Robert L. Cherry

Chief Executive Officer

As a trusted workforce development and public policy executive with extensive experience providing professional leadership and direction, Robert Cherry is committed to a thriving workforce. He is an active champion for businesses and job seekers, implementing programs, policy initiatives, and community engagement.  

Since April 2020, Robert has managed six bureaus that include the Division of Administration, Division of Vocational Rehabilitation, Department of Unemployment Insurance, Division of Employment and Training, Division of Equal Rights, and Division of Workers Compensation as the Appointed Deputy Secretary of the Wisconsin Department of Workforce Development (DWD). Over the last 15 months, Robert has led 2,500 employees and partnered with the Wisconsin Department of Veterans Affairs, Wisconsin Department of Disabled American Veterans, Wisconsin Economic Development Corporation, and the Veterans Chamber of Commerce for a Vets Ready initiative, an employer recognition program highlighting employers committed to the veteran workforce. He also spearheaded a complex program that provided additional unemployment insurance dollars into the hands of out-of-work Wisconsinites.

Before DWD, Robert spent five years at Employ Milwaukee, the workforce development board serving Milwaukee County, in multiple roles, including Vice President of Planning and Development, Chief Development and Partnership Officer, and Director of Career Exploration. He is most proud of developing and implementing the Career Plus program that consisted of year-round combined workforce training, subsidized improvement, and social-emotional development delivered to City of Milwaukee citizens ages 15-24. Robert spent his early career at the Community Advocates Public Policy Institute and the Center for Urban Population Health. 

In July 2021, Robert will be assuming the role of Chief Executive Officer at Partner4Work, the leader of the public workforce system for Pittsburgh and Allegheny County. As CEO, he will continue Partner4Work’s strong momentum to drive workforce development activities, a vital component of the region’s overall economic vitality. Robert will build successful partnerships, innovate new ideas, and pilot strategic solutions that will continue growth and connect the workforce with the jobs of today and in the future.

Robert received a Bachelor of Science in Criminal Justice at the University of Wisconsin-Milwaukee. He is an elected Board Trustee of the Village of Brown Deer and is responsible for developing and approving its mission, strategic goals and establishing policies related to programs and services.