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Woodson Hobbs has an extensive work experience, beginning in 2010 when they worked as a Consulting Executive for Woodson M. Hobbs and Associates. In 2011, they joined Crowdflower, Inc. as President and CEO. In 2012, they returned to Woodson M. Hobbs and Associates as Managing Director. In 2013, they became a Partner, Board and Executive Advisor for Newport Board Group. In 2016, they joined Firepoint Solutions, Inc. as Board Director and Palmarès Advisors as Managing Director. In 2018, they became Consulting Chief Operating Officer for CAST Services, LLC and Ownership Financial, Mortgage and Insurance Companies. Finally, in 2022, they began working as Chief Operating Officer for Woodson Banks.

Woodson Hobbs attended Wabash College from 1964 to 1966, where they studied Economics. Woodson then attended Purdue University from 1967 to 1969, where they studied Computer Science (Math).