Flanagan’s Contracting Group of Hillsborough Township, New Jersey, started with a high school couple, a mower and chainsaws.
Today, Bob Flanagan and his wife, Christine, have transformed the company from a landscape maintenance contractor to a full-service construction firm with 35 employees and $18 million to $20 million in annual revenue. The company can handle just about everything except plumbing and electrical, transforming sites from brownfields to flourishing community centers. It was named one of 12 finalists for Equipment World’s 2025 Contractor of the Year Award.
Christine’s financial creativity has gotten Flanagan’s through tough times, and Bob’s hustle and mechanical aptitude have enabled the company to expand into new markets.
In the 1980s, Bob’s brother, Roger, joined the company as a co-owner and estimator. When residential work dried up in the '90s, Roger secured some large municipal projects in the area, from pedestrian bridges to large athletic complexes and parks.
Bob Jr., who spent his childhood hanging out at the office and on jobsites, earned a degree in civil engineering and joined his parents and uncle full-time as a project manager. He has been a technology champion, introducing 3D machine control and, more recently, a tiltrotator, to increase efficiency and production. Bob Jr’s wife, Jackie, also works for the company as its human resources manager.
In the video above, Bob, Roger and Bob Jr. talk about the company’s evolution from landscaping to large, publicly funded projects, building relationships with engineers and project owners and investing in the latest technology.
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