Cheney has spent his career pursuing innovation and entrepreneurship, developing methodologies to design and roll out new products, acquire competitors, and form joint ventures. In 1990 he founded Brand Software, Inc., where he served as its president and chairman of the board and grew the company from a startup to the market leader in behavioral health office management, and by 1999 negotiated its sale to VantageMed, Inc. Immediately prior to SunBug, Cheney worked for groSolar, a Vermont based solar PV and thermal installer and distributor with operations across the U.S. and Canada.