Cross is a co-founder of FreshTracks Capital and serves as a Managing Director of the Fund. From 1996 to 2000 he owned and operated Cross Vermont Financial, a strategic and financial consultancy to Vermont banks and growth businesses such as Collector Online, Otter Creek Industries, Green Mountain Coffee Roasters, and the Merchants Bank. Cairn served as the CFO of Otter Creek Industries to restructure its operations prior to achieving a profitable sale of the company.

From 1996 to 1998, Cairn was the Assistant General Manager of Green Mountain Capital, L.P. From 1991 to 1996 he was a Vice President and Corporate Loan Officer for the Howard Bank, preceded by five years service in various positions for Vermont National Bank including Commercial Loan Officer. Cairn co-founded a small specialty food manufacturer in Vermont and has been an investor in and a Member Manager of Snow Farm Vineyard, LLC, Vermont's first grape wine producer located on Grand Isle.

Cairn formerly served as Co-Chair and Steering Committee member of the Vermont Investors' Forum, an annual "venture fair" for Vermont companies, and previously served on the board of directors of the Addison County Economic Development Corporation. In 2002, he was appointed by Governor Howard Dean to the Vermont State Board of Public Accountancy and to the Workforce Recruitment Board. He was reappointed to the Workforce Recruitment Board by Governor James Douglas in 2005. Also in 2005, Cairn was appointed by Speaker of the Vermont House, Gaye Symington to her business advisory committee.

Cross serves on the boards of numerous FreshTracks portfolio companies.  Cairn is currently the Chair of the Board for the EatingWell Media Group, and is a member of the Board of Directors at both Vermont Teddy Bear,  and NativeEnergy.  Prior to the sale of M2S, Cross was an observer to the company's Board of Directors, and a member of the board's ad hoc audit committee.  Prior to the sale of ISIS, Cross was also an observer to that company's Board of Directors.  

Cairn earned a B.S. (1981) from Montana State University and an MBA (1987) from New Hampshire College (now Southern New Hampshire University).  He lives in Ferrisburg, Vermont.