Owner operator driver jobs in Milwaukee, WisconsinCreate job alerts

Position Description Immediate Opening! We Can Accommodate Automatic Restrictions and have an opening for a SOLO Class A CDL Truck Driver in Milwaukee, WI We will buy your truck! If you’re looking to switch from Owner Operator to Company Driver, we can help make the switch even easier! Call or Text "Milwaukee" to Shaunna at 904-541-9566 See and Hear from a Ryder Employee who Drives for Us Here: Youmight be wondering what your paycheck will look like. $1600 or more per week - And it gets better • Driver Positions Pay Weekly, • Weekly Guarantee $1600 per week, • Travel required within WI. Will be gone for a week or more at a time. Will stay in hotel., • Tractor Trailer and Flatbed experience needed, • Hours Per Week: 50 + hours per week, • Hourly Pay: $30.90 Per Hour, • Per Diem Pay: $50.00 per night, • Tenure Bonus: Pays You $300 Four Times A Year, Every Quarter, • Loyalty Bonus: Pays you $2500 at 6 months and $2500 at 1 year., • Schedule: Monday – Friday/Sunday - Thursday Trucks are three years or newer. Ryder Drivers Service the Route, not the Truck. All Drivers have 24/7 Roadside Maintenance by a Ryder Trained Technician plus Service Employees fuel up our trucks at all 800+ Maintenance Facilities. • Deliver SOLO To: WI, • Route: Regional, • Tractor Type: Day Cab, • Trailer Type: 28', 48' & 53 Flatbed Call or Text "Milwaukee" to Shaunna at 904-541-9566 EXTRA PERKS: Our Drivers tell us Carrier Transparency is top priority. Don’t spend time applying for jobs with ‘Average Pay’ or confusing pay structures. We know you’re essential to keep our economy afloat. Your trust, safety and security is our top priority. You will work with the Safest and most Reliable Fleet in the Industry. You Deliver for us so we make sure to Deliver for you! We have all the benefits other carriers do without the wait! • Paid Time Off Starts at Day 1- 80 hours accrued in 1st year, • Medical, Dental, Vision Start at 30 Days, • We love our Ryder babies and offer 12 weeks of PAID Maternity Leave for qualifying employees (eligibility requirements, including work tenure, apply), • Immediate 401k rollover and contributions with company match at one year, • HIGH VALUED Stock at 15% Employee Discount, • UNIFORMS, CELL PHONE AND BOOT ALLOWANCE PROVIDED, • Ryder Drivers are the Captain of the Ship – we trust and support OUR DRIVERS to make decisions to keep yourself and others safe We have always had stringent cleaning processes and will provide personal protective equipment to keep you safe as you keep America moving! Still looking? Check out our site all Driving Opportunities with Ryder EEO/AA/Female/Minority/Disabled/Veteran Requirements • Minimum 21 years of age, • Pass a Ryder Drug Test, • Pass a Ryder Background and Motor vehicle check including Drug and alcohol verification from previous employers for the last 3 years, • Pass a DOT physical, • Pass a Ryder road test, • Provide appropriate CDL and endorsements for the position, • Must have Class A verifiable experience in a tractor trailer or comparable vehicle:, • 9 months experience within the past 3 years, OR, • 2 years’ experience within the last 5 years, OR, • 5 years’ experience within the last 10 years, • Ability to follow written and/or oral instructions Responsibilities • Ensuring compliance with applicable federal and/or state laws, regulations, and/or agency rules, standards and guidelines, • Detecting and eliminating or minimizing safety hazards Maintaining accurate records and logs, • Loading/Unloading freight or assisting in the loading/unloading of freight if required by customer Posted Date 21 hours ago (12/10/2025 10:28 PM) Requisition ID 2025-192811 Primary State/Province WI Primary City Milwaukee Location (Posting Location) : Postal Code 53221 Category Drivers Regional/OTR Solo Employment Type Regular-Full time Travel Requirements Driver Position Code 1000599

