Company Benefits

Picture yourself in a career with great benefits and a team that gets you.

You aren’t one of thousands here. We know your name—and the names of your kids and pets. As a family-owned business, valuing personal connections is second nature to us. You’ll have what you need to succeed on the job and support your family at home.

Tight Freight Network

Reputation and relationships are everything to us. We retain consistent, committed volumes for our drivers, and our driver force has grown at 10% since 2016.

Best of Both Worlds

We’re a team of about 300 people, including drivers and support staff. Our size lets us provide bigger opportunities without sacrificing a family-like culture.

Driven by respect

Your perspective matters. Everyone helps drive us forward. We respect your time and talent by offering great pay, excellent benefits and company recognition.

Our team's benefits and perks

Balance work and life while laying the groundwork for your future. Whether you’re a driver or one of our support staff, you’ll get benefits that make life a little easier when you join our team. See what perks set Sky apart from other companies.


Waste less time at the loading dock.


Drivers get paid based on years of experience.

Guaranteed pay raises

Drivers earn a raise every year. We put it in writing.

Paid Time Off

Take time off when you need it.

Medical, Dental, & Vision

Access Sky’s great health benefits.


Plan for your future by investing.

Free life insurance

Support staff receive free life insurance coverage.

ID Theft Protection

Get discounts on identity theft prevention.

I highly recommended Sky Transportation! They take care of their drivers and equipment. Sky offers great routes with an awesome pay package.”

- Juanita

Let's talk about your career at Sky. Send us your resume to get started.