Drew graduated in 1991 from the University of Kentucky with a degree in Landscape Architecture.

After graduation, he worked on the maintenance crew at his home course for one year, Drew took on a full-time position with the design staff for world-renowned golf course architect, Arthur Hills. As the firm continued to grow, so did the opportunities for Drew. He quickly took on full management of multiple new course and renovation projects and became a recognizable face for the firm. During Drew's years with Arthur Hills/Steve Forrest & Associates (AHSF), Drew collaborated with Arthur on over 30 full 18-hole designs and over 20 major renovations.

In 2010, Drew established his own design practice.