Pioneer is Now Hiring CDL-A Flatbed Company Drivers! \nEarn Up to $90,000 per Year - $5,000 Sign-On Bonus \nMostly Home Weekly - Full Healthcare Benefits \n\n Top Company Driver Benefits: \n\n\n\t • Top drivers earn up to $90,000 per year\n\t, • Average $1,500-$1,800 weekly gross pay\n\t, • Average $1,200-$1,500 weekly net pay\n\t, • Home weekly or bi-weekly\n\t\n\t\t, • We strive to get our drivers home on weekends\n\t\n\t\n\t, • $5,000 sign-on bonus\n\t, • $3,000 referral bonus\n\t, • Detention pay\n\t, • Direct Deposit, paid out every Friday\n\t, • Full benefits with BCBS - eligible 1st day of the month after 31 days of employment\n\t, • Lease Operators average $4,000-$5,000 per week*\n\t, • Home weekends\n\t, • $5,000 sign-on bonus\n\t, • $3,000 referral bonus\n\t, • All expenses paid orientation\n\t, • 77% of line haul for Tractor and Trailer\n\t, • 100% of fuel surcharge paid to owner\n\t, • STEP ONE: Request info by submitting this form\n\t, • STEP TWO: Complete the Pioneer application (provided upon completion of STEP ONE and takes 10-15 min)\n\t, • Newer equipment - 2021-2025 Freightliners and International's\n\t, • Holiday pay eligible after 180 days of employment\n\t, • Single dispatcher for each driver\n\t, • Free rider & pet programs\n\t, • Valid Class A CDL\n\t

Currently Hiring Company Truck Drivers (CDL-A Only).Apply today and within 24 hours you'll receive multiple job offers. Earn $.60 - $.80+ CPM! and up per year based on position. Simply select the driving job that offers you what is most important.Higher pay, increased benefits or more home-time: You choose.Avg. Company Driver Job Offers Salary: $85,000-$110,000+Avg. Owner Operator Job Offers Salary: $200,000-$325,000+ Apply now to receive your job offers!Pandologic. Category: , Keywords: Truck Driver

Dedicated Regional CDL-A Truck Driver Jobs Available Now.Apply today and within 24 hours you'll receive multiple job offers. Earn $.60 - $.80+ CPM! and up per year based on position. Simply select the driving job that offers you what is most important.Higher pay, increased benefits or more home-time: You choose.Avg. Company Driver Job Offers Salary: $85,000-$110,000+Avg. Owner Operator Job Offers Salary: $200,000-$325,000+ Apply now to receive your job offers!Pandologic. Category: , Keywords: Class A Driver

CDL-A Owner Operator Jobs | Independent Contractor Opportunities REAL Security. REAL Freight. REAL Pay. Driver with Confidence. Partner with Freymiller. Are you aCDL-A Owner OperatororIndependent Contractorlooking for: • Steady miles, • High-paying freight, • Weekly pay NEW Pay Raise Just Dropped! • Up to 70% Line Haul Revenue, • Fuel Surcharge - Ask Us How, • Big Sign-On Compensation!, • We Cover Travel to Orientation, • Paid Drop Pick-Up, • Weekly Settlements = Fast Cash Flow, • Huge Fuel Discounts (Best in the Industry) Don't just drive- partner up. Apply Today and see what's possible with Freymiller!

Job Description CDL-A DRIVERS: FIND THE JOB RIGHT FOR YOU $60,000 - $120,000+ | COMPANY, LEASE, AND OWNER OPERATOR POSITIONS Are you looking for a driving job that fits your life-not the other way around? Whether you're a new CDL-A holder or a seasoned owner-operator, I can help you find your best route. As a former truck driver, I understand what drivers really want. I work for you, not just the company. WHAT'S AVAILABLE: ● Company Drivers | Lease Operators | Owner Operators ● Regional, OTR, and Dedicated Routes ● CDL-A Required (OK if you need training - we've got you covered) PAY & BENEFITS: ● $60K - $120K+ annually based on experience and type of trucking ● Full Benefits Package: Medical, Dental, Vision, Paid Time Off ● 401(k) with Company Match ● Weekly Pay & Direct Deposit ● Paid Orientation & Training Programs ● Late-Model Equipment & 24/7 Driver Support HOME TIME THAT WORKS FOR YOU Flexible scheduling based on your availability and area. LET ME HELP YOU FIND YOUR FOREVER JOB. Contact: Tonia Baudoin 601-688-4141 Job Posted by ApplicantPro

