Jon Cholak is an investment director on the ventures team at USAA. Jon focuses primarily on investments in enterprise software, artificial intelligence, security and data analytics.  Jon represents USAA on the boards of directors for Roostify, Robin Systems, CafeX Communications, Gridspace, Lightbend, Context360 and PrecisionHawk.  Jon previously served on the boards of Saffron Technology (acquired by Intel) and Automatic Labs (acquired by SiriusXM).

Prior to joining USAA, Jon worked for Intel Corporation and Deloitte Consulting, LLP. While at Intel, Jon managed a portfolio of early-stage internal ventures designed to provide non-core organic revenue growth. During his tenure at Deloitte Consulting, Jon worked with numerous private and public sector clients concentrating on strategic management, process reengineering, and systems modernization and integration.

Jon holds a Bachelor of Science in Information Systems and International Business from New York University, an MBA from The University of Texas at Austin.