[8] After graduating from Harvard, Stearns worked for the baseball operations departments for the New York Mets and the Arizona Fall League.
"[13] At that time, the Milwaukee Brewers began searching for a new general manager, prioritizing youth and experience with data analytics, which the Astros used in their rebuild.
[13] On September 21, 2015, the Milwaukee Brewers named Stearns their next general manager, succeeding the retiring Doug Melvin, who they announced would remain with the team in an advisory role.
[20] His first transactions included trading Jonathan Lucroy and acquiring Travis Shaw, Eric Thames, and Anthony Swarzak.
[21] In 2018, Stearns signed free agents Lorenzo Cain and Jhoulys Chacin, and executed the trade for Christian Yelich, who won the National League MVP in his first season as a Brewer.
The Brewers were in second place in the NL Central by the MLB trade deadline, and he orchestrated moves to acquire Mike Moustakas, Curtis Granderson, Gio Gonzalez, and Jonathan Schoop.
[citation needed] In January 2019, the Brewers signed Stearns to a contract extension and promoted him to president of baseball operations and general manager.
"[26] Stearns is generally considered to have presided over the most successful stretch in Brewers history, guiding the organization to four consecutive playoff appearances from 2018–2021, and earned the reputation as one of the most respected executives in MLB.
[28] Stearns planned for the 2024 season to simply be a transitional one for the Mets, however, despite a 24-35 start, the team significantly improved, with Stearns receiving a lot of credit, including endorsing Mark Vientos as the starting 3rd baseman, who finished with 27 home runs and 71 RBIs, and promoting Jose Iglesias to the majors, who achieved a .337 batting average.