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Kyle Olmstead has a diverse work experience spanning different industries. Kyle started their career as a Human Resources Intern at Pinstripe in 2010. From there, they worked as Leadership Recruiting at Kohl's Department Stores from November 2010 to January 2012. In January 2012, they joined St. Charles Youth and Family Services as a Youth Employment Service Coordinator until September 2012.

Following that, Kyle joined Agile1 as a Manager, Client Services from September 2012 to January 2016. Kyle then worked as a Senior Manager, Client Services at Agile1 from January 2016 to May 2016.

In 2016, Kyle took on a role as Contingent Workforce Operations at Quad/Graphics from May 2016 to September 2016. Later that year, they returned to AgileOne and served as Regional Manager, Client Services from September 2016 to April 2018. Kyle was then promoted to Director, Client Services at AgileOne, and has been in that role since April 2018.

Most recently, Kyle joined CEO Insurance Services, LLC in August 2022 as an Independent Insurance Agent, specializing in Medicare and ACA Solutions in Wisconsin.

Kyle Olmstead obtained a Bachelor of Arts degree in Sociology from the University of Wisconsin-Milwaukee, where they studied from 2006 to 2010. In addition, they hold a certification as an Accident and Health Agent from the Office of Insurance Commission, although the exact date of this certification is not provided.