Chessa is Director of Career Services for Work Opportunities’ Annapolis market, serving the Annapolis, Linthicum, and Columbia region. Formerly known as Maryland Central, the market was divided into two new offices, Annapolis and Baltimore, in July of 2018 to meet the increased demand for the organization’s services. As Director, Chessa oversees her team to ensure they are carrying out WOU’s mission of providing job development, placement, and training services to students and adults with disabilities and other barriers to employment through referrals from state, local, and private sources.

Before joining Work Opportunities in October of 2017, Chessa spent 10 years with the YMCA, serving in various leadership roles in Rhode Island and Maryland. Most recently, she was Operations Director, responsible for hiring and managing a staff of 120 to serve more than 300 campers each summer season.

Chessa graduated from the University of Maryland University College with a bachelor’s degree in arts and humanities. When she isn’t exploring different parts of the world in her free time, Chessa’s life revolves around doting on her two dogs and spending time with family.