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Ryan Oleson has a diverse work experience with a focus on sales and account management. Ryan started their career at Menards in 2002 as an Outside Sales Representative, where they worked until 2005. After that, they joined MidAm Building Supply as a Sales representative for a year. In 2006, they joined KPI Concepts, Inc as an Account Manager and worked there for 15 years until 2021. During their tenure at KPI Concepts, they also held the role of Division Manager from 2019 to 2021. In October 2021, they became the Vice President of Sales at KPI Concepts.

Ryan Oleson attended Lincoln Christian College from 1994 to 1998, but did not receive a degree or specify a field of study. From 2000 to 2001, they pursued a technical certificate in Heating and Air Conditioning at an unspecified technical institute.