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David Ryan

FOUNDER + Managing Partner

David Ryan founded Gray Matters Group in 2002 to address the most pressing issues within the services sector: scalable growth, differentiation, client loyalty, and lack of qualified leads. He knew there was a better way to help services firms accelerate the build out and performance of their revenue generating capabilities.

He leveraged more than twenty-five years of experience across business development, marketing, operations, and executive management to develop Relationship Xpansion (Rx) — one of the industry’s most effective training and coaching programs for billable professionals.

Through Gray Matters, he has worked with some of the world’s most recognizable brands including Deloitte, JLL, Sidley Austin, United Health/Optum, CDW and West Monroe Partners, to name a few. He is a frequent speaker and writer on how professional services companies can enhance the performance of their revenue generation operations resulting in growth, improved profitability, scalability, and increased client loyalty.

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

David received his Bachelor of Science in Business from Miami University and resides in Chicago with his wife and twin daughters.

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Brian Caffarelli


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, providing 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.

Brian 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 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.

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.

We activate service professionals to contribute more to lead generation.

We found Gray Matters Group with one goal: activate professionals to unlock value from their relationships.

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Through GMG’s Rx Program, we empower the other 90%—your front line: billable/non-billable service professionals, to expand their relationships—deepening client loyalty & driving scalable growth for your firm.

We don’t do sales training for biz-dev or services delivery rainmakers.
We focus on your “eyes & ears”, the ones on your front line every day.

We developed Rx,
built from experience,
to change the game for the services sector.

Our facilitators are seasoned business leaders
who bring real world experience.

We've walked in the shoes of our students as billable consultants & subject matters experts.
We’ve “made rain,” selling hundreds-of-millions $ worth of services during our careers.
David Ryan bio photo
David J. Ryan
Brian Caffarelli bio photo
Brian Caffarelli
what we do:
Scalable Revenue Growth
Unlock Differentiation
Fresh Lead-Generation Approaches
3-month impact
new contacts created at current clients
past relationships refreshed
new leads generated
6-month impact
6x ROI
10x ROI
Revenue generated
vs. Rx training $ spent
trusted by

Don’t miss another growth goal.
Schedule a free 30-minute growth assessment today.

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There is a space
between black & white.

It's where consultants
excel & results accelerate—
it’s the ‘gray’ that matters!
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David Ryan,
Gray Matters Group Managing Partner
Learn MORE
David Ryan

Your consultants & their relationships
are an untapped source of value.

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