Average revenue range: $180,000-$250,000 • With Schneider FreightPower, owner-operators gain significantly more access to Schneider’s diverse range of freight: Choose from all the traditional loads available to owner-operators and other freight Schneider manages., • Options to pick from:, • All-In Revenue: Select loads with an all-in rate – no need to calculate fuel or accessorials., • Percent of Revenue: Select loads with 65% of linehaul revenue and 100% of fuel surcharge and accessorial at load completion., • Self-dispatch: Pick your loads, home time, lanes and revenue., • Haul dry van trailers with 90% drop-and-hook freight at no charge while operating under Schneider’s authority., • Get $456 on your second settlement payment and $252 each week for the next 22 weeks, for a total of $6,000 in incentives (terms and conditions apply)., • Possess a valid Class A Commercial Driver’s License., • Minimum 6 months of Class A driving experience., • Meet the following tractor requirements:, • Truck(s) must be 2011 or newer., • Truck(s) need to pass a DOT inspection., • Engine(s) must meet EPA10 emissions requirements., • Truck(s) need a functioning Collision Mitigation System., • Compensation for time spent in orientation., • Discounts on fuel, tires, maintenance and more through ___, • Tools to help you succeed: Doing business with Schneider means being provided a Samsung tablet you can use inside and outside your cab and having free trailer usage., • Access to company facilities: Take full advantage of Schneider’s facilities, which provide free parking, free laundry, meal options, exercise equipment and more. Compensation details: 180000-250000 Yearly Salary PIe77e817c615e-37820-38411880

Job Description🚛 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.

Job DescriptionOwner Operator Benefits and Requirements: • No-touch freight, • Detention and tarp pay, • 100% fuel surcharge pass-through, • Furnished fuel card, • Pickup/drop pay, • No hold back time on settlements, • No upfront cost to sign-on, • Owner-operator percentage pay, • No trailer rent or hidden fees on trailers, • Must have a CDL A, • Must be at least 22 years of age, • At least 1 year of OTR experience in the last 3 years, • 3 max total accidents and moving violations in the last 3 years, • No DUI's DWI's in the past 3 years, • Trucks must be 1998 or newer, • CSA points reviewedLease-Purchase Benefits and Requirements:, • $2,000 sign-on bonus, • $250 gift card when you leave with your first load, • 2016 and newer equipment: Freightliner, Volvo and Peterbilts, • Late-model/new trucks, • Reasonable payments and terms, • No money down, • Weekly settlements, • Vast fuel discounts, • Tire and maintenance programs, • Business partner support (ATBS), • No forced dispatch, • Specialized training, • Must have a CDL A, • Must be at least 22 years of age, • At least 1 year of OTR experience in the last 3 years, • 3 max total accidents and moving violations in the last 3 years, • No DUI's DWI's in the past 3 years, • CSA points reviewed

Job DescriptionOwner Operator Benefits and Requirements: • No-touch freight, • Detention and tarp pay, • 100% fuel surcharge pass-through, • Furnished fuel card, • Pickup/drop pay, • No hold back time on settlements, • No upfront cost to sign-on, • Owner-operator percentage pay, • No trailer rent or hidden fees on trailers, • Must have a CDL A, • Must be at least 22 years of age, • At least 1 year of OTR experience in the last 3 years, • 3 max total accidents and moving violations in the last 3 years, • No DUI's DWI's in the past 3 years, • Trucks must be 1998 or newer, • CSA points reviewedLease-Purchase Benefits and Requirements:, • $2,000 sign-on bonus, • $250 gift card when you leave with your first load, • 2016 and newer equipment: Freightliner, Volvo and Peterbilts, • Late-model/new trucks, • Reasonable payments and terms, • No money down, • Weekly settlements, • Vast fuel discounts, • Tire and maintenance programs, • Business partner support (ATBS), • No forced dispatch, • Specialized training, • Must have a CDL A, • Must be at least 22 years of age, • At least 1 year of OTR experience in the last 3 years, • 3 max total accidents and moving violations in the last 3 years, • No DUI's DWI's in the past 3 years, • CSA points reviewed