Heckenkemper was born in Tulsa, Oklahoma and graduated from Oklahoma State University with a Bachelor of Science degree in landscape design. Heckenkemper began his career in the 1980s working for Poe and Associates. Later he worked as the senior land planner as the company entered into a partnership with Jack Nicklaus and Associates.
In 1983, Heckenkemper joined the partnership of Tom Weiskopf and Jay Morrish, where he oversaw the construction of several high-profile golf courses. In 1985 he founded his own company, Heckenkemper Golf Course Design.