Daniel P. DiCaro

Operating Director
(312) 494-9800

Dan has extensive business experience as an executive in several public and private companies. With those companies, he has been responsible in various roles for all aspects of executive level management including areas such as product and business development, finance, operations and general management and has a strong background in corporate finance, mergers and acquisitions, private equity and venture capital financing

Dan was a co-founder of PRIMIS Marketing Group, Inc. which was formed to create a leading integrated provider of marketing solutions to middle market companies by executing a “buy and build” strategy.  With Dan as CFO and COO, PRIMIS successfully completed a series of acquisitions and grew organically into a leading marketing services company that was acquired by Parthenon Capital in 2006.

Previously, Dan was a Co-Founder and Managing Director of Gray Drake Partners, which provided strategic business and financial advisory services to technology and IT service-based businesses. Representative client engagements included: advising CEO and COO of a $300 million multinational public software and information service company seeking to recapitalize, restructure and launch new business; ongoing advisor to several private venture capital backed software and service companies; and serving as interim President and executing a sale of a marketing services firm that was a portfolio company of a major private equity fund.

He has also served as CFO/COO of several public and private-equity backed software and information services companies, serving a variety of industries including embedded systems, healthcare, entertainment and the insurance industry.  Each of these businesses was acquired in successful mergers or outright sales.

He currently has extensive Board experience, having served on the Board of Directors of Northwest Community Healthcare from 2001-2013 (including serving as Chairman of the Board of Directors of Northwest Community Healthcare from 2008-2011). He has also served on the Boards of PRIMIS Marketing Group, CPRi, Inc, Information Kinetics, Inc, Imagination Pilots Entertainment and Generator Corporation. He was selected and served as a member of the DePaul University Finance Advisory Board, and is the past Chairman of the Chicago Software Association Early Stage Investment Conference.


  • PRIMIS Marketing Group, Inc.
  • Gray Drake Partners
  • Software Development Systems
  • Medicus Systems Corporation
  • Imagination Pilots Entertainment
  • CCC Information Services, Inc.
  • Ernst & Young


  • DePaul University B.S. Accounting
  • CPA State of Illinois
  • MBA, Kellstadt Graduate School of Business, DePaul University