Employee benefits for property management companies,made easy.
90% of U.S. residential property management firms 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.
Property managers at a glance
Offering benefits at a property management company
Managers, leasing staff, and maintenance crews, some of them living on site. Here’s what shapes a benefits plan for a property management company.
- of U.S. residential property management firms have fewer than 20 employees
- 90%
- openings a year projected for property, real estate, and community association managers, 2025–2035
- 36,900
Source: BLS Occupational Outlook Handbook: property, real estate, and community association managers
- of property, real estate, and community association managers are self-employed
- 31%
Source: BLS Occupational Outlook Handbook: property, real estate, and community association managers
On-site managers
Some managers are required to live on site. Lodging you provide can be left out of their wages if it’s on your business premises, for your convenience, and a condition of the job.
Sources: BLS Occupational Outlook Handbook: property, real estate, and community association managers; IRS Publication 15-B (2026)
Part-time maintenance staff
Federal rules treat an employee who averages 30 or more hours a week as full time. A SHOP marketplace plan has to be offered to every full-time employee, and covering part-time maintenance staff is your choice.
Sources: IRS: identifying full-time employees; HealthCare.gov: who qualifies for SHOP
Employees and contractors
For a group plan, employees are generally the people you pay on a W-2. Independent contractors buy their own coverage, and hiring them doesn’t make you an employer. Whether someone is a contractor follows the IRS’s common-law test, where offering benefits is itself a factor.
Sources: HealthCare.gov: coverage for the self-employed; IRS: independent contractor or employee
If you own the business through an S corporation
Premiums for an owner with more than 2% of an S corporation are deductible by the company and reported as wages on the owner’s W-2, but they aren’t subject to Social Security or Medicare tax. The owner may then be able to deduct them personally.
Source: IRS: S corporation compensation and medical insurance
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 property managers ask.
Not if it’s on your business premises, provided for your convenience, and a condition of the job. All three tests have to be met.
Tell us about your team.
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?