Jennings has held a wide range of administrative positions in the Stamford Public Schools (Connecticut), including those of assistant principal, principal, administrator for diversity education, equal employment opportunity officer and the district's department head for special education. Prior to going to Stamford, he worked in the Philadelphia School System as a teacher and special education and regular education supervisor.

Jennings, founder of the Dollars for Scholars program in Stamford, which offers scholarships to students who commit to being drug-free throughout their high school years, currently serves on the Nehemiah Commission of Greater Bridgeport, serving the homeless and incarcerated youth of Fairfield County, and has served on the Mayor's Commission for Youth in Stamford.

He has a bachelor's degree in education from Cheyney State University, a master's degree in special education from Antioch Graduate School and an administrative certificate from the University of Pennsylvania.

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