Employee benefits for startups and tech companies,made easy.
91% of U.S. software and IT services firms 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.
Startups at a glance
Offering benefits at a startup
You’re hiring against companies with full benefits teams, often with people in more than one state. Here’s what shapes a benefits plan for a startup or small tech company.
- of U.S. software and IT services firms have fewer than 20 employees
- 91%
- openings a year projected for software developers, QA analysts, and testers, 2025–2035
- 106,100
Source: BLS Occupational Outlook Handbook: software developers, quality assurance analysts, and testers
- 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
A team in more than one state
A small group plan is set up in the state of your main business location. You can offer one plan with a multi-state or national network, or separate plans by state, even for a single employee somewhere else. Tell us where your team is and we’ll show you what’s possible.
Founders on the plan
Founders can be covered, as long as at least one employee who isn’t an owner, partner, or family member also enrolls.
Source: HealthCare.gov: SHOP overview
Reimbursing individual coverage instead
An individual coverage HRA (ICHRA), which HealthCare.gov now calls a CHOICE arrangement, lets you reimburse employees for their own individual plans, at any company size, with offers that can differ by where people work. A QSEHRA is the capped version for employers with fewer than 50 full-time employees.
Sources: HealthCare.gov: individual coverage HRAs; IRS Notice 2017-67
A PEO or your own plan
A professional employer organization handles payroll administration and tax reporting for its clients, and many bundle benefits in. If you’re weighing a PEO against a plan of your own, we’ll walk you through the difference.
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 founders ask.
Yes. You can offer one plan with a multi-state or national network, or separate plans by state, even for a single employee in another location. You could also reimburse individual coverage through an ICHRA, now called a CHOICE arrangement.
Tell us about your 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?