Gary Schiff, a native of Adams, Mass., has deep roots in the Berkshires, with his family history in the region dating back to 1896. From 2015 to 2025, he served as the managing director of October Mountain Financial Advisors, a division of St. Germain Investment Management and a joint venture with Lee Bank. His career spans more than two decades in wealth management, including leadership positions at TD Private Client Wealth LLC and TD Bank USA’s predecessor banks. Before that, he held roles with MASS MoCA, Heritage Development Group, and the SWA Group. A committed community leader since the 1980s, Gary serves on the board of CATA, the Berkshire Funders’ Roundtable, and the Massachusetts College of Liberal Arts Foundation, among many others. He has also been involved with economic development and arts organizations across the county. A graduate of Middlebury College with an M.A. from Harvard University, Gary also holds FINRA Series 7 and 63 licenses and is certified as an Alpine Level 3 ski instructor. Gary resides in Lenox, Mass.
