation of our long-term approach to enable a more efficient and effective enrollment technology eco-system, leading to improved results by leveraging both people and technology. You will achieve this by collaborating with internal partners to streamline processes and interactions; support new business development; achieve enrollment results; and facilitate product growth within existing clients. This individual will ensure the high-quality execution and leadership of technology supported business processes, data management, and systems management. Also, the individual will manage a team of people responsible for EDI production and producer support.
The Team
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 Director of Enrollment Technology Strategy and Execution, your responsibilities will include but are not limited to the following:
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 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
Embrace a culture of continuous improvement across the team and across the enrollment value stream
Ownership of end-to-end processing of enrollment data from enrollment platforms to administration platforms along with associated SLAs, data management, error management, continuous improvement and metrics.
Manage the EDI team, including development of performance metrics that the team will be measured against.
Ensure the team analyzes and develop specifications for EDI enhancements, automation and improvements.
Oversee the production support of existing EDI partners.
Manage the production environment and proactively prioritize, communicate, and resolve any EDI process or system issues.
Use access to data and personal observation to identify potential process improvement opportunities to enhance the efficiency of the EDI processes.
Direct cross-functional work, as needed, to improve processing timelines and success rates for processing of enrollments and associated demographic data through to certificate issuance.
The Minimum Qualifications
8+ years of Strategic Leadership experience, with a focus on enrollment platform technology and processes, product integrations, file formats, audit/test file feeds in combination with at least 2+ years of leading & managing people
2+ years of Insurance Industry experience with a focus on Insurance benefits and/or Group and Worksite benefits industry, competitors, products and services
The Ideal Qualifications
Demonstrated ability to work cross-functionally to reconcile competing priorities while meeting organizational objectives
Ability to interact with all levels of centers of influence both internally and externally (Benefits Producers/Enrollment Firms, key relationships, Committees/Trustees, etc.)
Advanced written and verbal communications skills
Decision making based on sound financial principles and knows when to engage with others to inform the decision (e.g. manager, peers, customers)
Demonstrates forward thinking; looking ahead to anticipate problems, and considers future impact of actions
What to Expect as Part of MassMutual and the Team
Regular meetings with the Enrollment Technology teams
Focused one-on-one meetings with your manager
Networking opportunities including access to Asian, Hispanic/Latinx, African American, women, LGBTQIA+, veteran and disability-focused Business Resource Groups
Access to learning content on Degreed and other informational platforms
Your ethics and integrity will be valued by a company with a strong and stable ethical business with industry leading pay and benefits
#LI-RS1
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.
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: $134,400.00-$176,400.00
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*
- 88% of employee respondents say they are proud to work at MassMutual
-
90
% of employee respondents say they feel encouraged to bring forth new ideas - 86% of employee respondents say MassMutual cares about and supports the well-being of their employees
*Source: 2024 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?
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