Dean Oswald earned a bachelor's degree in animal science from Western Illinois University, a master's degree in agriculture education from Southern Illinois University, and a master's degree in agronomy from the University of Illinois.

Oswald is a member of the National Association of County Agricultural Agents (NACAA), the Illinois Extension Agricultural Association (IEAA), and the Illinois Forage and Grassland Council. Oswald has served as President of the Illinois Forage and Grassland Council, and is on the Board of Directors for the Illinois Grazingland Conservation Initiative. Dean is a (Certified Grassland Professional) with the American Forage and Grassland Council.

Osward earned the University of Illinois Extension Award of Excellence-Team Program, the National Association of County Agricultural Agents North Central Regional Winner Resource Manual 2002 Team and the Poster Presentation 2002 Team Awards, the Cooperative Extension Service sustained Excellence Award and the National Association of County Agricultural Agents Distinguished Service Award. Oswald was presented the Merit Award from the American Forage and Grassland Council in San Antonion, Texas in 2006.