Heisman authors the award-winning Novice Nook columnist, aimed at improving adults, for the popular Chess Cafe Web site. He has also written eight books on chess, including Elements of Positional Chess Evaluation, Everyone's 2nd Chess Book, and Looking for Trouble.

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 among his current students is radio DJ Howard Stern.

Heisman began his career as an engineer and worked in that capacity with several organizations, including the Naval Air Development Center and Intermetrics, Inc. Later, Heisman became a Registered Investment Adviser in Pennsylvania; he has been a full-time chess instructor and author since 1996. He is also a member of the Society for American Baseball Research and had a baseball newsletter, "Baseball's Active Leaders". His hobbies include backgammon, science fiction, collecting comic books, and following the Philadelphia sports teams. He helped mentor the 2007-08 National High School champion Dan Yeager, also from Hatboro-Horsham High School.

Heisman graduated from Hatboro-Horsham High School in Pennsylvania as the co-valedictorian in 1968, and was elected to the school's Hall of Fame in 2007. He attended Caltech and transferred to Penn State in 1969. In 1971 Heisman graduated at the top of his class earning a B.S. in Mathematics, and in 1983, again at the top of his class with a 4.0 G.P.A., received his Masters Degree in Engineering, both from The Pennsylvania State University.