Roger Flanagan (left) and Bob Flanagan (right), owners of Flanagan's Contracting Group.
Equipment World
Equipment WorldBob Flanagan Sr. launched his landscaping business at age 17 after finding a loophole in his high school’s co-op program.
He knew he enjoyed working outdoors, but what he really loved was the chance to leave school at 9 a.m. each day to make money, with no supervisor looking over his shoulder.
“I just couldn’t take bosses,” Bob says and laughs.
“He always beat to his own drum, and he still does,” added his wife, Christine, with a smile.
Christine would join Bob on her lunch break to help him limb and fell trees. “Flanagan’s here!” her classmates would yell when Bob pulled up in the parking lot for her.
The couple made such a good pair – in love and business – that after graduation, they got married and went all-in on the landscaping venture. And just like that, Flanagan’s Lawn & Garden Service was born.
To really grow the business, Bob and Christine realized they needed more than just muscle and mowers, so they used their gifted wedding money to buy a backhoe and a trailer.
Today, the full-service contractor, now known as Flanagan’s Contracting Group, employs around 35 people and generates $18 million to $20 million in annual revenue. The team can handle almost any site development task, from land clearing to final build, transforming brownfields into flourishing community centers in the Hillsborough Township, New Jersey area.
Ask any client and they’ll say the same thing: the Flanagans don’t miss a detail. “I’m impressed with Flanagan’s project management,” says one. “They are responsible, knowledgeable, methodical, efficient, and there are very few mistakes.”
“They maintained open communication with our team, updating us on every project phase and ensuring clarity on timelines and budget considerations. When we encountered unexpected site challenges, Flanagan’s quickly adapted the plan to keep us on schedule,” added another.
For those reasons and more, Flanagan’s Contracting Group was named a finalist for Equipment World’s 2025 Contractor of the Year award.
Equipment WorldGrowing a Family and the Business
Bob and Christine started off working side by side in the field, constructing landscape design-builds, retaining walls and sidewalks and later adding a maintenance division that managed 75 properties.
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When their second child, Bob Jr., arrived, Christine traded in her work boots for the check register, moving into the office to manage the company’s finances.
Times weren’t always easy, but Christine’s knack for numbers and creative budgeting kept the company afloat. “I always told my son, 'You could do $50 million a year and lose your shirt, or you could do $10 million and have a really great year,'” she says. “It’s all about that profitability and cash flow.”
Meanwhile, Bob’s relentless work ethic and mechanical aptitude enabled the company to keep expanding into new markets. “For some reason, we have this 'Flanagan talent' that if we’ve seen a certain type of work get done, we can just do it,” says Bob. “We don’t let anything stop us.”
In the 1980s, those capabilities expanded further when Bob’s brother, Roger, joined as a co-owner and estimator. When residential work dried up in the '90s, Roger helped the company pivot, landing some large municipal projects that would define the next chapter – pedestrian bridges, large athletic complexes and community parks.
“The economy tanked, so we decided to move on and get bigger. Municipal work was steadier at the time,” says Bob. “And Christine has been the driving force for the paperwork side of the world with the certified payrolls and other reports that you have to provide for those types of projects.”
Bob Jr., who spent his childhood hanging out at the office and on jobsites, earned a degree in civil engineering before joining the family business 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, making Flanagan’s Contracting Group a true family affair.
Equipment WorldSteady Employee Base
Managing all of the work in-house, except for plumbing and electrical, has made it easier for Flanagan’s to win bids and stay on top of deadlines. “Everything is controlled here, and we sub very little out, so you don’t have that problem of waiting on another contractor,” says Bob Sr.
The company runs four to five crews at a time, with all employees cross-trained to perform any task. Crews like the variety that comes with managing a project from start to finish, Christine says.
“There’s a wide range of different items that need to get completed, and I think the guys like that. They like that thrill of taking a blank slate and making it into something.”
“All our jobs are very different, and that’s something that people appreciate, that they’re not just on a paving crew all summer,” adds Bob Jr.
Implementing twice-weekly Zoom meetings on Tuesdays and Thursdays has helped improve communication and morale. “Before the shift, we go over what’s going on and what’s coming up, just so everyone is aware,” says Bob Jr. “We’ve found that’s made a big change in people’s attitudes because they understand the ‘why’ behind decisions, and we can sense when storms are brewing.” An email suggestion box also allows employees to provide anonymous feedback to leadership.
Flanagan’s relies on union labor but offers additional benefits to keep employees happy and engaged – from year-end bonuses to flexible time off and company fishing trips. Many employees have served for 20 years or more by the time they retire.
“Our team and the quality of work that they put out is why people like working with us,” says Christine. “We’re not constantly changing project managers. They know what to expect, what we expect, and they pretty much run their own shows, with Bob, Roger and Bob Jr. there to put out the fires and guide them along the way.”
Equipment WorldOn Top of Tech
Staying current with technology has been another big advantage for Flanagan’s. Bob Sr. and Roger got started with 2D grade control in the '90s to more accurately grade fields and running tracks, but it was Bob Jr. who has been the driving force for further integration in the office and field.
“Bobby was the breath of fresh air that they needed to really push into technology,” says Jackie.
“Around 2015 and 2016, I was just seeing that GPS was going to be the way to go to really get to the next level and improve what we’re doing,” says Bob Jr. “So, I just said, ‘We need to do this. It’s going to save us a lot of time and headaches.’”
Within months of entering 3D control, the company bought a second base and rover setup. Now, Flanagan’s has three base stations and rovers, three dozers that have GPS, two excavators with GPS and a third that’s indicate-only.
“We’ve really embraced it now,” he says.
Bob Jr. says his key to success is “not being afraid to break something.”
“Anything can be fixed,” he adds and laughs.
Both Roger and Bob Jr. are self-taught in Trimble Business Center and have equipped their team to use laptops and tablets in the field, ensuring the latest plans are always available.
The company also recently purchased a Cat 315 excavator with an Engcon tiltrotator, which will be ideal for park jobs that require creating rain gardens and bioswales.
“Some of the grading we do is smaller than where you can get a dozer in, so it’s just nice to be able to have that feature where you can tilt the bucket,” says Bob Jr. “It’s also going to be connected to the GPS. It just fits really well with what we do.”
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