Kenneth Haley has practiced law since early 2000. He received his juris doctor from the John Marshall Law School in Chicago, Illinois, through which he completed a clerkship with the City of Chicago's municipal prosecutions department. After graduation, Kenneth Haley accepted a position with the city as assistant corporation counsel for individual defense litigation, in which role he defended leaders and officers of the Chicago Police Department.

Kenneth Haley then went on to become a legal specialist with the District of Columbia Superior Court in Washington, DC, where he provided case and judicial support in matters pertaining to child neglect and abuse. He remained in this position for just over two years, after which time he transitioned into a contract specialist role with the General Services Administration. Responsible for award planning and negotiations, as well as invoicing and payment, he advised on appropriate contract types and case-specific provisions.

Subsequently named to the General Services Administration's employment and labor law department, Kenneth Haley focused on employment discrimination and employee relations. After three years, he went into the private sector as a legal advisor and human resources consultant to TransUnion Settlement Solutions, where he oversaw the development and implementation of human resource policy. Four years later, he launched his own private practice, the Haley Law Group, where he focuses on criminal law.