For 15 years, Skip served as director of community relations and public affairs at The Boston Globe newspaper, where he championed high-quality public outreach between the newspaper and ethnic associations, non-profit organizations, special interest advocacy groups and small town and county governments. Skip was one of a nine-member consortium team representing The Boston Globe, Fleet Bank, and the Massachusetts Institute of Technology to successfully organize a major conference on the future of development in the waterfront area. He has also organized other major conferences, including one on health care for 400 top-level executives, which included the U.S. First Lady, seven senior United States Senators, top health officials, and economists as presenters. As an executive on the Board of Directors of The Boston Globe Foundation, he awarded grants totaling 2.5 to 4 million dollars annually. As Associate Dean of Student Affairs and Director of the African American Institute at Northeastern University in Boston, he managed a staff of 12 professionals, 20 part-time tutors, and 4 interns.
Skip has a significant background in civil rights, community organizing, and community education initiatives, and was a plaintiff in a landmark school desegregation case during the Civil Rights era, Griffin vs. Prince Edward County, Virginia. He served as a strategist and media relations advisor for the Ten Point Coalition. He holds a B.A. in Government from Harvard College and a Masters of Education in Organizational and Social Policy from the Harvard Graduate School of Education.