Employee benefits for law firms,made easy.
95% of U.S. law offices 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.
Small law firms at a glance
Offering benefits at a small law firm
Small firms compete with large ones for attorneys and paralegals, and partners have their own tax rules. Here’s what shapes a benefits plan for a firm like yours.
- of U.S. law offices have fewer than 20 employees
- 95%
- of private workers in professional, scientific, and technical services have access to employer medical coverage
- 90%
Source: BLS Employee Benefits in the United States, March 2026
- openings a year projected for paralegals and legal assistants, 2025–2035
- 40,800
Source: BLS Occupational Outlook Handbook: paralegals and legal assistants
Competing with bigger firms
90% of private workers in professional, scientific, and technical services have access to employer medical coverage, against 55% at workplaces with fewer than 50 workers across industries. Benefits are part of how a small firm keeps pace.
Source: BLS Employee Benefits in the United States, March 2026
Partners on the plan
A partnership reports partners’ health premiums as guaranteed payments, and partners include them in income. A partner can deduct them personally only if the partnership pays or reimburses them and reports them, and not for any month the partner could join another subsidized plan, such as a spouse’s.
Sources: IRS Form 1065 instructions; IRS Form 7206 instructions
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
You need at least one employee
A SHOP marketplace plan needs at least one employee who isn’t an owner, partner, spouse, or family member. Owners also don’t count toward the small business tax credit’s limits.
Sources: HealthCare.gov: who qualifies for SHOP; IRS Form 8941 instructions
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 firm owners ask.
Generally, yes. The partnership reports them as guaranteed payments, the partner includes them in income, and the partner may deduct them personally, provided the partnership pays or reimburses them and reports them, and the partner isn’t eligible for another subsidized plan that month.
Tell us about your firm.
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?