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Toby Pennycuff is an experienced EVP, CIO at Hilltop Holdings, Inc., where Toby provides strategic vision and leadership in the development and implementation of enterprise-wide IT solutions. With a background in Fortune 100 companies and the DoD space, Toby also owns and operates PennMann Technology, L.L.C., providing IT executive leadership services and consulting. Previously, Toby has held CIO positions at companies like Essex Property Trust and JCPenney, showcasing their expertise in transforming IT organizations and leading large-scale systems design efforts. A BBA graduate from Texas McCombs School of Business, Toby has a proven track record in the IT consulting and technology sector.