Rockwell Insurance Agency
Agency Owner
Holland Rockwell
Location
35 Pritham Avenue, Greenville, ME
Open
Monday – Friday | 9:00 .m. – 4:00 p.m.
Website
Opening and running a business is a family trait for Holland Rockwell of Greenville. The owner of Rockwell Insurance Agency at Lakeside on Pritham Ave., Holland learned entrepreneurship from her parents and extended family. “My father always had multiple businesses and my mom ran a bed and breakfast out of her home,” recalled Holland, who waitressed at Auntie M’s as a 12-year-old, a former Greenville restaurant owned by her grandmother and aunt. “By age 8 I had great phone and communication skills because clients would call our house. Work has always been intertwined with my personal life.”
Holland’s upbringing prepared her well for a career that has encompassed a variety of skills, from snowboard instructor at Sugarloaf to U.S. Operations Training Director at Vacasa vacation homes and rentals. In April 2024, after a stint as an Allstate insurance agent, Holland decided she wanted to open her own insurance business. Her experiences helped guide her, especially when it came to leadership. “The best leaders are flexible, understanding, gracious, and humble,” said Holland, who now has four employees at her agency which offers personal, business, and life insurance. “Don’t let pride get in the way of good decision making.”
Outside of work Holland and her husband Alex, owner of Reel Moosehead Guide Service in Greenville, homeschool their two children, ages 4 and 8, and snow ski, hunt, fish, waterski, and more. Holland was the Race Director for the inaugural Moosehead Marathon this spring which attracted 230 race registrants and 197 confirmed race finishers. In her ‘spare time’, Holland – who has completed six half-marathons – says she might make 2026’s Moosehead Marathon her first full marathon experience! Learn more about Holland and her insurance agency at TheRockwellAgency.com.
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