Project/Program Manager

Role : Project/Program Manager

Location: Candidate has to work 3 days in Boston office or in Spring Field office, MA

JD for the Project/Program Manager:

Lead day-to-day delivery for the Worksite program by driving schedule, governance, and cross-functional execution. This role requires strong stakeholder management, proactive risk and dependency handling, and crisp reporting.
The ideal candidate is a self-directed, action-oriented project leader who creates clarity, removes blockers, and keeps teams accountable.

Key Responsibilities

• Own and maintain the integrated delivery plan (milestones, dependencies, sprint/release calendar, and key deliverables).
• Run delivery governance: workstream syncs, RAID management, decision and action tracking, and release readiness cadence.
• Proactively identify and manage risks, issues, and dependencies, drive mitigation plans and escalations with recommended actions.
• Coordinate across product, business, engineering, QA, and environment/release teams to ensure aligned execution.
• Manage scope alignment and change control by documenting impacts to timeline, cost, and deliverables.
• Produce executive-ready status reporting (weekly status, milestones, KPIs, forward look, and support requests).
• Facilitate stakeholder communications and ensure timely decisions to avoid delivery delays.
• Support cutover and go-live planning (readiness checklists, runbook coordination, and go/no-go inputs).

Must-Have Qualifications

• 8+ years of project management experience delivering technology programs; insurance domain experience required.
• Strong understanding of insurance products and operations.
• Demonstrated success managing cross-functional delivery with multiple workstreams and vendor/onshore/offshore teams.
• Strong governance discipline (RAID, action/decision logs, dependency management) and ability to operate with minimal direction.
• Excellent written and verbal communication; ability to produce concise, leadership-ready updates.
• Experience with Agile, Waterfall, or hybrid delivery methods; comfort operating in ambiguity and evolving priorities.

Nice-to-Have Qualifications

• Exposure to insurance platforms (EIS, Guidewire, Duck Creek, or similar).
• Experience delivering supplemental or voluntary benefits (Worksite programs).
• Experience supporting release/cutover activities in regulated environments.

Behavioral Expectations (Critical)

• Highly proactive and action-oriented; does not require repeated follow-ups.
• Owns outcomes end-to-end and escalates risks early with options and recommendations.
• Strong stakeholder presence; communicates clearly, calmly, and consistently.
• Disciplined progress reporting and transparent status; no surprises.

Tools / Technology (Preferred Exposure)

• Jira, Confluence (or equivalent backlog/documentation tools).
• MS Project, Smartsheet, or equivalent planning tools.
• Microsoft Teams and standard collaboration tools.