Employee benefits for independent retail shops,made easy.
91% of U.S. retail 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.
Retail at a glance
Offering benefits at a retail shop
A core year-round team, holiday rushes, and schedules that run into evenings and weekends. Here’s what shapes a benefits plan for an independent shop.
- of U.S. retail businesses have fewer than 20 employees
- 91%
- of private workers in retail trade have access to employer medical coverage
- 55%
Source: BLS Employee Benefits in the United States, March 2026: retail trade
- average weekly hours in retail trade in 2025, just under the 30-hour full-time line
- 29.9
Source: BLS Current Employment Statistics: retail trade, 2025
Holiday hires
The IRS treats retail workers employed only for the holiday season as seasonal. Seasonal peaks of 120 days or fewer don’t make you a large employer, and SHOP coverage doesn’t have to be offered to seasonal workers.
Sources: IRS: applicable large employers; HealthCare.gov: who qualifies for SHOP
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.
Source: IRS Form 8941 instructions
Turnover
Retail workers quit at 2.6% a month in 2025, against 2.2% across private industry. A benefits package helps keep your best people through the next season.
Source: BLS Job Openings and Labor Turnover Survey, 2025 (Table 22)
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
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 shop owners ask.
Not if they’re seasonal and work 120 days or fewer. Premiums you pay for them still count toward the credit.
Tell us about your shop.
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?