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Robert Claybrook has over three decades of experience in the technology industry. Robert began their career in 1988 as a Manager of Applications for Safelite AutoGlass. Robert then moved to EXPRESS in 1991, where they held the same role. In 1997, they became the Director of Information Technology for Treat Entertainment Inc. (Distributor to Wal-Mart). Robert then moved to J.Crew in 1998, where they held the same role. In 1999, they joined Bed Bath & Beyond, where they held the roles of Vice President - Chief Information Officer, VP - Information Technology, and Director - Information Technology. In 2018, they became President of Emergence of Tech. LLC., a strategic consulting firm focused on leveraging technology to drive business results. Most recently, in 2020, they became the Chief Technology Officer at Micro Strategies Inc., where they lead the strategy development and execution of the company's hybrid IT and managed services practice.

Robert Claybrook attended DeVry University.