Executive Leadership and Affiliates

Gray Matters’ facilitators and consultants are seasoned business leaders who bring real world experiences, AND TWO ESSENTIAL characteristics to our training and coaching engagements.

They have:

  1. Walked in the shoes of our students as billable consultants and subject matters experts – having navigated tough client situations, produced robust deliverables, met tight deadlines and aggressive utilization targets.
  2. “Made rain”– having sold millions of dollars worth of services during their careers.


With an average of over 20 years of experience, the Gray Matters’ team is able to quickly understand the business landscape, drivers, firm practices, hot buttons, and vernacular of our clients.


David J. Ryan

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Managing Partner – Gray Matters Group

Mr. Ryan has over twenty five years of experience across business development, marketing, operations, and executive management. He has worked with leading companies including Deloitte, JLL, Sidley Austin, United Health/Optum, CDW and West Monroe Partners. He is a frequent speaker and writer on how professional services companies can enhance the performance of their client development operations resulting in revenue growth, improved profitability, scalability, and increased client loyalty.

After completing his MBA at Northwestern University’s Kellogg Graduate School of Management, Mr. Ryan began his career with IBM where he excelled in numerous sales, marketing, and operations positions.  Following his days with IBM, Mr. Ryan worked extensively in the professional services sector in both execution and leadership capacities across consulting, operations, and business development.

Prior to starting Gray Matters Group, Mr. Ryan spent seven years as an Executive Committee member and SVP at The Revere Group, a leading technology and business consulting firm. He was responsible for the build out of Revere’s overall “go-to-market” strategy and processes.

Mr. Ryan has traveled extensively with stints in Europe, Australia, New Zealand and Southeast Asia. In addition, Mr. Ryan holds board and advisory positions with The Cara Program and Old St. Patrick’s Church.

Prior to his Kellogg MBA, Mr. Ryan received his Bachelor of Science in Business from Miami University. He resides in Chicago with his wife and twin daughters.

Brian Caffarelli

Brian Caffarelli Headshot

Affiliated Partner – Gray Matters Group

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 sales force, 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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