Senior Guidewire Program Manager

HDI Global Insurance Company; Chicago (IL); On-site; USD 160,000 - 185,000; Full time

Benefits offered by this job

401(k) with company match

Paid Time Off

Medical

Health Reimbursement Arrangement (HRA)

Telemedicine

Wellness Program

Employee Assistance Program (EAP)

Dental

Vision

Life Insurance

Short- and Long-Term Disability

Transit and Parking benefits

Job summary

HDI Global Insurance Company is seeking a seasoned Guidewire Project Manager in Chicago to lead the PolicyCenter implementation (Program TOPSPIN). You will coordinate with business stakeholders, IT teams, SI partners, and vendors to ensure on-time, on-budget delivery across multiple releases.

The role emphasizes risk management, quality assurance, change management, and governance, with a focus on regulatory compliance and data protection throughout the project lifecycle.

Qualifications

• Bachelor’s degree in Information Technology, Business Administration, Project Management, or a related field; a Master’s degree is a plus.
• 7+ years of experience managing IT projects, with at least 3 years focused on Guidewire implementations (PolicyCenter, BillingCenter, ClaimCenter, or Guidewire Rating).
• Strong project management skills, with a proven record of planning, executing, and closing complex projects on time and within budget; strong Agile/Scrum experience.
• Guidewire certification or experience with Guidewire SurePath methodology and the Guidewire Testing Framework is strongly preferred; PMP or equivalent certification is a plus.
• Knowledge of insurance business processes, especially underwriting, policy administration, claims, and billing (commercial P&C strongly preferred).
• Effective verbal and written communication skills, with the ability to convey complex information to both technical and non-technical stakeholders, including executive presence.

Responsibilities

• Lead end-to-end planning and execution of the Guidewire PolicyCenter implementation — defining scope, goals, deliverables, timelines, and resource requirements; establish and manage project plans, milestones, and dependencies in alignment with Guidewire’s SurePath delivery methodology.
• Serve as the primary point of contact for stakeholders, facilitating communication across business units, IT teams, and vendors; conduct regular status meetings, including monthly Steering Committees, and provide transparent progress and financial reporting.
• Work with the CITO and Head of Business Transformation to allocate resources effectively and manage project budgets, staffing, and timelines; monitor expenses against plan and manage discretionary budget against System Integrator requests for unplanned work.
• Identify risks and develop mitigation strategies; resolve project issues, escalating to senior management when necessary; ensure the implementation complies with regulatory requirements, data protection standards, and internal policies.
• Coordinate with Guidewire, the System Integrator, and internal QA teams to develop test plans and validate the implementation; oversee UAT, and ensure sprint, smoke, performance, and stabilization cadences, including business process and model-office testing where appropriate.
• Partner with the OCM Lead on future-state process flows, user-impact documentation, training materials, and communication plans; organize and conduct training to drive end-user adoption of new Guidewire features and functionality.
• Alongside the implementation, work with IT Governance to establish and mature project and portfolio management capabilities across the IT organization, providing guidance on portfolio steering cadences.
• Collaborate with System Integrator project management for Guidewire development while independently managing non-Guidewire workstreams and integrations to core systems (e.g., billing, CRM, data platform).

Skills

Project management

Agile/Scrum

Guidewire

Communication

Education

Bachelor's degree

Master's degree

Tools

Jira/Confluence

SharePoint

Microsoft Office Suite

Teams

Job description

HDI Global Insurance Company is seeking a seasoned Guidewire Project Manager in Chicago to lead the PolicyCenter implementation (Program TOPSPIN). You will coordinate with business stakeholders, IT teams, SI partners, and vendors to ensure on-time, on-budget delivery across multiple releases.

The role emphasizes risk management, quality assurance, change management, and governance, with a focus on regulatory compliance and data protection throughout the project lifecycle.