Deidre has dedicated her career to community and small business development. In 2008 during her senior year of college, Deidre began her own small business. Caleo Enterprises provides entrepreneurs affordable marketing tools and business strategies to businesses and her work has impacted over 300 small businesses and nonprofit organizations in Iowa. In 2012, Deidre worked for President Barack Obama’s re-election campaign as the State African American Vote Director. Deidre developed and implemented a program that increased the proportion of African American voters in Iowa from 3% to 7% and registered historic numbers of African American voters. After 2012, Deidre went on to manage two victorious campaigns for Des Moines School Board. In 2005, Deidre co-founded Back 2 School Iowa, a non-profit dedicated to collaborating with communities and corporations in order to provide resources to inspire youth in continuing in their education and build their future careers.