For 50 years Will has labored in the field of small business. Returning to his native Vermont after college and travels, Will started and operated several small businesses in Rutland County, one of which was Ben & Jerry's franchise #12 which led to a career with Ben & Jerry's Homemade Inc. He retired in 2007 as Director of Retail Operations with responsibility for 600 scoop shops in 14 countries. Retirement was short-lived however when he was hired as Executive Director of Vermont Businesses for Social Responsibility. In the fall of 2010, Will retired again to sail with his wife, Kathleen, to the Bahamas. In 2012 Will and Kathleen opened the Hinesburgh Public House, a Vermont Benefit Corporation, to fill a need for a gathering place in town.
Will serves on the board of the Lake Champlain Sailing Center and the advisory boards of Main Street Alliance and Let's Grow Kids. He is also a member of the Vermont Economic Development Authority.