Employee benefits for IT services and managed service providers,made easy.
85% of U.S. computer facilities management 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.
IT services at a glance
Offering benefits at an IT services company
Small IT teams cover long hours, remote sites, and clients who expect an answer. Here’s what shapes a benefits plan for an IT services company or MSP.
- of U.S. computer facilities management firms have fewer than 20 employees
- 85%
- openings a year projected for computer support specialists, 2025–2035
- 48,700
Source: BLS Occupational Outlook Handbook: computer support specialists
- of private workers in professional, scientific, and technical services have access to employer medical coverage
- 90%
Nights, weekends, and on-call
Support may need to run around the clock, so some technicians work nights or weekends. Full-time status follows average hours, 30 or more a week, not the shift someone works.
Sources: BLS Occupational Outlook Handbook: computer support specialists; IRS: identifying full-time employees
Staff in other states
You can offer one plan with a multi-state or national network, or separate plans by state, even for a single employee somewhere else. Either way, the offer goes to every full-time employee in each location.
Overflow contractors
Hiring contractors for overflow work doesn’t make you an employer, and they don’t count toward your plan. For a group plan, employees are generally the people you pay on a W-2.
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
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 IT owners ask.
Yes. You can offer one plan with a multi-state or national network, or separate plans by state, even for a single employee elsewhere. Tell us where your team is and we’ll show you what’s possible.
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?