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Ryan Kennedy began their work experience in 2006 at Best Buy as a Sales Representative, where they assisted customers and contributed to the training of new employees until 2009. From 2006 to 2011, they also worked as a Program Director at Arrowhead Bible Camp, overseeing daily programs and guiding staff members. In 2012, they joined the County of La Crosse Health and Human Services as an Economic Support Specialist, helping clients navigate and troubleshoot cases related to state economic assistance. In 2015, they became an IT Support Specialist at Reinhart Foodservice, providing technical support until 2018. Currently, they work at Pivot Group as a Web Project Manager, a position they have held since April 2019.

Ryan Kennedy attended Onalaska High School from 2001 to 2005. After completing high school, they pursued a Bachelor of Science degree in Business Administration and Management, General from the University of Wisconsin-La Crosse, from 2006 to 2010. In 2011, Ryan obtained a Certificate of Computer Hardware from Western Technical College.