Randy WaterfieldJ. Randall Waterfield is Chairman of The Board & Chief Executive Officer of Waterfield Holdings. Waterfield traces its roots back to 1928, when Richard H. Waterfield founded Waterfield Mortgage Company and Waterfield Insurance Agency in Fort Wayne, Indiana. After selling the largest private mortgage company in the US and largest Indiana based bank in 2006 and 2007 respectively, Waterfield has diversified into technology, real estate, asset management and merchant banking. Waterfield today has over $2 billion in managed assets.

Mr. Waterfield was the 2017-2018 Chairman of Young Presidents Organization (YPO) International (www.ypo.org), an organization of over 30,000 CEOs from over 140 countries with combined revenue of over US$ 9 Trillion. He is also a director of SMTC Corporation (NASDAQ: SMTX), Red Oak Partners, WTI Holdings, and former Chairman of YPO New York City, among other board positions further detailed below. Prior to joining Waterfield, Mr. Waterfield was employed by Goldman Sachs Asset Management, where he was responsible for the small cap growth portfolios. Prior to his employment with Goldman, Sachs, & Co., Mr. Waterfield trained at Fidelity Investments in Boston, and Prudential Securities in New York. Mr. Waterfield graduated from Harvard University in 1996; he holds the Chartered Financial Analyst designation (CFA) and is a member of MENSA.


Mr. Waterfield is currently, or was previously, a member of the following boards of directors:

  • Waterfield Group
  • Waterfield Enterprises
  • Waterfield Asset Management
  • Waterfield Private Equity Fund(s) I,II, & III
  • Waterfield Technologies
  • Waterfield Energy
  • Affinity Financial Corporation
  • National InterBank
  • Waterfield Financial Services
  • Young Presidents Organization New York City
  • Asure Software (NASDAQ)
  • Culver Military Summer Academy
  • TheRateReport
  • Cappello, Waterfield & Co.
  • Fife, Waterfield & Co.


Through the Waterfield Foundation, Mr. Waterfield supports a variety of environmental and Midwestern based causes.


Mr. Waterfield has been a frequent guest on CNBC, MSNBC, Fox News, and CNN Radio. He has been quoted in numerous publications, including the Wall Street Journal, The Los Angeles Times, The San Francisco Examiner, The Orange County Register, and American Banker, among others.


Mr. Waterfield graduated from Harvard University in 1996. He is a member of MENSA and holds the Chartered Financial Analyst designation (CFA).