Prior to joining the Denver Newspaper Agency, Whipple served two years as President and CEO of the Newspaper Agency Corporation in Salt Lake City, a JOA that manages business and production operations for the Salt Lake Tribune and Deseret Morning News. From 1992 to 2003, Whipple served as president and publisher of The Cincinnati Enquirer, which is managed under a joint operating agreement with The Cincinnati Post. In addition, he served as president of Tucson Newspapers Inc., a third JOA in his background. He began his career at his family's newspapers in Arkansas and Indiana.

Whipple has a distinguished record of community work and has served as chair and co-chair of several boards and committees that serve the public interest. Among others, he has held leadership positions with chambers of commerce and the United Way, as well as organizations supporting the zoo, symphony, economic education, healthcare, tourism and inter-faith relationships.