Roland was born in Bozeman, and raised in and around Great Falls, Montana. After graduating as class valedictorian from Great Falls High, in 1988, he attended the University of Montana on a Presidential Scholarship. He graduated from the University with high honors, earning a degree in economics, in 1991. He then went on to law school at the University of Montana, during which time he both worked in a large law firm, and as an intern in the USDA legal department. Following his graduation in 1994, he returned to Great Falls to start a private practice. He joined the present firm in 1996. Roland is a successful trial attorney, active member of the legal and civic communities, and recipient of the Robert P. Goff pro bono award. He has a wife and three daughters. Both he and his wife are pilots. The whole family enjoys outdoor pursuits.