Rob Cleek

Chief Technology Officer - Employee Benefits at Brown & Brown

De Pere, Wisconsin, United States

About Rob Cleek

Rob Cleek is Chief Technology Officer - Employee Benefits at Brown & Brown. Location: De Pere, Wisconsin, United States.

With over 20 years of IT experience, I currently serve as Chief Technology Officer at Brown & Brown, driving innovation within the Employee Benefits sector. Collaborating with cross-functional teams, I focus on enhancing capabilities for key divisions like the National Pharmacy Team, PlanIT, and Winston Benefits, ensuring scalable, secure, and client-focused solutions. My role emphasizes aligning technology initiatives with the company's mission to meet evolving industry demands. Previously, as Vice President of Information Technology at PillarRx Consulting, I contributed to strategic planning and oversight across IT functions, including infrastructure, security, and development. My leadership fostered a culture of accountability and collaboration, empowering teams to deliver impactful results. Dedicated to leveraging technology to enable business growth, I bring a passion for aligning IT strategy with organizational goals.

Skills

  • Enterprise Software
  • Team Management
  • Change Management

Additional experience

  • Vice President Information Technology

    PillarRx Consulting

    June 2020 – June 2025

Education

  • Associate's degree, Northeast Wisconsin Technical College