Pearson was raised on his family farm in Midland, Virginia. He graduated from Virginia Tech in 1987 with a bachelor’s in agricultural economics.

While at Virginia Tech, Pearson was a member of the Corps of Cadets, earning a commission as a second lieutenant in the Virginia Army National Guard, serving for nine years.  In 1996, he founded Carry-On Trailer, with seven plants in six states and 1,200 employees. Pearson is currently executive chairman of Vehicle Accessory Inc., a leading supplier of vehicle accessories with over 1,000 employees in the United States and Canada. He is a Virginia Tech Foremost Benefactor and a President’s Circle member of the university’s Ut Prosim Society of donors. Pearson also serves on Virginia Tech's Board of Visitors and as a tri-chair of the Boundless Impact Campaign Steering Committee. He is the past chairman of the Corps of Cadets Alumni Board and a former member of the Virginia Tech Foundation Board. Pearson serves as a professor of practice for the College of Agriculture and Life Sciences Department of Agricultural and Applied Economics, where he is also a member of the Advisory Board and earned the Outstanding Alumni Leadership Award. He is married to Renae Pearson ’90 and has two grown children, Anna Kate Bills ’18, a co-chair for the department's Young Alumni Council, and Will Pearson ’20.