Sign up to access all features of our service.
  • Job search
  • Favorites
  • Create a CV
    New
  • Salaries
  • Subscriptions

Truck Driver Owner Operator - 1yr EXP Required - OTR - Bennett Motor Express

Bennett Motor Express

CDL-A Owner Operators | Open Deck Division | Earn 74.7% of Linehaul.

CDL-A Owner Operators – Open Deck Division | Drive for yourself. Partner with a company that stands for something bigger.

At Bennett Motor Express, we don't just offer freight — we offer freedom, family, and a foundation of faith that's helped independent contractors thrive for more than 50 years. Founded by Marcia Taylor in 1974 and still family-owned and operated, Bennett is built on the belief that when we put people first, everything else follows. We proudly serve America with integrity, patriotism, and excellence — and we treat every contractor like part of our own.

We're looking for CDL-A Owner Operators who want more than just miles. If you're ready to run your business, keep more of what you earn, and partner with a company that shares your values, there's a place for you here.

Divisions Now Hiring:

  • Flatbed
  • Step Deck
  • Heavy Haul

What You'll Get:

✅ Orientation Bonus – $1,000

✅ Fast Pay – Every day can be payday

✅ Earn up to 74.7% of line haul revenue

✅ Industry-Leading Fuel Discounts – Save ~$5,000/year on average

✅ No Forced Dispatch – You choose your loads

✅ Tire & Parts Discounts

✅ Safety Bonus – Up to $3,000 annually

✅ Business Support – Accounting, load alerts & back-office help

✅ 24/7 Chaplain Support – Because your spirit matters too

✅ Pet & Rider Programs – Bring family along for the ride

✅ Virtual or In-Person Orientation – Your choice

✅ Medical Insurance Program Options

Limited availability – Apply today!

Requirements:

  • CDL A
  • 1 year of Verifiable OTR CDL A Experience

Why Contractors Choose Bennett:

  • Faith-based, family-first culture
  • You're in business for yourself, not by yourself
  • We exist to serve people, create opportunity, make a difference, and honor God in all we do
  • We believe in loyalty, safety, financial strength, and giving back to the communities we serve

At Bennett, you don't just lease on — you level up. Let's build something meaningful together.

Vacancy posted 2 hours ago
Similar jobs that could be interesting for youBased on the Truck Driver Owner Operator - 1yr EXP Required - OTR - Bennett Motor Express in Milwaukee, WI vacancy
  • $240k

     ...CDL A Solo/Team OTR Tractor Owner Operator. CEVA Freight LLC - Line...  ...-On Bonus for Team Drivers $3,000 Sign-On...  ...purchase: Liability, Non-Trucking, Physical Damage,...  ...hook freight Requirements ~ Tractors must...  ...gender identity or expression, sexual orientation,... 
    Suggested
    For contractors
    Relocation package

    CEVA Logistics

    Milwaukee, WI
    3 hours ago
  • $160k - $200k

     ...Class A CDL Owner Operator Truck Drivers. Keep Your Truck Moving. Keep More of What You Earn. You're not just looking for another load, you...  ...Minimum age of 23 years Meet all DOT qualification requirements Why Forward? Forward is built on a foundation of Independent... 
    Suggested
    Weekly pay
    For contractors
    Flexible hours

    Forward Air, Inc.

    Milwaukee, WI
    10 minutes ago
  • $260k - $364k

     ...Owner Operator Opportunities IMPORTANT UPDATE:...  ...jumping since 2018. DSL Express is NOW HIRING...  ...Gross Pay: Expect OTR avg Gross 5K to 8...  ...market. Team drivers make about 1.7 times...  ...who have reliable trucks! We want good...  ...Must have 2+ yrs CDL Exp. Must have Clean... 
    Suggested
    Weekly pay
    Contract work
    Immediate start
    Night shift
    Afternoon shift

    DSL Express

    Milwaukee, WI
    5 days ago
  • $275k - $300k

     ...Waste & Roll Off CDL-A Drivers: Regional & OTR Routes. H - Hazardous Materials Endorsement...  ...CDL - A Waste and Roll Off Truck Drivers - Seeking Company Drivers & Owner Operators! Are you ready to embark...  ...every terminal location Requirements: ~1 year tractor trailer... 
    Suggested
    Relocation package
    Flexible hours

