Our Team

Randy Coppersmith


Randy Coppersmith is Chairman of Cortland Advisors. He joined the firm in October 2017. During his career he has been involved in over 57 M&A transactions. His expertise in corporate operations, finance, capital restructuring, divestitures, M&A, sales and marketing have supported clients around the world for over 40 years. He is often brought in to help prepare companies for a material event.

He is also the chairman of The Hollymar Group, a private family investment office. From 2002-2016 he served as Chairman and CEO of Intercom Consulting & Federal Systems, a government contracting company with deep Networking and Cyber Security capabilities. Intercom was acquired in a highly successful exit in August 2016 by Belcan Corp. Previously he was managing partner of New Road Partners, LLC, a Virginia-based investment banking boutique, where he also ran a successful venture fund unit.

Prior to this, Randy was Vice President of Marketing Communications for AOL Studios, a division of America Online, Inc., and served as an AOL Corporate Officer. At AOL he led a team responsible for acquiring, creating and marketing original content offerings.  He is also credited with having sold the first commercial ad on AOL, to Starbucks, in 1996. Before joining AOL, he was a Senior Partner and Vice President of Redgate Communications in San Francisco. Redgate, the first new media agency, was Ted Leonsis’s company that was successfully acquired by AOL.

In his prior roles Randy was Executive Director of Corporate Communications for Intergraph Corporation in Huntsville, Alabama. Earlier, he held senior communications positions with Edelman Public Relations and IBM corporate affairs. From 1976-1982 he was a journalist, where he worked for The Tampa Tribune, The Springfield (MO) Daily News, The Fort Lauderdale Sun-Sentinel and the Associated Press.

He has a BA in Journalism from  the University of South Florida and has an MBA from the Yale School of Management. He has also completed graduate work at the University of Alabama; and the University of Hawaii’s Japan-America Institute.  He serves on a number of corporate and non-profit boards including: The Hollymar Group, The Sigma Chi Foundation’s Board of Governors, The Theta Beta Scholarship Fund and Words-Matter.net. He is a frequent guest lecturer at colleges and universities.