Technology Lead - Project Manager (Life Insurance Worksite Program)

Technology Lead – Project ManagerLocation: Springfield, MA Employment Type: Contract (12 Months) Target Start Date: June 18, 2026 Experience Required: 8–10 YearsInterview Process: In-PersonRequired 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.Key ResponsibilitiesLead 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.Required Qualifications8–10 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.Preferred QualificationsExperience with insurance platforms such as:EISGuidewireDuck CreekSimilar policy administration systemsExperience 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.