    ACTION RESOURCES

    Milwaukee, WI
    3 hours ago
  • $1,650 per week

     ...Job Description Job Description Solo Drivers: 2,000+ Miles Per Week On Average Up to $7,500 Sign On Bonus Top 20% of our OTR Drivers earn $1,650 Weekly Team Drivers...  ...~ Consistent Miles & Freight with this truck driving job Qualifications: Must have... 
    Suggested
    Temporary work
    Relocation package
    Flexible hours

    U.S. Xpress - OTR

    Milwaukee, WI
    more than 2 months ago
  • $2,200 - $3,100 per week

     ...Requirements ~ CDL Class A ~ Minimum 1 year of verifiable OTR experience ~23 years of age or older ~ HAZMAT Endorsement...  ...dispatchers & Ops Managers are former drivers) ~ Full-Time, steady work ~...  ...Vacancy description Pulse Express invites dry van drivers to... 
    Full time
    Relocation package
    Flexible hours

    Pulse Express

    Milwaukee, WI
    5 days ago
  •  ...OTR Reefer Lease Purchase Drivers: Earn 82% Gross Line Haul & 100% FSC. Join Our Team...  ...business and becoming a truck owner all at the same time....  ...All Automatics ~ OWNER OPERATORS WELCOME! Additional Benefits...  ...Maintenance Program Requirements: Current CDL-A License... 
    For contractors

    Harpers

    Milwaukee, WI
    3 hours ago
  • $7,500 - $10,000 per week

     ...Partnering with Owner Operators CDL-A — Keep 90% of Your Weekly Gross!. Owner Operators CDL-A — Keep 90% of Your Weekly Gross! Looking for consistent freight, strong support, and top earning potential? Join JTS Logistics Inc. and run with a carrier that puts owner-operators... 

    JTS Logistics

    Milwaukee, WI
    2 hours ago
  • $1,800 per week

     ...Carriers is a company operating the Largest Liquid Bulk Chemical Truck Fleet in North...  ...and guidance to our drivers through a network of...  ...Route, & Schedule OTR: Out 2-3 Weeks,...  ...speeding tickets in any motor vehicle at or above...  ...functions required by the driver’s job... 
    Hourly pay
    Weekly pay
    Temporary work
    Live in
    Relocation
    Flexible hours

    Quality Carriers (search conducted by Drive My Way)

    Milwaukee, WI
    a month ago
  • $1,700 - $1,800 per week

     ...CORE48 Transport is hiring experienced OTR CDL-A Drivers who want consistent miles, strong...  ...Freightliner Equipment • Automatic Manual Trucks • 24/7 Driver Support • Pet...  ...Life Insurance + Disability Options REQUIREMENTS • CDL-A Required • 1+ Years Verifiable... 
    Weekly pay
    Flexible hours
    Shift work

    CORE48 Transport

    Wauwatosa, WI
    9 days ago
  • $1,500 - $2,000 per week

     ...,500.00 – $2,000.00 Driver Type: Company Driver...  ...winning, family-owned trucking company located near downtown...  ...This is true OTR with flexible freight...  ...level autonomy , strong operations support, and the ability...  .... There is no requirement such as “X days out =... 
    Weekly pay
    Full time
    Seasonal work
    Flexible hours

    Renewable Transport Services

    Milwaukee, WI
    9 days ago
  • Now Hiring: OTR Truck Drivers for 53' OPEN DECK STEPDECK or 53' Stepteck Conestoga A reputable...  ...to be OTR for 2 - 3 weeks. Requirements: Valid CDL (Commercial Driver’s License...  ...flatbed/stepdeck experience Clean MVR (Motor Vehicle Record) Ability to pass: MVR... 
    Full time
    Immediate start
    Flexible hours

