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Jason Wilebski has worked in the education sector since 2003. Jason began their career as Director of Admissions at Kaplan University and then moved on to TuitionFit in 2019, where they served as the Vice President of College Partnerships. In this role, they identified and developed relationships with college admissions and financial aid teams to introduce recruiting advantage of TuitionFit. Jason then joined Path in 2020 as a Financial Aid Advisor. Currently, they are the Vice President of Business Development at ScholarshipOwl, a platform connecting students with scholarships. Over 8 million students have registered on the platform and it is growing by an average of 150K new signups per month.

Jason Wilebski received their Bachelor of Business Administration (BBA) from the University of St. Francis in 1990, majoring in Business, Management, Marketing, and Related Support Services. Jason then went on to receive their Masters in Business Administration, Management and Operations from Purdue University Global in 2005.