Who We Are  |   Leadership  |   Toby Pennycuff

Toby Pennycuff

Chief Information Officer
Hilltop Holdings

As Chief Information Officer, Mr. Pennycuff coordinates and oversees the development and implementation of all information technology. Mr. Pennycuff’s strategic vision and leadership ensures that Hilltop’s technology initiatives continue to provide business value, support the firm’s core mission, and effectively manage technology and security risks.


Career Highlights

  • Appointed chief information officer of Hilltop in May 2017
  • Formerly head of information technology at Essex Property Trust
  • 40+ years in the information technology industry
  • Has held various senior IT leadership positions for several other companies, including EDS (acquired by Hewlett Packard in 2008), JC Penney and PennMann Technology


  • B.B.A. in Statistics and Operations Research, University of Texas at Austin

Past Affiliations

  • IBM Power Systems Board of Advisors
  • University of Texas at Dallas Jindal School of Business IT Industry Advisory Board
  • University of Texas at Austin McCombs School of Business Information Management Advisory Council
years of information technology experience
years with Hilltop Holdings
IT employees on staff
"To recognize that the greatest error is not to have tried and failed, but that in trying, we did not give it our best effort."
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