Harry Reagan

About Harry Reagan

With 25+ years as a technology executive, I have led complex IT development projects and vendor software implementations across claims, private banking, investment services, retail banking, risk management, and operations. My core strengths include technology governance, process improvement, large-scale implementations, contract negotiation, and third-party management.Currently, I serve as Claims IT – Shared Services General Manager, leading teams that support the Claims business in payments, mainframe, vendor management, and frameworks. These teams deliver payments, data, structure, and vendor expertise to ensure operational efficiency across Claims applications.Previously at Progressive Insurance, I was IT Sourcing Manager, leading contract negotiators handling all software and telecom agreements—an annual spend of $400M with strong year-over-year growth. I built strong partnerships with Business, Legal, Risk, Finance, and Information Security, ensuring IT sourcing was engaged early in vendor discussions to optimize cost, compliance, and performance.As SVP of Technology at KeyBank, I directed development, implementation, and support for retail, wealth management, and business banking. I also managed all IT and operations contracts and vendor relationships, aligning technology strategy with business goals to deliver measurable value and ensure compliance. My teams supported systems such as Salesforce, FIS Global Plus, Charles River Everywhere, and Archer GRC. I emphasized mentorship, empowering project managers, developers, and analysts to deliver high-quality solutions.In my prior role as SVP of Procurement at KeyBank, I led strategists and analysts overseeing all IT, Operations, and Commercial Bank contracts and vendor relationships. Responsibilities included RFP management, vendor selection, negotiations, third-party risk management, and ongoing vendor performance. This work drove cost savings, stronger vendor partnerships, and consistent risk oversight.

Experience

1. Claims IT Group Manager

   Progressive Insurance

   Jan 2025 — Present · Cleveland, OH, US

   I lead the Shared Services team within Claims IT, supporting our Claims business. Claims IT Shared Services provides First Notice of Loss(FNOL) teams with the tools, technology, and support needed to streamline claim intake processes, including FNOL platforms, automation, data integration, and communication tools- We ensure systems are secure, scalable, and compliant while offering training, AI-driven enhancements, and disaster recovery solutions to improve efficiency and customer experience. We also ensure our mainframe back end is operating effectively and efficiently to provide data to various downstream teams- Shared Services may not have a singular, high-profile project, but we play a crucial role in supporting major initiatives, by providing the integration, data, and tools needed to our other systems. We also are responsible for all aspects of payments related to claims- Working behind the scenes, we provide essential support to Claims IT, Claims, CRM, and Corporate

Education

• Baldwin Wallace University

  EMBA, Masters of Business Administration in Executive Management

  2006 — 2008

• John Carroll University

  Industrial/ Organizational Psychology, Business Management

  1995 — 1999

• St. Ignatius High School

  College Prep

  1991 — 1995

Skills

• IT Strategy
• Business Strategy
• Vendor Management
• Leadership
• Business Process Improvement
• Banking
• Risk Management
• Requirements Gathering
• Project Management
• Business Analysis
• IT Management
• Process Improvement
• Management
• Portfolio Management
• Project Planning
• Sdlc
• Program Management
• Testing