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.

Matt delivered a comprehensive service and solution to us, on time, and very professionally. We were delighted with his service, and his knowledge helped us understand exactly what was on the table. Thanks again

Andrew Brummer

Matt delivered a comprehensive service and solution to us, on time, and very professionally. We were delighted with his service, and his knowledge helped us understand exactly what was on the table. Thanks again

Andrew Brummer

Matt delivered a comprehensive service and solution to us, on time, and very professionally. We were delighted with his service, and his knowledge helped us understand exactly what was on the table. Thanks again

Andrew Brummer

Matt delivered a comprehensive service and solution to us, on time, and very professionally. We were delighted with his service, and his knowledge helped us understand exactly what was on the table. Thanks again

Andrew Brummer

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