Buckley is the son of Barbara J. (King) and Andrew P. Buckley.[1] He has two brothers and a sister. He attended Pine Crest School, where he graduated in 1983, and Stanford University, where he graduated in 1987 with a bachelor's degree in political science.[4] He played golf on the Stanford Men's Golf Team. He later studied sketch comedy and improvisation at the Groundlings Theatre, working with comedians Melissa McCarthy and Dax Shepard.[5] Prior to breaking through on The Office he worked as a financial advisor at Merrill Lynch for 5 years and he continued working there for another 6 years afterwards.[6]
Buckley played David Wallace, embattled CFO and later CEO of the fictional Dunder Mifflin Paper Company, in 37 episodes of The Office from 2006 to 2013. At the time of his initial appearance, he had been working as a financial advisor at Merrill Lynch, and had been cast specifically because of his familiarity with the world of corporate finance. He continued to work in the finance industry full-time during his recurring role on The Office.[7]
In 2018 Buckley appeared with golfer Phil Mickelson in a commercial for Workday, Inc with Mickelson acting as his "Business Caddy" for important business decisions.[11]
In 2020, Variety announced Buckley was joining the cast of the Chris Blake quarantine comedy, Distancing Socially. It would mark Buckley's second on-screen collaboration with the director. The film was shot at the height of the COVID-19 pandemic in 2020, using remote technologies and the iPhone 11. The film was acquired and released by Cinedigm in October 2021.[12]