Heisman is well known throughout the Philadelphia chess scene. His chess activities include promoting local chess, hosting a chess radio show "Ask the Renaissance Man" on ICC Webcast, and organizing events like the Philadelphia Championship and Philadelphia Junior Championship. He is currently a member of the Main Line Chess Club and the SE Scholastic Coordinator for the Pennsylvania State Chess Federation. He maintains an extensive web page which provides information on Philadelphia area chess and many articles on chess improvement. Heisman is a chess tutor and has taught radio DJ Howard Stern. He helped mentor the 2007-08 National High School champion Dan Yeager, who attended his old high school (Hatboro-Horsham High School).