In this post, we’ll look at the specific factors underwriters evaluate when reviewing landscaping and sitework operations. You’ll learn what makes this niche stand out, how to prepare for underwriting reviews, and what steps you can take to strengthen your risk profile.
The first thing underwriters want to understand is how your landscaping or sitework business is built, from the ground up. Before they look at equipment, safety records, or jobsite details, they zero in on your business structure and your team’s experience. Why? Because a well-established, clearly organized business with a seasoned leadership team signals stability and lower risk.
Years in business is often one of the earliest questions asked. If you've been operating for a decade with a consistent track record, that holds weight. On the other hand, if your company is relatively new, underwriters will dig deeper into your leadership’s industry background. They’re looking for indicators that you know how to handle the challenges that come with site preparation, soil conditions, grading, drainage, and hardscape work. In other words, experience matters, but so does how that experience is structured across your organization.
They’ll also look at whether you operate as a sole proprietorship, LLC, S-Corp, or partnership. Each of these structures carries different levels of liability protection and management oversight, which impacts how your business is assessed during underwriting for contractors. If there’s shared ownership, underwriters will want to see who’s responsible for what. Are project managers trained in risk mitigation? Does leadership have a strong operational background, or are they absentee owners?
Another key area of focus is your company’s history with high-risk services. For example, if your business handles excavation, retaining wall construction, or operates near utilities, underwriters will flag these as heightened exposures. They may require more detailed information, like permits pulled, qualifications held, or subcontractor vetting processes. If you subcontract any portion of this work, your agreements and insurance transfer protocols will come under the microscope.
Having a clear organizational chart, detailed job descriptions, and a company resume showing past projects can be incredibly useful during the process. These not only show that your business has structure, but they also demonstrate that you've thought critically about how to manage operational risk, something that’s central to underwriting for contractors in this field.
This stage sets the tone. A strong business foundation gives underwriters confidence in everything else that follows, from your safety protocols to your equipment maintenance strategy.
Underwriters don’t just want to know that your landscaping or sitework business gets the job done, they want to know that it gets done safely. Safety protocols and risk management practices are front and center in underwriting for contractors because they directly affect the likelihood and severity of claims. And in industries where crews operate heavy machinery, navigate uneven terrain, or work around utilities, even small oversights can lead to big losses.
One of the first things underwriters want to see is whether your team has a documented safety program. A one-page safety mission statement isn’t going to cut it. They’re looking for real-world systems: training schedules, incident reporting procedures, equipment checklists, and clearly defined responsibilities for safety enforcement. If you’ve invested in third-party safety audits or use digital tools to track compliance, that’s even better, it shows that safety isn’t just a policy, it’s a daily practice.
Training is another major focus. Are your crew members trained in trench safety, equipment operation, and hazard identification? Do you run toolbox talks before shifts? Are supervisors held accountable for enforcement? Underwriters want to see that safety isn't just talked about at the top, but is part of the culture across every jobsite. It’s not enough to say you’re OSHA compliant, what matters is how you keep that compliance alive in the field.
Incident history plays a role too. If you’ve had claims in the past, underwriters will look closely at what caused them and what you did in response. Did you update your procedures? Retrain your crew? Add new controls? Demonstrating a pattern of learning and improvement shows underwriters that you take risk seriously and know how to respond when things go wrong.
Underwriting for contractors in landscaping and sitework often comes down to how much control you have over unpredictable environments. Whether it’s shifting soil, deep excavation, or uneven terrain, your ability to anticipate hazards and put preventive measures in place can make a significant difference in how you’re assessed. That’s why clear protocols, consistent training, and a commitment to safety leadership aren’t just best practices, they’re essentials in the eyes of an underwriter.
When it comes to underwriting for contractors in the landscaping and sitework space, your equipment and vehicle management tells a bigger story than most business owners realize. To an underwriter, how you operate and maintain your fleet is a direct reflection of how seriously you take risk. Whether you’re running skid steers, dump trucks, backhoes, or hydroseeders, the way your equipment is handled plays a central role in your risk profile.
