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Steve Olson has a diverse work experience that spans several industries and roles. Steve started their career as a Store Manager at Perry Restaurant Group in 1982, where they worked until 1986. Following this, they joined D&D Homes as a General Manager, a position they held for 14 years until 2000. In 2001, Steve joined Retail Search Group, a PrincetonOne Company, as a Strategic Recruiting Director, specializing in executive search for retailers nationwide. Steve filled positions in various departments including Finance, Accounting, Audit, Tax, and Business Development at Director, Vice-President, and C-Level roles. Steve remained with the company until 2019, when they retired. Subsequently, they took on the role of a Senior Executive Recruiter at PrincetonOne in 2020, and then continued this role at Job.com starting in 2023, where they are currently employed.

Steve Olson attended the University of Vermont from 1978 to 1982, where they obtained a Bachelor of Arts degree in Mathematics and a Bachelor of Arts degree in Economics. Prior to their university education, they attended Simsbury High School and Burr and Burton Seminary. Currently, they do not hold any additional certifications such as the Certified Senior Account Manager (CSAM).