Driver Opportunities

Drive with Square Transportation

We’re hiring experienced CDL Class A drivers to run our 42-trailer Conestoga fleet across East and Southeast US lanes. Based out of Naperville, IL with consistent freight from established broker and shipper relationships.

What we offer:
– Competitive per-mile pay with weekly settlements
– Direct deposit and factoring through Assist Financial / Porter Billing
– Late-model Conestoga equipment — weather protection of dry van plus flatbed loading flexibility
– Real dispatch support, not auto-routing
– Owner-operator and lease purchase programs available

Requirements:
– Valid Class A CDL
– Current DOT medical card
– Clean MVR and PSP
– 2+ year verifiable OTR experience preferred
– Pass FMCSA Drug & Alcohol Clearinghouse query

Apply online in about 15 minutes — speak your answers or type them. Our AI walks you through every question.