[2] He graduated from Walter E. Stebbins High School in 1989,[3] and from Dartmouth College in 1993 with an A.B., magna cum laude, in History.
After college, Engstrom joined the Mississippi Teacher Corps and taught high school English and coached football.
[8][9] In 2020, Engstrom was a principal adviser to the Administrative Conference of the United States and co-author of a major report with Mariano-Florentino Cuellar, Daniel Ho, and Catherine Sharkey on the use of artificial intelligence by federal agencies.
[18] Engstrom has published legal commentaries in the New York Times,[19] Slate,[20] Bloomberg,[21] and CNN.
[22] His history of a novel lawsuit against General Motors for sex discrimination in the 1930s was featured in Smithsonian Magazine in 2022.