In 2006, Winfree took a job at The Heritage Foundation, where he researched issues of economic mobility and coauthored a book on that topic published by the Pew Charitable Trusts.

[4] In 2015, Winfree returned to The Heritage Foundation, serving as Director of the Thomas A. Roe Institute for Economic Policy Studies, the Center for Data Analysis, as well as becoming the inaugural Richard F. Aster Fellow.

[7] During the 2016 Presidential transition, Winfree worked alongside Linda M. Springer, a member of the George W. Bush administration,[8] looking forward to achieve a more direct political impact.

"[1] He left the White House and returned to Heritage at the end of 2017, in a move which was anticipated by media and policy experts in Washington,[13] who saw him as well as several other early members of the Trump administration leave after one year in office.

"[18] In 2023, Winfree authored the chapter on the Federal Reserve for the ninth edition of the Heritage Foundation's book Mandate for Leadership, which provides the policy agenda for Project 2025.