McCaffrey earned a BA in experimental psychology from the University of California, Irvine, a B.A.
[1] Prior to joining Microsoft, McCaffrey was the Associate Vice President of Research at Volt Information Sciences in Redmond, Washington, supporting the needs of software engineers at Microsoft.
[citation needed] He then became a research software engineer at Microsoft Research, where he directs the internal Microsoft AI School, focusing on creating machine learning and artificial intelligence algorithms.
He is the Senior Technical Editor for Microsoft's Visual Studio Magazine.
His other research interests include combinatorics, especially when applied to human behavior such as sports betting and Blackjack Switch, as well as "software systems which have designs influenced by the behavior of biological systems such as swarm intelligence optimization and simulated bee colony algorithms and their application to data mining.