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Brian Caffarellli
Affiliated Partner
Brian Caffarelli is an independent consultant and Affiliated Partner with Gray Matters Group. Brian helps his clients develop sales effectiveness strategies, marketing and “go-to-market” initiatives. He works with clients in health care, human resources, and professional services fields. He provides a variety of marketing and sales-related services, including lead generation, marketing communications, sales management, sales training, and sales coaching.
Brian enjoyed a twenty-three year career with Hewitt Associates, one of the world’s largest human resources services firms. He served in several key executive and business development positions.
· He served on Hewitt’s nine-member executive committee for nearly a decade.
· He led Hewitt’s global benefit outsourcing salesforce, developed the company’s sales training curriculum and led
training of more than 500 salespeople and client relationship managers.
· He led the firm’s product development group and managed a global team of 300 product development specialists
and technology professionals that created Hewitt’s market leading benefit outsourcing services.
· He was an instrumental member of the core team that spearheaded Hewitt’s initial public offering in 2004, and he
served as the Chairman of the firm’s Stockholder’s Committee.
Most recently, Brian spent two years with Chicago 2016, working full-time to bring the 2016 Summer Olympic Games to Chicago.
· He was responsible for developing Chicago’s Olympic hospitality brand and for developing Chicago’s Olympic
accommodation strategies and housing programs.
· He spearheaded Chicago’s unique Olympic Fellowship program that provides retired Olympians with four-year
educational fellowships at selected national universities.
Brian is a member of the board of directors of World Chicago and the board of trustees for St. Martin de Porres High School in Waukegan, Illinois. He is an adjunct faculty member of the Lake Forest Graduate School of Management and a frequent guest lecturer at the Northwestern University Center for Leadership and Organizational Change.
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