At the onset of his career, Cobb began as an auditor in the inheritance tax division of the Tennessee Department of Revenue. Subsequently, he transitioned to the legal field, commencing his legal practice under the guidance of Charles Perkins for a year, followed by a year-long stint as an assistant city attorney. Later, he became a member of the law firm Neely, Green, Fargarson, and Brooke, dedicating 15 years of service there. Before his appointment as a judge, he spent a year practicing law from his home. Throughout his 18-year tenure as a lawyer, his area of expertise focused on insurance litigation. In 1994, he joined the Shelby County Attorney's Office, working part-time until assuming his role as a judge in 1997.