One of the first things underwriters evaluate is your inventory. What types of equipment do you own? What’s leased? What’s operated by employees versus subcontractors? A business that owns and regularly uses heavy machinery comes with a higher potential for property damage or injury, especially if that equipment is used in high-traffic or residential areas. But that doesn’t mean you’ll be penalized, if you can show strong controls and maintenance habits, that risk becomes more manageable in the eyes of an underwriter.
Maintenance records are critical. Underwriters want to see proof that your machinery is regularly inspected, serviced, and repaired by qualified personnel. A single overlooked issue, like worn hydraulic lines or faulty brakes, can lead to expensive claims. If you’re using preventive maintenance software or keep detailed logs of all inspections and service intervals, that adds credibility and shows that equipment safety isn’t left to chance.
Vehicle use is also heavily reviewed. Landscaping and sitework businesses often operate fleets of trucks, trailers, and utility vehicles, and underwriters are interested in how those assets are managed. Do you have a driver safety program? Are motor vehicle records reviewed before hiring? Is GPS tracking used to monitor routes, speeding, or idling? These are the kinds of details that can shift the tone of the underwriting conversation, from risk exposure to risk control.
Another area underwriters look at is how equipment is stored and secured. Are machines left on open jobsites overnight? Do you use fencing, cameras, or geofencing for theft prevention? Equipment theft and vandalism are common in this industry, and showing that you’ve taken steps to reduce those risks helps position your business more favorably during underwriting for contractors.
This part of the process is all about showing that you don’t just own expensive machinery, you operate it responsibly. A strong maintenance program, a reliable fleet management strategy, and a thoughtful approach to equipment security all build confidence with underwriters and can contribute to better coverage terms or pricing.
The nature of your work sites and how you manage your contracting processes is another area of focus during underwriting for contractors. Landscaping and sitework companies often operate across a range of environments, from tight residential spaces to sprawling municipal projects, and the complexity of these jobs can carry very different risk profiles.
Underwriters want to know what types of jobs you take on. Are they mostly residential grading and sod installs? Or are you handling large-scale drainage projects, commercial retaining walls, or highway erosion control? The scope and value of your projects, along with their geographic location, give underwriters insight into your exposure levels. Larger or more complex jobs typically mean higher limits and stricter requirements.
How you work with subcontractors matters too. If you hire subcontractors to handle excavation, concrete, or electrical work, underwriters will want to see how those relationships are managed. Are contracts in place that transfer risk properly? Do you require certificates of insurance with specific limits and endorsements? A strong subcontractor vetting and documentation process reduces the chance that your business ends up liable for someone else’s mistake.
Past claim history related to jobsites is another important factor. If you’ve had issues with drainage failures, utility strikes, or soil erosion, underwriters will ask how you handled it and what’s been done to prevent similar outcomes. They’ll also want to know if you document site conditions, use site-specific safety plans, or conduct pre-construction assessments.
During underwriting for contractors, the goal is to paint a picture of a business that understands where its risks lie, and knows how to manage them. The more transparent and organized you are with your contracting practices, the more confident underwriters will be in quoting your policy.
Underwriting for contractors in landscaping and sitework isn’t just about ticking boxes, it’s about showing that your business is built on solid ground. Underwriters are looking for a strong organizational structure, a clear commitment to safety, a responsible approach to equipment and vehicle use, and jobsite practices that limit risk rather than invite it. The more you can demonstrate professionalism and consistency in these areas, the more control you’ll have over the insurance terms you’re offered.
If you're looking to strengthen your coverage or want to better understand what underwriters are seeing when they evaluate your business, it may be time to reassess your current risk profile. For tailored protection and a clear explanation of how your operations are evaluated, take a look at this guide to Landscaping Contractor Insurance. It’s a great place to get practical answers and make sure your business is protected from every angle.