Senior IT Project Manager

ProSelect Insurance Company•Boston, MA

14d

About The Position

The Senior IT Project Manager will lead complex cross-functional initiatives that advance the company’s modernization of core insurance systems, digital platforms, and enterprise analytics capabilities. In addition to leading high-profile initiatives, this role will establish a traditional project management discipline, organizational change management, and Agile delivery practices to ensure technology programs are executed efficiently, within scope and budget, and aligned with Coverys’ mission to support the healthcare community through innovative insurance and risk management solutions. The Senior IT Project Manager has a deep understanding of standard project and change management practices required to successfully execute technology initiatives, excels at stakeholder management, and can bridge the gap between business and technology teams in a dynamic, compliance-driven environment. Essential Duties & Responsibilities: Project Leadership & Delivery Lead multiple mid-to-large scale projects across insurance technology portfolios (e.g., policy administration, billing, claims, cloud migrations, risk analytics, or digital experience). Manage all aspects of project delivery — scope, schedule, cost, risks, and dependencies — using Agile or Waterfall approach where appropriate. Collaborate with Product Owners and Scrum Leads to plan sprints, track delivery progress, and ensure alignment with business priorities. Maintain detailed project plans, RAID logs, and executive dashboards to ensure transparency and accountability. Drive decision-making and issue resolution across business, IT, and vendor teams. Change Management & Adoption Develop and execute change management strategies to ensure successful adoption of new systems, processes, and technologies. Partner with IT & business leads on projects to assess organizational readiness and stakeholder impact. Create communication, training, and engagement plans that minimize resistance and accelerate adoption. Support end-user enablement through targeted education, feedback loops, and reinforcement mechanisms. Measure adoption and effectiveness, capturing lessons learned for continuous improvement. Stakeholder Engagement Serve as the primary liaison between business units (Underwriting, Claims, Finance, Risk, Operations) for strategic multi-year initiatives and IT delivery teams. Prepare executive updates, steering committee materials, and project status reports highlighting key metrics and risks. Ensure effective communication and alignment among cross-functional stakeholders. Financial & Vendor Management Develop and manage project budgets, forecasts, and resource plans. Oversee deliverables, SOW compliance, and partner performance (e.g., system integrators, software vendors). Governance & Compliance Adhere to Coverys standards, audit, and compliance requirements. Manage change control, documentation, and traceability for compliance. Continuous Improvement Establish project management delivery standards for the IT organization & own the best practices required, guiding and coaching leaders (both business and IT) in use of those standards. Mentor Scrum Leads on delivery best practices. Contribute to Agile transformation efforts and continuous improvement of project governance. Promote a culture of transparency, accountability, and servant leadership. Perform other duties, as assigned.

Requirements

Bachelor’s degree in business, Computer Science, or related field
8+ years of experience in IT project management, with at least 4 years of delivering projects in an insurance or financial services environment.
Proven track record of leading Agile or hybrid projects involving multiple teams and vendors.
Demonstrated experience with organizational change management or business transformation initiatives.
Deep understanding of insurance processes — Policy, Billing, Claims, Underwriting, and/or Risk.
Strong proficiency with project and Agile management tools

Nice To Haves

PMP certification or Agile Project Management (PMI-ACP).
Experience with Duck Creek, Guidewire, Workday, Salesforce, or Data Warehouse programs.
Familiarity with cloud-based transformation, data governance, and compliance.
Excellent communication, facilitation, and leadership presence with executive audiences.

Responsibilities

Project Leadership & Delivery Lead multiple mid-to-large scale projects across insurance technology portfolios (e.g., policy administration, billing, claims, cloud migrations, risk analytics, or digital experience).
Manage all aspects of project delivery — scope, schedule, cost, risks, and dependencies — using Agile or Waterfall approach where appropriate.
Collaborate with Product Owners and Scrum Leads to plan sprints, track delivery progress, and ensure alignment with business priorities.
Maintain detailed project plans, RAID logs, and executive dashboards to ensure transparency and accountability.
Drive decision-making and issue resolution across business, IT, and vendor teams.
Change Management & Adoption Develop and execute change management strategies to ensure successful adoption of new systems, processes, and technologies.
Partner with IT & business leads on projects to assess organizational readiness and stakeholder impact.
Create communication, training, and engagement plans that minimize resistance and accelerate adoption.
Support end-user enablement through targeted education, feedback loops, and reinforcement mechanisms.
Measure adoption and effectiveness, capturing lessons learned for continuous improvement.
Stakeholder Engagement Serve as the primary liaison between business units (Underwriting, Claims, Finance, Risk, Operations) for strategic multi-year initiatives and IT delivery teams.
Prepare executive updates, steering committee materials, and project status reports highlighting key metrics and risks.
Ensure effective communication and alignment among cross-functional stakeholders.
Financial & Vendor Management Develop and manage project budgets, forecasts, and resource plans.
Oversee deliverables, SOW compliance, and partner performance (e.g., system integrators, software vendors).
Governance & Compliance Adhere to Coverys standards, audit, and compliance requirements.
Manage change control, documentation, and traceability for compliance.
Continuous Improvement Establish project management delivery standards for the IT organization & own the best practices required, guiding and coaching leaders (both business and IT) in use of those standards.
Mentor Scrum Leads on delivery best practices.
Contribute to Agile transformation efforts and continuous improvement of project governance.
Promote a culture of transparency, accountability, and servant leadership.
Perform other duties, as assigned.