Wobensmith earned a Bachelor of Arts degree in English from the University of Pennsylvania and graduated from the National War College.

[1] Wobensmith served in the United States Navy and worked for five decades in national security under U.S. presidents Richard Nixon, Gerald Ford, Ronald Reagan, George H. W. Bush, and Bill Clinton.

[3] Wobensmith served on the Anne Arundel County Board of Education for nine years[2] and after retirement from federal civilian employment, was vice president for International Marketing for Sensys Technologies in London.

[2][4] Governor-elect Larry Hogan announced the appointment of Wobensmith as secretary of state of Maryland on December 30, 2014.

[5] As secretary of state, Wobensmith oversaw the registration of notaries and charitable organizations and served as the governor's liaison for labor relations.