Kevin Wolff was born and raised in San Antonio. He graduated from Clark High School and joined the U.S. Navy immediately following high school graduation. Wolff was responsible for communications on board the U.S.S. Mahan DDG-42, a guided missile destroyer. When his ship crossed Qaddafi's "Line of Death" in the Gulf of Sidra, Wolff was awarded the Navy Expeditionary Medal for armed conflict against an enemy. After serving four years of active duty, he remained in the reserves for four more years while earning his B.B.A. and M.B.A. from St. Mary's University.

Wolff's employment in San Antonio includes Human Resource Manager for Fiesta Texas, and Senior Recruiter, Human Resources Generalist, and Operations Manager for Citigroup. The Wolff family relocated to Delaware where Kevin held positions involving Business Development and as Human Resources Director before he was transferred to New York City, where he served as the Regional Human Resources Director.

Wolff returned to San Antonio as Executive Vice President and Chief Operations Officer for First American Title Insurance Company in San Antonio. In May, 2005 Kevin was elected to the San Antonio City Council.  He served as the District 9 representative until January, 2008 and was elected to Bexar County Commissioners Court Precinct 3 in November, 2008.