[3] After graduation, Ashford moved to New York City, where he shared an apartment with friend and fellow choreographer Kathleen Marshall.

[15] He directed and choreographed Promises, Promises starring Sean Hayes and Kristin Chenoweth in 2010 (Tony Nomination for Best Choreography)[16] and How to Succeed in Business Without Really Trying starring Daniel Radcliffe and John Laroquette in 2011,[17] receiving Tony Nominations for Best Direction of a Musical and Best Choreography of a Musical.

staged concert series, Ashford has choreographed:[20] Tenderloin (2000), Bloomer Girl (2001),[21] A Connecticut Yankee (2001),[22] and Pardon My English (2004).

[24] In April 2015, Ashford directed and choreographed an acclaimed production of Carousel for the Lyric Opera of Chicago, starring Laura Osnes and Steven Pasquale.

[26] Off-Broadway credits include Pardon My English (2004), The Thing About Men (2003), Bloomer Girl (2001), A Connecticut Yankee (2001), and Time and Again (2001).

[31] Ashford co-directed, with Jason Moore, the West End production of Shrek The Musical, which ran from 2011 to 2013 at the Theatre Royal Drury Lane.

Royal National Theatre choreography credits include A Funny Thing Happened on the Way to the Forum (2004)[39] and Once in a Lifetime in 2005.

[47] For television, Ashford has choreographed tributes to Andrew Lloyd Webber, Barbra Streisand, Jerry Hermann, Meryl Streep, Barbara Cook, Shirley MacLaine, and Tom Hanks for The Kennedy Center Honors.

[62] In February 2019, it was announced that Ashford would direct a film adaptation of Andrew Lloyd Webber's stage musical Sunset Boulevard, starring Glenn Close reprising her on-stage role as Norma Desmond.