Technology Lead - Project Manager; Life Insurance Worksite Program

Technology Lead – Project Manager

Location:

Springfield, MA

Employment Type:

Contract (12 Months) Target

Start Date:

June 18, 2026 Experience

Required:

8–10 Years

Interview Process:
In-Person

Required

Position Overview:

We are seeking an experienced Technology Lead / Project Manager to lead the day-to-day delivery of a Life Insurance Worksite Program. The ideal candidate will have a strong background in technology project management within the insurance industry, with proven expertise in driving execution, managing stakeholders, mitigating risks, and ensuring successful delivery of cross-functional initiatives. This role requires a proactive, self-driven leader who can create alignment across business and technology teams, maintain governance standards, and deliver clear communication on project status, risks, and dependencies.

• Lead end-to-end project delivery for the Life Insurance Worksite program, ensuring alignment with business objectives and timelines.
• Develop and manage project plans, schedules, milestones, and deliverables across multiple teams.
• Establish and maintain project governance, ensuring transparency and accountability throughout the project lifecycle.
• Coordinate cross-functional teams, including business stakeholders, technology teams, vendors, and leadership.
• Identify, assess, and proactively manage project risks, issues, dependencies, and mitigation strategies.
• Drive executive-level status reporting, project communications, and governance meetings.
• Remove blockers and facilitate timely decision-making to keep projects on track.
• Monitor project progress, ensure adherence to quality standards, and support successful implementation activities.
• Collaborate with release management teams to coordinate deployment and cutover activities when required.
• Promote best practices in project management and continuous process improvement.

• 8–10 years of experience managing complex technology projects or programs.
• Proven experience delivering projects within the insurance domain, preferably supporting life insurance or employee benefits initiatives.
• Strong understanding of project governance, stakeholder management, risk management, and dependency tracking.
• Demonstrated ability to lead cross-functional teams and drive execution in fast-paced environments.
• Excellent communication, presentation, and executive reporting skills.
• Strong organizational, analytical, and problem-solving abilities.
• Ability to work independently while maintaining accountability for project outcomes.

• Experience with insurance platforms such as:
• EIS
• Guidewire
• Duck Creek
• Similar policy administration systems
• Experience delivering supplemental insurance or voluntary/worksite benefits programs.
• Experience supporting release management and cutover activities in regulated environments.
• Familiarity with Agile, Waterfall, or hybrid project delivery methodologies.
• Project Management Professional (PMP) certification or equivalent project management credentials.