Small business health insurance in Tennessee,made easy.
Small businesses employ 41.5% of Tennessee’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.
Tennessee at a glance
Offering health benefits in Tennessee
Tennessee has 741,196 small businesses, and fewer than three in ten small employers offer health insurance. Cakewalk is based in Signal Mountain, so this one is home.
- small businesses in Tennessee
- 741,196
Source: SBA Office of Advocacy, 2025 Small Business Profile: Tennessee (2022 data)
- of workplaces at firms under 50 employees offer health insurance
- 28.7%
- average yearly premium for single coverage at firms under 50 employees
- $8,365
Who counts as a small group
Tennessee follows the federal definition: a small employer has 1 to 50 employees, with at least 1 on the first day of the plan year.
Source: Tennessee Department of Commerce & Insurance, Bulletin 15-01
Continuation coverage
Tennessee repealed its state continuation law for small groups in 2025. Federal COBRA still applies once you have 20 or more employees, so it’s worth planning for as you grow.
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 no SHOP medical plans in Tennessee, so new claims there are unlikely. 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 Tennessee are overseen by the Insurance Division of the Tennessee Department of Commerce & 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 Tennessee employers ask.
Tennessee follows the federal definition of a small employer: 1 to 50 employees, with at least 1 on the first day of the plan year. We can help you work out where your business fits.
Tell us about your Tennessee 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?