While in the Air Force, he was trained as a clerk but was later cross-trained as a public information specialist ending his military career in the fall of 1959.
In 1978 Dockery organized Summit’s first self-insurers fund, Associated Industries of Florida, which commenced operations April 1.
Later that year, the Florida Retail Federation engaged Summit to start a self-insurers fund for workers’ compensation commencing business January 1, 1979.
Additional self-insurers funds for workers’ compensation were formed by Summit in Louisiana, Georgia, Missouri, and Oklahoma.
[5] Shortly thereafter Dockery was invited to become member of the board of directors of Summit Holdings, helping take the company public in 1997.
[7] After the election of Governor Bob Martinez in 1986, Dockery was appointed to the Florida High Speed Rail Commission, serving as chairman before the effort was abandoned.
[10] Dockery has remained an enthusiastic supporter of high-speed rail, which surfaced again when President Barack Obama was elected in 2008 and pledged more than $2 billion for the construction and operation of the Tampa/Orlando link.