Richard Olsen is an accomplished IT Executive with over 20 years of leadership experience in infrastructure, operations, cybersecurity, and digital transformation. Currently serving as the Senior Director of Information Technology at Lessen, Richard has a proven track record of aligning technology initiatives with business goals, driving enterprise-scale improvements in performance and cost efficiency. Previously, they held key positions at Ryan Specialty Group, Florida Family Insurance, SMS Assist, LLC, and Grubb & Ellis Company, where they successfully managed extensive IT operations and implemented innovative infrastructure solutions. Richard earned a B.S. in Computer Information Systems and an M.B.A. in Business Administration from DeVry University and Keller Graduate School of Management, respectively.
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