Weiss has served as co-chair of the Russia Studies Centre at the Henry Jackson Society (HJS).
Weiss currently serves as the editor-in-chief for the online magazine Interpreter, which translates and analyzes Russian news, and senior editor of The Daily Beast, a regular columnist for Foreign Policy magazine. In 2015, he co-wrote the book ISIS: Inside the Army of Terror with Hassan Hassan.
In November 2014, Weiss published an a special report in his online magazine the Interpreter that accused Russia of waging “propaganda and disinformation” campaigns. Weiss’s report included recommendations on how to confront Russian propaganda which included creating an “internationally recognized ratings system for disinformation.” The recommendations were criticized in The Nation by James Carden of the American Committee for East-West Accord as a “censorship campaign.”