From 1995 to 1999, he was Director of Speechwriting, serving as Assistant to the President, and was responsible for writing or editing nearly 2,000 speeches, including four State of the Union and two Inaugural Addresses.

[2] Prior to his government service, Waldman was the executive director of Public Citizen's Congress Watch, then the capital's largest consumer lobbying office (1989–92).

[7] On April 9, 2021, Waldman was named to the Presidential Commission on the Supreme Court of the United States by President Joe Biden.

Appearances include Good Morning America; PBS Newshour, CBS Evening News; the O'Reilly Factor; Nightline; 60 Minutes; Hardball with Chris Matthews; CNN's Crossfire; the Dylan Ratigan Show; color commentary on NBC (State of the Union) and ABC (Obama inaugural); NPR's Morning Edition; All Things Considered; Fresh Air; Diane Rehm; The Colbert Report; and many other programs.

His brother, Steven Waldman, co-founded Beliefnet and formerly served as a senior advisor to the chairman of the Federal Communications Commission.