Jennings was introduced to circus while attending Illinois State University, which had a small campus circus troupe. He caught the “circus bug” and, upon graduation, spent the next three years traveling and performing with various small circuses throughout the US. He had a two-year career at Club Med, teaching circus skills and flying trapeze. Jennings joined the staff of Circus Center in 1999. He teaches flying trapeze and trampoline, serves as the company's master rigger, and performs with Xiao Hong Weng a spectacular hand-to-hand balancing act that has won over audiences throughout the Bay Area.