Employee benefits for trucking companies,made easy.
94% of U.S. general freight trucking companies 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.
Trucking at a glance
Offering benefits to your drivers
Drivers are in demand, their health keeps them certified, and some run as owner-operators. Here’s what shapes a benefits plan for a small trucking company.
- of U.S. general freight trucking companies have fewer than 20 employees
- 94%
- openings a year projected for heavy and tractor-trailer truck drivers, 2025–2035
- 214,500
Source: BLS Occupational Outlook Handbook: heavy and tractor-trailer truck drivers
- of private workers in transportation and warehousing have access to employer medical coverage
- 86%
Source: BLS Employee Benefits in the United States, March 2026: transportation and warehousing
Owner-operators
Only common-law employees count toward your size and your plan. Federal leasing rules for owner-operators don’t decide on their own whether a driver is an employee or an independent contractor.
Sources: IRS: employer shared responsibility questions and answers; 49 CFR 376.12, lease requirements
Health keeps drivers on the road
A DOT medical certificate lasts up to 24 months, or less when a condition such as high blood pressure needs monitoring. Coverage that makes routine care easy helps drivers stay certified.
A physical job
In 2024, truck transportation recorded 2.9 injury and illness cases per 100 full-time workers, against 2.3 across private industry. Income protection and life insurance are worth a look.
Sources: BLS Survey of Occupational Injuries and Illnesses, 2024; BLS Census of Fatal Occupational Injuries, 2024
Counting toward 50
Count full-time employees plus full-time equivalents from part-timers such as dispatchers. A prior-year average of 50 or more makes you a large employer.
Sources: IRS: applicable large employers; IRS: employer shared responsibility questions and answers
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 trucking owners ask.
Only common-law employees count. Federal lease rules for owner-operators don’t decide on their own whether a driver is an employee or an independent contractor.
Tell us about your fleet.
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?