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Rick Held began their work experience in 2003 as a Vice President at Affinity Direct, helping the company become the fourth largest federal student loan consolidation company in the US. Rick then joined Affinity Marketing Partners in 2003 as a Vice President and worked there until 2011. In 2008, Rick became the President & Co-Founder of Make The Web Better, a web search business. Rick later sold certain assets to InfoSpace. In 2012, Rick moved to Twill and held the positions of Chief Revenue Officer and Chief Experience Officer, where they focused on marketing, analytics, and user experience. Finally, in 2022, Rick became the Chief Operating Officer at Ai Media Group.

Rick Held attended the University of Wisconsin-Madison from 1999-2003, where they earned a Bachelor's degree in Consumer Affairs in Business. The field of study for their degree is not specified.