Employee benefits for real estate brokerages,made easy.
99% of U.S. real estate brokerages 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.
Brokerages at a glance
Offering benefits at a real estate brokerage
Most agents are independent, but the staff who keep a brokerage running are employees. Here’s what shapes a benefits plan for a brokerage.
- of U.S. real estate brokerages have fewer than 20 employees
- 99%
- of real estate brokers are self-employed
- 55%
Source: BLS Occupational Outlook Handbook: real estate brokers and sales agents
- openings a year projected for real estate brokers and sales agents, 2025–2035
- 40,400
Source: BLS Occupational Outlook Handbook: real estate brokers and sales agents
Agents are usually self-employed
Licensed real estate agents are statutory nonemployees, self-employed for federal tax, when their pay is tied to sales rather than hours and a written contract says they won’t be treated as employees. A group plan covers employees, so agents usually buy their own coverage.
Sources: IRS: statutory nonemployees; HealthCare.gov: coverage for the self-employed
Your staff count
Office managers, transaction coordinators, and other W-2 staff are the employees a group plan is built around. Independent agents don’t count toward your size.
The 30-hour line
Federal rules treat an employee who averages 30 or more hours a week as full time. A plan bought through the SHOP marketplace has to be offered to every full-time employee, but not to part-time staff.
Sources: IRS: identifying full-time employees; HealthCare.gov: who qualifies for SHOP
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 brokers ask.
If they meet the IRS conditions for statutory nonemployees, they’re self-employed for federal tax rather than W-2 employees, and a group plan covers employees. Agents can buy coverage through the Marketplace.
Tell us about your brokerage.
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?