Jackson hit .083 (1-12) and scored four runs in 28 games for Linfield in 2014 as a backup outfielder. In 2013 he hit .154 (2-13) with no homers or RBIs in 27 games for Linfield's NCAA Division III national-championship team. He played primarily as a pinch runner or late-inning defensive replacement, scored five times and was 3-for-3 in stolen bases.

He lettered six times in football and baseball at West Albany High School in Oregon, was a three-time Mid-Willamette Conference all-star and was a two-time 5A all-state selection. He hit .421 for his career at WAHS.