Employee benefits for landscaping companies,made easy.
94% of U.S. landscaping companies have fewer than 20 employees.
You want great benefits for your team. You don’t have the time or the resources to get them.
That isn’t on you. For decades, the benefits industry has been built for big companies, and small businesses have been left to figure it out alone. Cakewalk was built for you.
How it works
You run your business. We handle the benefits.
Tell us about your business.
Start with your business name. We fill in what we can find. Connect payroll and your team comes with it.
Hundreds of options. One tailored package.
We compare hundreds of plans for your team. You get one package, priced and ready to adjust.
We get your team covered.
We invite your team. You see who has started. Each person gets help choosing. Everyone is covered.
Benefits admin. Off your plate.
New hires and departures sync from payroll. Each employee gets a benefits wallet. Their questions come to us, not you.
Your benefits team. On the house.
You pay for coverage. Insurance carriers pay us a commission, so we can handle everything from building your package to supporting your team year round, at no cost to you.
Landscaping at a glance
Offering benefits with seasonal crews
Busy springs and summers, quiet winters, and a core team you want back every year. Here’s what shapes a benefits plan for a landscaping company.
- of U.S. landscaping companies have fewer than 20 employees
- 94%
- H-2B seasonal positions certified for landscaping and groundskeeping in fiscal 2025, 38% of the program
- 89,013
Source: Department of Labor, H-2B program statistics, FY2025
- average weekly hours in landscaping services in 2025
- 39.0
Source: BLS Current Employment Statistics: landscaping services, 2025
Seasonal crews
A SHOP marketplace plan has to be offered to full-time employees, not seasonal or part-time workers. Seasonal peaks of 120 days or fewer don’t make you a large employer.
Sources: HealthCare.gov: who qualifies for SHOP; IRS: applicable large employers
Seasonal workers and the tax credit
For the small business tax credit, workers employed 120 days or fewer are left out of your employee and wage counts, but premiums you pay for them still count toward the credit.
A physical job
In 2024, landscaping services recorded 3.0 injury and illness cases per 100 full-time workers, against 2.3 across private industry. Income protection is worth a look for a crew outdoors all day.
Sources: BLS Survey of Occupational Injuries and Illnesses, 2024; BLS Census of Fatal Occupational Injuries, 2024
Keeping your core team
Grounds maintenance work is projected to have 162,500 openings a year from 2025 to 2035. The people who come back every season are worth holding on to.
Source: BLS Occupational Outlook Handbook: grounds maintenance workers
Benefits are your choice under 50
Employers with fewer than 50 full-time employees, counting full-time equivalents, aren’t subject to the federal requirement to offer coverage. Offering benefits is a decision you make for your team, not a mandate.
Source: IRS: applicable large employers
The small business tax credit
The federal credit can cover up to 50% of premiums for employers with fewer than 25 full-time equivalent employees and average wages under $68,200 in 2026, if you pay at least half of employee-only premiums and buy through the SHOP marketplace. Owners and their families don’t count toward the totals. SHOP plans aren’t offered everywhere, so check your state’s guide.
The whole benefits package.
Medical, dental, vision, life insurance, and income protection. Built around your business and the people who power it.
Start with your team’s needs and your business’s budget. Explore medical coverage online, or work with a benefits advisor to understand your options and choose your next step.
Questions landscaping owners ask.
Not on a SHOP marketplace plan: coverage has to be offered to full-time employees, not part-time or seasonal workers, though you can choose to include them. And seasonal peaks of 120 days or fewer don’t make you a large employer.
Tell us about your crew.
We’ll follow up to learn about your business and walk you through your options. There’s no cost to work with us.
Prefer to start on your own?