 Kittleman was admitted to the Maryland Bar in 1988 and was an associate with Smith, Somerville & Case, 1988–91 (legal assistant, 1984–88) and a partner with Herwig & Humphreys, LLP from 1996 to 2003 (associate, 1991–96).Kittleman has worked for the law firm Godwin, Erlandson, MacLaughlin, Vernon & Daney since 2008, though is not listed currently among the firm's attorneys.He is the son of the late Robert H. Kittleman and was appointed by Governor Bob Ehrlich (R) to fill his seat in the Maryland Senate.