Cairn is a co-founder of FreshTracks Capital and serves as a Managing Director of the Fund. Since 1996 he has owned and operated Cross Vermont Financial, a strategic and financial consultant 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 preparatory 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 also serves on the Steering Committee of the Vermont Investors' Forum, an annual "venture fair" for Vermont companies and is on the board of directors of the Addison County Economic Development Authority. Cairn earned a B.S. (1981) from Montana State University and an MBA (1987) from New Hampshire College. He lives in Hinesburg, Vermont.