Sky began his career in 1983 with the Bank of Boston in its High Technology Division, making equity-oriented loans and direct equity investments in early-stage high tech companies. In 1989, he joined the investment staff of Pacific Life Insurance Company and made direct investments in private debt and equity, as well as in investment limited partnerships (LBO, Mezzanine and Venture funds), both on a primary and secondary basis. In 1990, Sky co-founded the private equity firm today known as Windjammer Capital Investors with over $2 billion under management.
In 2007, Sky founded SustainVC and since then has devoted his time entirely to investing for-profit dollars into early-stage companies that are making a positive difference in the world.
Sky’s non-work passion is singing bass with his 8-person a cappella group called “The Works!”