For its first 16 years, The Cypress Group worked with multi-billion dollar Silicon Valley venture capital firms, building executive teams for early-, mid- and late-stage startups. After purchasing a second home in St. Helena, co-founders Jim Anderson and Courtney Andrain fell in love with wine country and moved to St. Helena full time. Recognizing that the wine industry was becoming more complex and competitive, they saw the need within the rapidly growing wine industry for the type of high-level executive search expertise. The Cypress Group had been providing high-technology clients.