Anderson started his career early at his father’s Ditch Witch dealership in eastern Wisconsin. While working in the Ditch Witch shop, Anderson attended college at UW-Platteville with an emphasis in engineering and business. His first position in sales was in the northern Wisconsin and the Upper Peninsula of Michigan.
Anderson worked briefly for a large utility contractor as a superintendent before he was offered a sales position at Vermeer Minnesota (RDO-Vermeer), learning a great deal about larger directional drills and the pipeline industry.
In 2004, with the help of a family member, he started Anderson Underground as a directional drilling contractor. Anderson sold his portion of the business in 2008. He went back to RDO-Vermeer and held a couple of different positions as Underground Specialist as well as Sales Manager.