Clare O'Connor, currently serving as the Director of Workforce Development, has done national and grassroots work focusing on employment and youth related issues from a broad community perspective. She joins the Chamber after being at Cape Cod Community College as the manager of the Cape Cod, Martha's Vineyard, and Nantucket School to Careers partnership among businesses and educators. This partnership drew over $1.2 million in new funds for the region, and established pilot programs placing youth in internships and learning experiences at local businesses. Coming to the Cape in 1993, her early work at Jobs for the Future in Boston, established a National Health Employer network. Working as a private consultant, she has provided technical assistance to Hopkins Hospital and the 15 other hospitals in the Youth Mentoring Network as they developed their career guide models. Her expertise in collaborative efforts was also used by the One to One Mentoring Partnership, Inc., to restructure their cornerstone effort in New York City.

Before moving to Cape Cod, Clare worked as a legislative aide in the U.S. Senate and then spent most of her career in New York City. There, she established the Senior Employment Service for people over 55, conducted public policy research, and left the City as the Director of External Programs for the New York City Public School system, responsible for all school/business partnerships. On her departure, she received a Mayoral citation for her innovative approaches in helping New York City's children.