Employee benefits for private schools and tutoring centers,made easy.
90% of U.S. schools and instruction businesses 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.
Schools and tutoring at a glance
Offering benefits at a school or tutoring center
Small schools compete with public districts for teachers, and many tutors work part time or on contract. Here’s what shapes a benefits plan for your team.
- of U.S. schools and instruction businesses (outside colleges and K–12 districts) have fewer than 20 employees
- 90%
- of private workers in educational services have access to employer medical coverage, against 99% of public school teachers
- 71%
Source: BLS Employee Benefits in the United States, March 2026: educational services
- median pay for private elementary school teachers, against $65,260 in public schools
- $58,140
Source: BLS Occupational Outlook Handbook: kindergarten and elementary school teachers
Competing with public schools
99% of public school teachers have access to employer medical coverage, against 71% of private workers in educational services. Benefits help a private school or center close some of that gap.
Source: BLS Employee Benefits in the United States, March 2026: educational services
Tutors on contract
Whether a tutor is a contractor depends on control: the IRS weighs behavioral, financial, and relationship factors, and Form SS-8 gets a ruling.
Part-time and substitute teachers
A SHOP marketplace plan has to be offered to full-time employees, 30 or more hours a week. Covering part-time or substitute teachers is your choice.
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 school owners ask.
A group plan covers employees, generally the people you pay on a W-2. Independent contractors buy their own coverage, through the Marketplace for example. Whether someone is a contractor follows the IRS’s common-law test.
Tell us about your school.
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?