He began his education career as a high school social studies teacher in Baton Rouge, Louisiana.

[2] The book was widely cited[3] and well-received, and it earned Hess an early reputation as an astute scholar of education politics and school reform.

[5] Hess drew much attention for the paper, making his controversial case in venues ranging from the White House to the National Press Club.

In an interview with Harvard Ed Magazine, Hess remarked that fallout from his paper was one of the reasons for his eventual departure from the University of Virginia.

[1] In 2002, Hess became the founding director and resident fellow of the education policy studies program at the American Enterprise Institute.

He's also hosted events with keynote speakers across the ideological and political spectrum including Success Academies Charter School Founder Eva Moskowitz; Secretaries of Education Arne Duncan, Betsy DeVos, and Rod Paige; historian and pundit Diane Ravitch; and American Federation of Teachers president Randi Weingarten.

Hess has authored research articles and more general commentaries for scholarly and popular outlets such as Teachers College Record, Harvard Education Review, Phi Delta Kappan, Educational Leadership, U.S. News & World Report, National Affairs, the Washington Post, the New York Times, The Wall Street Journal, The Atlantic, and National Review.

In addition to books and edited volumes, Hess has published a number of scholarly research reports, including School Boards at the Dawn of the 21st Century;[7] A Better Bargain: Overhauling Teacher Collective Bargaining for the 21st Century[8]; Learning to Lead: What Gets Taught in Principal Preparation Programs[9]; Diplomas and Dropouts: Which Colleges Actually Graduate Their Students (and Which Don’t);[10] School Boards Circa 2010: Governance in the Accountability Era[11]; Reauthorization of the Elementary and Secondary Education Act Offers a New Chance to Improve Education[12]; Partnership Is a Two-Way Street: What It Takes for Business to Help Drive School Reform;[13] and multiple entries in lead publications with the U.S. Chamber of Commerce.