Prior to 424 Capital, Jackson was a Financial Services Representative with Baystate Financial where he was responsible for supporting high-net-worth clients with structural financial planning and utilizing diverse asset allocation strategies and customized portfolio designs based on investment goals, saving patterns, and risk tolerance. Prior to Baystate Financial, Jackson served in the United States Air Force as an Air Traffic Controller. He continues to serve as a member of the New Hampshire Air National Guard.

Jackson earned his M.B.A from Boston College and his B.S in Business Management from The University Of New Hampshire.