IT Project Manager II

About the role

Lead and support complex cross-functional initiatives that advance the company’s modernization of core insurance systems and digital platforms. Establish 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 IT Project Manager II has a solid 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.

Responsibilities

• Project Leadership & Delivery
  • Lead Duck Creek Upgrade for Coverys through all stages of execution as a strategic priority.
  • Manage all aspects of project delivery—scope, schedule, cost, risks, and dependencies.
  • 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.
  • Ensure effective UAT coordination, release readiness, and production cutover, including stakeholder sign-off, operational preparedness, communications, validation steps, contingency planning, and post-release support.
  • Develop and track project-level UAT and release readiness plans, including milestones, dependencies, timelines, risks, responsibilities, and approvals.
  • Facilitate post-release reviews to capture lessons learned and improve future project execution.
  • Provide project management for other initiatives as needed across the enterprise.
• Duck Creek Monthly Upgrade Coordination
  • Serve as the primary point of contact between Coverys and Duck Creek Technologies for all monthly platform releases and upgrade cycles on Duck Creek OnDemand (DCOD).
  • Collaborate with Duck Creek's assigned service managers in monthly one-on-one meetings to review SLA reports, open incident tickets, upcoming release schedules, and business operational goals.
  • Review Duck Creek's monthly release notes and assess the impact of new features, hot fixes, and platform changes on existing configurations across Policy, Billing, Claims, and Rating modules.
  • Maintain an internal upgrade calendar and coordinate readiness across development, QA, and business teams well ahead of each release window.
  • Track and manage the cloud optimization backlog, prioritizing remediation items identified by Duck Creek between monthly upgrade cycles.
  • Evaluate release notes and collaborate with Underwriting, Claims, and Finance to determine necessary changes for each release.
• Governance & Compliance
  • Adhere to Coverys standards, audit, and compliance requirements. Manage change control, documentation, and traceability for compliance.
  • Serve as the point person for DCOD Platform Governance, including:
    • Engaging with Duck Creek to request and review pre-upgrade analysis reports assessing organizational readiness, technical upgrade estimates, and cloud optimization backlog items.
    • Ensuring the organization leverages out-of-the-box Duck Creek functionality to reduce customization debt and streamline future upgrades.
    • Monitoring and governing customization levels against the base Duck Creek configuration, flagging deviations that could introduce upgrade complexity or compatibility risk.
    • Overseeing environment dependencies across DCOD teams to ensure infrastructure, integrations, and security configurations are aligned before each upgrade window.
• Change Management & Adoption
  • Develop and execute change management strategies to ensure successful adoption of new systems, processes, and technologies.
  • Partner with IT and business leads 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) and IT delivery teams for strategic multi-year initiatives.
  • 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).
  • Lead end-to-end delivery of Duck Creek implementations, upgrades, and enhancements (Policy, Billing, Claims, Rating).
  • Manage vendor relationships and SOWs with Duck Creek or system integrator partners.
• Continuous Improvement
  • Establish project management delivery standards for the IT organization and own best practices, guiding and coaching leaders in their use.
  • Contribute to Agile transformation efforts and continuous improvement of project governance.
  • Promote a culture of transparency, accountability, and servant leadership.

Requirements

• Bachelor’s degree in business, Computer Science, or related field.
• 5+ years of experience in IT project management, with at least 4 years delivering projects using Duck Creek technologies.
• Experience leading Duck Creek upgrade projects and other Duck Creek-related initiatives requiring in-depth knowledge and partnership with Duck Creek.
• 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.
• Eligible to work in the US without sponsorship or restriction.

Preferred Qualifications

• PMP certification or Agile Project Management (PMI-ACP).
• Experience with 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.

Skills

• Structured Project Coordination
• Strategic Delivery & Execution Excellence
• Business and Technical Agility
• Change Management
• Risk, Budget, and Vendor Management
• Stakeholder Influence and Communication
• Servant Leadership and Coaching Mindset
• Continuous Improvement Orientation

Pay

The base salary range for this role is $107,500 - $144,700. Individual compensation packages are based on a variety of factors that are unique to each candidate including geographic location, skill set, experience, qualifications, and education.