Jackson is the Oregon Market Leader and Senior Trust Officer for Northwest Trustee & Management Services. Jackson has more than two decades of experience in the fields of estate planning and fiduciary administration. As a "reformed attorney," Jackson was a partner at Portland law firm, Tonkon Torp, leading the firm’s Wealth Planning practice group. He then spent five years as a senior fiduciary executive at Wells Fargo Wealth & Investment Management. Jackson received his BA from Harvard University and his JD from the University of Michigan.

He currently volunteers with the Moot Court program of Civics Learning Project and coaches the Lake Oswego High School team. He previously served on the board of the Oregon Historical Society. Jackson and his wife caravan between Portland and Sunriver with their golden retriever and elderly cat. They have two adult children who will join them occasionally (usually under duress).