CDL-A Owner-Operators - Now Hiring

Regional Owner Operator (CDL-A) | Net $3,500-$6,000/Week | Home Nightly 

Why Owner Operators Choose Cayman Express. We Handle the Heavy Lifting So You Don’t Have To 

Cayman provides a streamlined, fully supported operating environment for Owner Operators. Instead of worrying about paperwork and administrative tasks, you get: 

• Company-managed insurance options 

• Liability and cargo insurance handled through Cayman 

• Easy enrollment and competitive rates 

• No hidden fees — clean, transparent deductions 

• Compliance handled for you 

• DOT/FMCSA monitoring 

• Quarterly filings and safety documentation support 

• ELD setup and ongoing compliance assistance 

• Back-office administration 

• Weekly settlements 

• Billing, and collections managed centrally 

• Accessorials, detention, and TONU processed for you 

• No chasing customers for paperwork or payment 

• Load planning & dispatch support 

• 24/7 dispatch 

• Experienced planners who keep your truck moving 

• Optional dedicated lanes and preferred routing 

• Fuel card program and nightly fueling in yard 

• National discounts 

• Weekly deduction with no markups 

This structure lets you operate like a true business owner without drowning in administrative work. 

Compensation 

• Competitive per mile and percentage-based revenue share 

• Average weekly take-home to the truck available upon request 

• Detention, layover, and TONU all paid 

• Weekly direct-deposit settlements 

• 100% no-touch dry van freight 

What You’ll Do 

• Run OTR freight across regional lanes using your own tractor 

• Maintain safe driving practices and stay compliant with DOT requirements 

• Communicate professionally with dispatch and customers 

• Manage your driving schedule with full flexibility and support 

Requirements 

• CDL-A & valid DOT medical card 

• Own or lease your tractor (in good mechanical condition) 

• Solid safety record & acceptable MVR 

• Ability to run OTR (home daily is optional) 

• Professional and business-minded approach 

What You Get with Cayman Express 

• A partnership, not just a dispatcher 

• Transparent weekly settlements 

• Consistent lanes that keep you running 

• Reduced administrative workload so you can focus on driving 

• Access to a team that treats Owner Operators with respect 

Equal Opportunity Statement 

Cayman Express welcomes Owner Operators from all backgrounds. We do not discriminate based on race, color, religion, sex, national origin, disability, veteran status, gender identity, or any protected characteristic.