The IT Project Manager II will lead and support complex cross-functional initiatives that advance the company's modernization of core insurance systems and digital platforms. Additionally, 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 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.

Essential Duties & Responsibilities

Project Leadership & Delivery

• Lead Duck Creek Upgrade for Coverys, through all stages of execution. This is a strategic priority for Coverys.
• 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.
• For the assigned projects, ensure that UAT coordination, release readiness and production cut over is occurring effectively, 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

• In addition to Duck Creek upgrade, 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, 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.
• Lead ongoing Duck Creek releases and ongoing monthly upgrades. Evaluate release notes and reach out to UW, Claims and Finance, went through DC changes and figure out what to be put in release.
• Provide project management for other initiatives as needed across the enterprise.

Governance & Compliance

• Adhere to Coverys standards, audit, and compliance requirements.
• Manage change control, documentation, and traceability for compliance.
• Be the point person for DCOD Platform Governance including activities below:
  
  • Engage with Duck Creek to request and review pre-upgrade analysis reports, which provide an assessment of organizational readiness, technical upgrade estimates, and a list of cloud optimization backlog items to be addressed.
  • Ensure the organization leverages out-of-the-box Duck Creek functionality wherever possible to reduce customization debt and streamline future upgrades.
  • Monitor and govern the level of customization against the base Duck Creek configuration, flagging deviations that could introduce upgrade complexity or compatibility risk.
  • Oversee environment dependencies across DCOD teams, ensuring 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 & 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).
• Lead end to end delivery of DuckCreek implementations, upgrades, and enhancements (Policy, Billing, Claims, Rating)
• Manage Vendor relationships and SOWs with Duckcreek or System Integrator partners.

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.
• 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.

Education, Experience, Competencies & Values

Required:

• Bachelor's degree in business, Computer Science, or related field
• 5+ years of experience in IT project management, with at least 4 years of delivering projects using Duck Creek technologies.
• Leading Duck Creek upgrade project and other Duck Creek related initiatives that require 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

Preferred:

• 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.

Core Competencies:

• 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

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.