Client:
Wise Cut Landscaping
Industry:
Commercial Landscaping & Grounds Maintenance
Headquarters:
Greater Charlotte Metro Area, NC
Employees:
20+
Founded:
2010
From a Dream and a Pickup Truck to a Premier Landscape Company
In 2010, husband and wife team Tim and Stephanie launched Wise Cut Landscaping with one goal: pay their bills after the recession and build a better life. What began as a leap of faith has grown into a thriving commercial landscaping company with over 20 employees, two successful acquisitions, and a reputation for excellence across the Charlotte metro area from Rock Hill to Mooresville.
Their secret? A shared commitment to integrity, customer service, and staying in their lane both as a couple and as business partners.
Building a Business—and a Marriage—Through Shared Vision
Tim and Stephanie’s strengths complement one another. Tim sees the big picture and drives forward momentum. Stephanie brings order, detail, and follow-through. “We’ve worked side-by-side for over 15 years,” says Tim. “And the key has been understanding each other’s strengths and staying focused on our shared goals.”
That clarity of purpose has helped them weather the inevitable challenges that come with scaling a landscape contracting business challenges they’re now helping others navigate through mentorship and community involvement.
Strategic Growth: Organic Expansion and Smart Acquisitions
Wise Cut’s recent growth includes two major acquisitions that added over 70% in commercial maintenance contracts within three years. These moves have enabled the company to:
- Expand their presence across Charlotte
- Take over high-quality client contracts from retiring owners
- Offer consistent, year-round work to their crew
- Create more local jobs and career opportunities
“Our ideal client is one who values curb appeal and takes pride in how their property looks,” says Tim. “We focus on HOAs, industrial parks, and commercial properties where our quality work and attention to detail are appreciated.”
Growing with the Right Support Team
As Wise Cut Landscaping scaled, they knew success would depend on more than landscaping expertise; it would take the right systems and strategic partners.
Enter O’Connor Insurance Associates.
“O’Connor has been with us since the beginning,” Tim says. “They’ve helped us navigate every stage of growth adding employees, managing workers’ comp audits, adjusting coverage, you name it.”
As their needs evolved, O’Connor Insurance responded with:
- Comprehensive business insurance tailored for landscaping contractors
- Annual proactive coverage reviews to identify risks and opportunities
- Online tools for managing certificates and driver audits
- A responsive team that truly understands the landscaping industry
“You don’t have to know everything,” says Tim. “But you need partners who do. That’s what O’Connor Insurance brings to the table.”
What Sets Wise Cut Apart
Wise Cut Landscaping has built a strong reputation in the Charlotte community by sticking to a few core principles:
- Integrity First: “We own our mistakes and make them right,” says Tim.
- Constant Communication: Clients know they’ll always get a call back and stay in the loop.
- Team Culture: Wise Cut Landscaping invests in their crew, mentoring employees and giving them room to grow.
- Client Fit: They know who their ideal clients are—and aren’t afraid to say no to the wrong ones.
Their success hasn’t gone unnoticed. Through word of mouth, community presence, and mentorship, Wise Cut Landscaping has become a go-to name in Charlotte’s landscaping scene.
Why Landscapers Like Wise Cut Trust O’Connor
Landscaping contractors face unique insurance challenges—from managing a mobile workforce and multiple trucks to navigating seasonal work, subcontractors, and liability on commercial sites.
Wise Cut Landscaping needed a partner who understands:
- The risks landscape contractors face every day
- The importance of streamlined certificate access for job site entry
- How to tailor coverage as operations grow and evolve
- How to support a contractor’s long-term success, not just sell a policy
“O’Connor Insurance’s team is knowledgeable, proactive, and incredibly easy to work with,” Stephanie says. “They’ve earned our trust and kept it for over a decade.”
Ready to Grow? Start with the Right Partner.
If you’re a landscape contractor in North Carolina with 20 or more employees and you’re looking for a strategic insurance partner who understands your industry, your goals, and your challenges O’Connor Insurance Associates is here for you.
We don’t just sell insurance. We help landscapers grow smart.
Let’s talk about your growth plan.
Contact Us
today to schedule a landscaping insurance review.
Last updated:
O’Connor Insurance Associates is fully licensed to provide personal and commercial insurance solutions for individuals, families and businesses across North Carolina.
We proudly serve families and business owners from our office in Charlotte, North Carolina. As an independent, family-owned agency since 2000, our team works with more than one insurance company to make sure homeowners, drivers, contractors, landscapers, small businesses and other personal and commercial clients receive coverage that fits their real risks.
About the Author
President & Founder
I’m Terry O’Connor, President and Founder of O’Connor Insurance Associates. I grew up in Pennsylvania, earned my bachelor’s degree at Edinboro University and my master’s at Gannon University, and in 1998 I traded snow for sunshine and moved to Charlotte. In January 2000, I started this agency on my own because I wanted to help people protect what matters most to them. More than two decades later, we’ve grown into an independent agency serving families and businesses across North Carolina, and we’ve been recognized as an IIABA Best Practices Agency every year since 2010, a distinction held by fewer than 1% of agencies nationwide.
I’ve seen firsthand how the right protection can change a family’s or a business owner’s life, and that’s why I lead with empathy, education and honest advice. As an independent agent, I work for you, not for one insurance company. I take the time to explain your options in plain language, and when you call our office, you reach a real person who knows your account.
Outside the office, you’ll usually find me outdoors hunting or fishing, or on the mat coaching wrestling as an assistant varsity coach at Mallard Creek High School. I’m also a proud supporter of the arts, usually in the front row cheering on my daughter in local theater productions. I’d be glad to review your coverage with you. Call me at 704-510-8884 or email terry@oianc.com.
Latest Articles