    Good News Trucking Corporation

    Milwaukee, WI
    11 hours ago
  • $100k

     ...RUN OTR (FULL 48 STATES) WITH SAFEWAY LOGISTICS - NO LOCAL POSITIONS...  ...! We are a family-owned, driver-first focused company. We have...  ...name - you are not just a truck number. We have a great driver...  ...Inside cab transforms into an office/dinette Operating Area... 
    Weekly pay
    Work at office
    Local area

    Safeway Logistics

    Milwaukee, WI
    9 days ago
  • $2,200 - $3,100 per week

     ...Requirements ~ CDL Class A ~ Minimum 1 year of verifiable OTR experience ~23 years of age or older ~ HAZMAT Endorsement...  ...dispatchers & Ops Managers are former drivers) ~ Full-Time, steady work ~...  ...Vacancy description Pulse Express prides itself on safe,... 
    Full time
    Relocation package
    Flexible hours

    Pulse Express

    New Berlin, WI
    5 days ago
  • $7,000 - $9,000 per week

     ...Description Job Requirements: 23 years or olderSolid...  ...ExperienceClean Motor Vehicle Record (...  ...Job Description: OTR DRIVERS $1,890.00 PER WEEK63 CENTS PER MILE Owner Ops and Lease...  ...sManual and Automatic trucks spec'd out for...  ...of Benefits: Owner Operators and Company drivers... 
    Weekend work

    Meiborg Bros Inc

    Milwaukee, WI
    10 days ago
  • $55 - $65 per hour

     ...OTR Company Driver - Dry Van TraLo is looking for experienced Class A CDL drivers to join our growing team! As a family-owned and operated company, we take pride in treating our drivers like family...  ...fits your lifestyle. Minimum Requirements: - Class A CDL with 2+... 
    Local area

    TraLo

    Greendale, WI
    5 minutes ago
  • $110k

     ...Join as an Over-The-Road Driver. Haul a mix of Full Truckload and Multi-Stop loads between...  ...cents additional paid on all loads that require Placards. ~ Multi stop with Stop pay...  ...More responsibility deserves more pay. OTR Regional Drivers Welcome to Apply Now →... 
    Weekly pay
    Relocation package
    Flexible hours

    Pinnacle Freight

    Milwaukee, WI
    9 days ago
  • $25 per hour

     ...Requirements ~1 year of CDL-A OTR experience ~ No DUI/DWI in the last 5 years ~ No more than...  ...description Join HMD Trucking as an OTR solo CDL-A Dry Van driver out of Milwaukee, WI to run reliable...  .... What you'll do: Operate late-model company tractors (under... 
    Hourly pay
    Full time
    Second job
    Relocation package
    Flexible hours
    Night shift

    HMD Trucking

    Milwaukee, WI
    5 days ago
  • $15 per hour

     ...Requirements ~1 year of CDL-A OTR experience ~ No DUI/DWI in the last 5 years ~ No more...  ...Vacancy description HMD Trucking is hiring experienced OTR CDL-A drivers in the Milwaukee, WI area to...  ...a supportive, safety-minded operations team. Primary duties: Operate... 
    Hourly pay
    Full time
    Second job
    Relocation package
    Flexible hours
    Night shift

    HMD Trucking

    Milwaukee, WI
    1 day ago
  • $1,800 per week

     ...endorsement or TWIC Card? NO PROBLEM! FlowTrans LLC is hiring OTR and long haul drivers for food-grade freight. No hoses, pumps or hazmat!...  ...in physical condition to perform all essential functions required by the driver’s job description, with or without reasonable... 
    Weekly pay
    Temporary work
    Live in
    Relocation
    Relocation package

    Flowtrans (search conducted by Drive My Way)

    Milwaukee, WI
    more than 2 months ago
  • $70k - $100k

     CDL-A Truck Drivers Class A CDL Drivers – We'll Match You With Carriers Hiring Near You...  ...Regional runs with weekly home time OTR positions with higher mileage pay Dry...  ...depending on the position Minimum Requirements Valid Class A CDL At least 6–12... 
    Local area
    Flexible hours

