Truck Driver Jobs in Sheboygan, WI
Looking for truck driver jobs in Sheboygan that offer more than just a paycheck? At Service One Transportation, we know what matters most to drivers — respect, reliability, and rewards that go beyond the road. Whether you’re an experienced driver or just getting started, you’ll find a welcoming team, competitive pay, and unbeatable benefits with a family-owned company that puts people first.
Drive Local, Earn Big — Right Here in Sheboygan
Sheboygan isn’t just home to beautiful lakefront views and vibrant communities — it’s also a prime hub for professional drivers. With Service One Transportation, you can enjoy the advantages of working with a local, Wisconsin-based company that understands the unique needs of Sheboygan truck drivers.
From flexible routes to dedicated support, we’re proud to provide career opportunities that keep drivers close to home and connected to what matters.
About Service One Transportation
Service One is a family-owned and operated transportation company based in Plymouth, Wisconsin — just a short drive from Sheboygan. For over two decades, we’ve built our reputation on being dependable, honest, and driver-focused.
Our commitment to safety, integrity, and timely service has earned us the trust of our customers and the loyalty of our drivers. We don’t believe in being the biggest — we believe in being the best, one driver at a time.
What You’ll Get with Service One
If you’re exploring truck driver jobs in Sheboygan, here’s why Service One should be your first stop:
- Excellent per mile pay (based on OTR experience)
- Paid vacations & holidays
- Top-tier medical, dental, vision, and life insurance
- 401K with company match
- Short term & long term disability
- Performance bonus opportunities
- Access to our health and wellness center
- Family rider program — pets included!
- Finishing program for new drivers
Whether you’re looking for over-the-road (OTR) runs or want to stay closer to Sheboygan, we offer flexible options to match your lifestyle and career goals.
Why Sheboygan Drivers Choose Service One
At Service One, you’re more than a number — you’re part of the family. Unlike large carriers, we take the time to know our drivers by name, not by truck number. We prioritize on-time delivery and on-time support — for our customers and for you.
Our drivers choose us because we offer:
- Stability – We’re a financially sound company with long-standing customers and consistent freight.
- Respect – We value communication, honesty, and mutual respect above all else.
- Local Roots – Being based near Sheboygan allows us to stay connected to the drivers and communities we serve.
- Supportive Environment – From dispatch to maintenance, our team is here to help you succeed every mile of the way.
Looking for truck driver jobs in Sheboygan where you’re supported from day one? Service One is your home on the road.
Ready to Hit the Road with Service One?
Now’s the time to take the wheel of your career. If you’re searching for truck driver jobs in Sheboygan that offer top pay, unmatched benefits, and a company that treats you like family, Service One Transportation is ready to welcome you aboard.
Join a team that puts drivers first and delivers on its promises — always on time.
Apply Now and take the next step toward a better driving career with Service One.