Craig Underwood

Passionate promoter of all I believe in. Entrepreneur, CEO, Advisor to Loyalty, Political and Social Entrepreneurs.

Craig Underwood, founder or co-founder of six for-profit and non-profit enterprises, was a pioneer in developing data-based customer loyalty programs and has been an innovator in the social media and nonprofit spaces.  He is an advisor to leading companies, venture capitalists and social entrepreneurs and a political and social justice activist.  He is currently serving as Founding Board Member and Sr. Director of National Accounts for Year Up, the innovative nationwide workforce development program that recruits, trains and places low income inner city young adults in living wage careers with Fortune 500 companies.

Previously, Craig founded The Loyalty Group in Canada, which became one of the largest multi-company customer loyalty programs in the world with 70% of households active members of the program. Started by Craig and two colleagues in a Toronto hotel room, the company now generates over a billion dollars in annual revenue and employs over 2000.  The Loyalty Group is consistently listed as both One of the Best Companies to Work For and One of the Best Companies for Women.  Craig was also a partner at the global strategy consulting firm Bain & Company and Bain’s nonprofit affiliate, The Bridgespan Group.

In addition to his professional career, Craig is an advocate of giving back to the community.  He was a founding board member of Year Up and also a founding board member of Horizons for Homeless Children, a Boston based nonprofit that provides pre-school to the city’s homeless children.  A self-professed “news and political junkie,” Craig served as Alan Khazei’s Policy Director during his 2009 senate race and a founding member of United for Democracy.

A graduate of West Virginia University, Craig served as Student Body President, was named WVU’s 19th Rhode Scholar, and earned a bachelor’s degree in political science in 1980.  He also received a master’s degree in politics, economics and philosophy from Oxford University and a master’s of business administration from the University of Chicago in 1984.

Craig was named Marketer of the Year and has been featured in three HBS Case Studies.  He has published numerous articles on loyalty, entrepreneurial success and leadership and blogs at  Craig’s two teen age children live part time with him in Chestnut Hill, Massachusetts.  He is an active snowboarder, tennis player and cyclist and attends the Bethel AME Church in Jamaica Plain.