After receiving his Juris Doctor from the University of Colorado School of Law, Lief served as a managing partner of a Colorado law firm, Roper, Lief, Mains and Cobb, from 1977-83. He was the first president of the Yonkers, New York–based Greyston Foundation, one of the earliest and best-known models of integrated nonprofit social enterprises and service providers in the country. Under his leadership Greyston Foundation grew from a startup with a handful of employees to an organization with 180 employees and a $20 million annual budget. Greyston’s mix of services includes permanent housing for formerly homeless families, accredited childcare, HIV/AIDS housing and health care and the well-known Greyston Bakery, which provides employment to low income residents of Yonkers and among many other products, supplies millions of pounds of brownies to Ben and Jerry’s.
A principal in the Hartland Group, Community Developers and Consultants of Burlington, Vermont, he has been instrumental in the creation of mixed income housing and economic development projects in Vermont and New Hampshire. He has also served as the strategic planning consultant to Amida Care, a highly regarded nonprofit Special Needs HMO serving 5,000 low-income persons living with HIV/AIDS in New York City. For decades Chuck has served on nonprofit boards in New York, Vermont, Nova Scotia and nationally. This board work includes service as chair of the Intervale Center in Burlington which develops farm-and land-based enterprises generating economic and social opportunity while protecting natural resources, vice-chair of the board of the Vermont Community Loan Fund, and member of the Center for Cartoon Studies and Vermont Works for Women boards. He was the chair of the national Social Enterprise Alliance, as well as as board member and past chair of Shambhala International.
He and his wife, Judith, herself a distinguished former Naropa president and board member, have two daughters, both Naropa University graduates, and three grandchildren.