Randall Greenwood graduated from Oak Hill High School and earned a Bachelor of Science in Business Management from the University of Southern Maine. He has a background in small business management, having owned Mixers Nightclub & Lounge and managed other local establishments. Greenwood has served multiple non-consecutive terms in the Maine House of Representatives, representing both the 82nd and 56th districts. He currently holds positions on the town of Wales Board of Selectmen and as the town's general assistance administrator. Greenwood is actively involved in local community organizations, including serving as Treasurer for the Pleasant Hill Cemetery Association and participating in the Sabattus Recreation Club.

Randall Greenwood's political identity is shaped by his deep-rooted commitment to local governance and small business advocacy, which often leads to unexpected alliances. His legislative record reveals a calculated approach to balancing regional industrial interests with environmental regulations, hinting at an ideologically agile strategy. Greenwood’s background in running a nightclub and managing a small business informs his economic policies, which prioritize local control over centralized mandates. His rhetorical style emphasizes the importance of community involvement and personal experience, often contrasting with more nationally-focused political narratives.