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Head of Worksite Technology

Springfield, Massachusetts Technology Job ID R14258

The Head of Worksite Technology will be responsible for a broad and critical technology portfolio that enables MassMutual’s Worksite business to scale and compete in the Group Whole Life and Voluntary Benefits marketplace. 
As part of the broader leadership team you will partner with your peers to deliver exceptional technology solutions for MassMutual 
This individual will leverage their process-driven, analytical, technical, and financial management skills to create and maintain solutions, which include defining, designing, developing, implementing, and maintaining solutions, in a rapid, iterative project delivery environment. They will lead a large team in partnering with business counterparts to understand their needs and drive forward innovative, scalable, and robust solutions.
As the lead of this function, you will have the opportunity to:
•    Drive continuous improvement and modernization of our worksite systems
•    Design and deliver data integrations with partner firms who administer the business
•    Develop digital solutions that drive forward our enterprise digital transformation
•    Foster an inclusive culture that values engineering excellence and innovation

The Team
The Worksite Technology team consists of an international group of developers, architects, engineers, analysts, testers and project managers focused on delivering software solutions through waterfall and agile methodologies.

The Impact

Business & Technology Strategy Alignment

  • Partner with business leaders in the establishment and growth of programs enabling business growth, cost optimization, and/or resolution of business problems through the use of appropriate technology solutions
  • Become and remain well versed in Worksite business and related challenges across the organization
  • Participate as member of the management team that develops strategies for the larger organization
  • Collaborate with product owners, business leadership, architects, developers and vendors to ensure program strategy and execution align with business needs
  • Support customer engagement, financial management, sustainable business growth, profitability, compliance, and operational efficiencies through effective application of solutions

Technical Alignment

  • Work with the Enterprise Architecture team to ensure appropriate patterns are implemented in solutions
  • Ensure all solutions are secure and aligned to all security and compliance requirements
  • Collaborate across ETX to deliver solutions that require input and cross-team delivery in service of Distribution requirements

People & Program Management

  • Select, manage, develop, coach, and motivate staff members
  • Contribute to the development of financial and resource planning needed to achieve department business objectives
  • Raise risks and issues and serve as program primary point of escalation
  • Remove barriers to enable the team to complete objectives; drive and influence decisions

General Leadership

  • Operate independently on multiple program tasks and varied complexities
  • Support and drive change management of existing processes
  • Stay abreast of emerging trends in technology and the external environment

The Minimum Qualifications

  • Bachelor’s degree in Information technology, Computer Science or related field.
  • 10+ years of related experience with at least 5+ years of technical leadership.
  • Proven ability to translate business strategy into cohesive technology strategy and corresponding delivery roadmaps.
  • Proven ability to successfully manage large vendor relationships.
  • Uniquely skilled at communicating with executive level leaders.
  • Demonstrate success is having difficult conversations with vendors and stakeholders.
  • Curious learning with a track record of using the knowledge to drive improvements.
  • Deep technical knowledge in application development.
  • Identifiable track record of leading/driving key initiatives working with cross functional teams to successfully implement critical business projects, problem solutions and continuous improvement efforts.

The Ideal Qualifications

  • Experience managing teams delivering worksite related solutions.
  • Knowledge of the worksite or other group-oriented business.
  • Proficient with project management tools and techniques, such as Jira, Confluence, Microsoft Project, Scrum and Kanban


Salary Range: $172,000.00-$225,700.00 Apply

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.

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About MassMutual®

At MassMutual, we believe in the value of being together in our offices and in personal flexibility.

Our work environment is one where the majority of our team members work a hybrid schedule — working at least three days in the office (Tuesday, Wednesday and a third day) and the rest remotely, balancing flexibility with in-person collaboration. While the majority of our employees follow this hybrid model, some of our roles continue to be 100% on-site and others may be 100% remote, subject to business needs.

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, policyowners and customers, 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.

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