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Director, Enrollment Technology Strategy & Execution

MassMutual

MassMutual

Software Engineering, IT, Data Science
Springfield, MA, USA · Boston, MA, USA · New York, NY, USA
USD 134,400-176,400 / year
Posted on Aug 21, 2025

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

Salary Range:

$134,400.00-$176,400.00

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.

Why Join Us.

We’ve been around since 1851. During our history, we’ve learned a few things about making sure our customers are our top priority. In order to meet and exceed their expectations, we must have the best people providing the best thinking, products and services. To accomplish this, we celebrate an inclusive, vibrant and diverse culture that encourages growth, openness and opportunities for everyone. A career with MassMutual means you will be part of a strong, stable and ethical business with industry leading pay and benefits. And your voice will always be heard.

We help people secure their future and protect the ones they love. As a company owned by our policyowners, we are defined by mutuality and our vision to put customers first. 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. At MassMutual, we Live Mutual.

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.