Small business health insurance in Wisconsin,made easy.
Small businesses employ nearly half (48.0%) of Wisconsin’s 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.
Wisconsin at a glance
Offering health benefits in Wisconsin
Wisconsin has 497,370 small businesses, and about one in three small employers offers health insurance. Here’s what shapes a small group health plan in Wisconsin.
- small businesses in Wisconsin
- 497,370
Source: SBA Office of Advocacy, 2025 Small Business Profile: Wisconsin (2022 data)
- of workplaces at firms under 50 employees offer health insurance
- 32.0%
- average yearly premium for single coverage at firms under 50 employees
- $9,260
Who counts as a small group
Wisconsin law defines a small employer as one with 2 to 50 employees, with at least 2 on the first day of the plan year.
Source: Wis. Stat. § 635.02
Continuation coverage at any size
Wisconsin’s continuation law applies to insured group plans whatever your size, not only above 20 employees. Employees covered for at least 3 months can continue for up to 18 months. Where federal COBRA also applies, the state’s insurance office says the rule more favorable to the employee applies.
You can start any month
Insurers must offer small group coverage all year. If your team doesn’t meet an insurer’s minimum participation or contribution rules, it can limit you to enrolling between November 15 and December 15, when those minimums can’t be applied.
Source: 45 CFR 147.104
The small business tax credit
The federal small business health care tax 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, but only for coverage bought through the SHOP marketplace. For 2026, HealthCare.gov lists SHOP medical plans from one insurer in 34 Wisconsin counties. If your business is in one of them, the credit may be an option; your tax advisor can confirm.
Sources: 26 U.S.C. § 45R; IRS Rev. Proc. 2025-32; HealthCare.gov 2026 SHOP plan data
Alternatives to a group plan
Some small businesses reimburse employees for individual coverage instead. A QSEHRA is for employers with fewer than 50 full-time employees that don’t offer a group plan; in 2026 it can reimburse up to $6,450 a year for an employee alone, or $13,100 with family. An ICHRA, which HealthCare.gov now calls a CHOICE arrangement, works at any size and has no reimbursement cap.
Sources: IRS Notice 2017-67; IRS Rev. Proc. 2025-32; HealthCare.gov: individual coverage HRAs
Who oversees your plan
Insured small group plans in Wisconsin are overseen by the Office of the Commissioner of Insurance. Self-funded plans fall under federal rules instead.
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 Wisconsin employers ask.
Wisconsin law defines a small employer as one with 2 to 50 employees, with at least 2 on the first day of the plan year (Wis. Stat. § 635.02). We can help you work out where your business fits.
Tell us about your Wisconsin 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?