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Abby Cheesman has a diverse work experience, beginning in 2007 when they were a Lead Teller at Wells Fargo Bank. In 2008, they were an Organizational Development Intern and a Technical Writer at The Chicago School of Professional Psychology. In 2009, they were a Research Intern at Platt Retail Institute. From 2010 to 2014, they were a Research Associate and Project Operations Fellow at gravitytank. Abby then co-founded and served as CFO of Skill Scout.

Abby Cheesman completed a Bachelor of Arts in Sociology/Psychology from the University of Northern Iowa in 2007. Abby then earned a Master of Arts in Industrial/Organizational Psychology from The Chicago School of Professional Psychology in 2010.