    JobsTruckDriving.com

    Milwaukee, WI
    2 hours ago
  • $83k

     ...Companies is hiring experienced CDL-A OTR Pro Drivers who are committed to safety,...  ...primarily long-distance freight while operating modern equipment and working with a driver...  ...advancement opportunities Driver Requirements Valid Class A CDL Safe driving... 
    Daily paid
    Long distance

    Wel Companies

    Brookfield, WI
    4 days ago
  • $100k

     ...Description Job Description NEW PAY RATE INCREASE OTR CDL-A Truck Driver Home Weekly | Top Drivers Earn $100,000+ Annually...  ...Card Safe driving record Ability to meet DOT/FMCSA requirements Why MRS? At Midwest Refrigerated Services, we value Modesty... 
    Weekly pay
    Temporary work

    Midwest Refrigerated Milwaukee, Inc.

    Milwaukee, WI
    6 days ago
  • $107.22k

     ...Description Job Description Badger State drivers will find a lot of opportunity with Crete Carrier and Shaffer Trucking. We have weekly home time options on dedicated...  ...out longer can go with our regional or national OTR fleets. Salary: Top 50% average $107,216... 

    Crete Carrier

    Milwaukee, WI
    more than 2 months ago
  • $1,740 per month

     ...Description Job Description Job Requirements: • One Year Verifiable CDL A Experience...  ...Job Description: CDL A W2 OTR Company Truck Drivers | Average Driver Makes $1,740 and...  ...communications and transparency. Our entire operational model has been designed and... 

    JS Helwig and Son LLC

    Milwaukee, WI
    7 days ago
  • $1,900 - $2,400 per week

     ...experienced Class A CDL Solo OTR Truck Drivers for our modern fleet who...  ...time on long-haul nationwide operations. Typical Pay Highlights:...  ...our-team/ . What Makes DSL Express Different: ~ We are a well...  ...Description: Class A CDL required (additional endorsements a plus... 
    Full time
    Seasonal work
    Live in
    Local area
    Flexible hours

    DSL Express

    Milwaukee, WI
    20 days ago
  • $1,400 per week

     ...Description Job Description Job Requirements: •Must Be at Least 23Years...  ...: OUR CDL A REEFER TRUCK DRIVERS EARN UP TO $0.72 CPM - 100K+...  ...dependent on experience and OTR or Regional) •$1,400...  ...Most leather, heated seats. •Owner Operator Spec Perks: •Pet & Rider... 
    Weekly pay
    Temporary work
    Work at office

    Xtreme Trucking, LLC

    Milwaukee, WI
    7 days ago
  • $1,300 - $1,800 per week

    About the job OTR CDL-A TRUCK DRIVERS: $.57 - $.64 CPM Looking for OTR drivers with a valid ClassA License. A minimum of 3 months of verifiable...  ..., PTO, and 401K with matching available after 30 days. Requirements: Experience: Minimum of 3 months experience in the last 3... 

    Cdl A Sense

    Milwaukee, WI
    1 day ago
  • $200k

     ...Soar Transportation is seeking CDL A OTR Reefer Lease Purchase Drivers in the Midwest . Now more than ever...  ...in late model, well-equipped trucks. Compensation ~ Annual pay: $20...  ...full refundable after 12 months Operating ESO - $.08 per mile and cap at $10,0... 
    Hourly pay
    Weekly pay
    For contractors
    3 days per week

    Soar Transportation Group (search conducted by Drive My Way)

    Milwaukee, WI
    more than 2 months ago
  • $29.54 per hour

     ...School Bus Driver – No Exp Needed – Training Provided Join to apply for...  ...mechanics. Responsibilities: Safely operate a school bus on assigned...  ...driving record (no CDL required to start) Must have held a driver...  ..., gender identity, gender expression, genetic information (... 
    Hourly pay
    Weekly pay
    Part time
    Summer work
    Seasonal work
    Local area
    Immediate start
    Monday to Friday
    Flexible hours
    Shift work
    Weekend work
    Day shift

    Durham School Services

    Milwaukee, WI
    3 days ago

Do you want to receive more vacancies?

Subscribe and receive similar vacancies to Truck Driver Owner Operator - 1yr EXP Required - OTR - Bennett Motor Express. Be the first to apply!