Robert Sheeshley
CIO | CISO | CDAIO | 2024 Global CIO 100 | 2023 Georgia CIO of The Year | Board Member | Private Equity Advisor
Robert Sheesley is an award-winning technology executive and former Fortune 500 and private equity CIO with a proven record of scaling platforms to drive enterprise growth and shareholder value. He has led large-scale digital transformations and over one hundred M&A transactions supporting revenues exceeding $40B. As CIO of Wrench Group, he architected the technology foundation that enabled growth from $250M to over $2B. A U.S. Marine Corps veteran, Robert brings a disciplined, mission-driven approach to executive leadership, aligning technology strategy with business outcomes and long-term enterprise value.
Chief Information Officer (CIO)
Chief Data & AI Officer (CAIO)
Executive Technology Leader
Board Member & Advisor
About
Robert Sheeshley
Robert Sheesley is a dynamic, award-winning senior executive recognized for architecting and leading technology-enabled organizations through periods of rapid growth and transformation. He has deep expertise in digital strategy, mergers and acquisitions, enterprise architecture, and organizational change leadership. Robert has led hundreds of M&A transactions, including complex due diligence, carve-outs, and post-merger integrations across healthcare, manufacturing, retail, insurance, and home services. As CIO of Wrench Group, he built a scalable technology ecosystem supporting over 30 brands across 14 states. His leadership has been instrumental in enterprise data strategy, cybersecurity, digital commerce, and supply chain optimization. Robert is also a co-author of the Amazon best-selling leadership anthology Wired for Success and is known for strong C-suite and board-level collaboration.