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Local Owner Operator Truck Driver Jobs in Reedsburg, WI

Heartland Express

Regional CDL-A Truck Driver

Portage, WI · On-site

$55K - $92K/yr

Paid orientation & training * 48 state operating area * Scheduled wage increases annually * Latest ... Our trucks run 68 MPH * Paid vacation * Health, dental, vision, & life insurance * Detention pay ...

Heartland Express

Regional CDL-A Truck Driver

Baraboo, WI · On-site

$55K - $92K/yr

Paid orientation & training * 48 state operating area * Scheduled wage increases annually * Latest ... Our trucks run 68 MPH * Paid vacation * Health, dental, vision, & life insurance * Detention pay ...

Sysco

CDL B Local Delivery Truck Driver

Baraboo, WI · On-site

$29.60 - $33.10/hr

... Local Delivery Truck Job Summary: All drivers run daily routes with frequent stops and are required to load packages onto hand trucks and unload product at each stop on the assigned route in the ...

Asian Foods

CDL A Delivery Truck Driver

Baraboo, WI · On-site

$110K/yr

Outstanding benefits - www.syscobenefits.com Excellent full time career with a stable and growing company JOB SUMMARY Sysco has immediate job openings for dependable local CDL A Delivery Truck ...

Asian Foods

CDL A Delivery Truck Driver

Baraboo, WI

$10 - $48/hr

Excellent full time career with a stable and growing company JOB SUMMARY Sysco has immediate job openings for dependable local CDL A Delivery Truck Drivers to safely and efficiently operate a tractor ...

Asian Foods

CDL A Delivery Truck Driver

Baraboo, WI · On-site

$110K/yr

Outstanding benefits - www.syscobenefits.com Excellent full time career with a stable and growing company JOB SUMMARY Sysco has immediate job openings for dependable local CDL A Delivery Truck ...

Asian Foods

CDL A Delivery Truck Driver

Baraboo, WI · On-site

$110K/yr

Excellent full time career with a stable and growing company JOB SUMMARY Sysco has immediate job openings for dependable local CDL A Delivery Truck Drivers to safely and efficiently operate a tractor ...

Asian Foods

CDL A Delivery Truck Driver

Baraboo, WI · On-site

$110K/yr

Outstanding benefits - www.syscobenefits.com Excellent full time career with a stable and growing company JOB SUMMARY Sysco has immediate job openings for dependable local CDL A Delivery Truck ...

Asian Foods

CDL A Delivery Truck Driver

Baraboo, WI

$110K/yr

Outstanding benefits - www.syscobenefits.com Excellent full time career with a stable and growing company JOB SUMMARY Sysco has immediate job openings for dependable local CDL A Delivery Truck ...

Walsh Cargo Inc

OTR Driver

Lyndon Station, WI · On-site

$1.3K - $1.4K/wk

We are looking for a company driver or an owner operator to run customer reefer freight from ... Company Description Family owned trucking company that hauls customer reefer freight from Wisconsin ...

Uber

Driver

Wilton, WI

... local truck driver, company truck driver, taxi driver, taxi chauffeur, cab driver, cab chauffeur, taxi cab driver, transit bus driver, bus driver, coach bus driver, bus operator, shuttle driver, bus ...

Uber

Driver

Kendall, WI

... local truck driver, company truck driver, taxi driver, taxi chauffeur, cab driver, cab chauffeur, taxi cab driver, transit bus driver, bus driver, coach bus driver, bus operator, shuttle driver, bus ...

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All JobsLocal Owner Operator Truck Driver JobsLocal Owner Operator Truck Driver Jobs in Reedsburg, WI

Local Owner Operator Truck Driver information

See Reedsburg, WI salary details

$193

$2.1K

$4.4K

How much do local owner operator truck driver jobs pay per week?

As of Aug 17, 2026, the average weekly pay for local owner operator truck driver in Reedsburg, WI is $2,134.21, according to ZipRecruiter salary data. Most workers in this role earn between $1,057.69 and $3,909.62 per week, depending on experience, location, and employer.

What is a local owner operator truck driver?

Local Owner Operator Truck Drivers are independent contractors who own or lease their own trucks and operate them within a specific geographic area, usually within a single city or region. Unlike company drivers, they manage their own business operations, decide their schedules, and are responsible for maintenance and expenses. These drivers typically handle pick-ups and deliveries that allow them to return home daily or nightly. Local routes provide more consistent home time compared to long-haul trucking, making the role appealing for those seeking work-life balance.

What does a local owner operator truck driver do?

A local owner-operator truck driver transports cargo around the region in which they operate. In this position, you own or lease your truck, and you work on an independent basis with different clients. Your duties include maintaining your vehicle, building relationships with clients, and locating new contract opportunities. When you have a contract, you plan the route and delivery schedule, if necessary. On some jobs, you load and unload the cargo at pick-up and delivery points, but many clients have their own warehouse workers. As a local driver, your transportation responsibilities focus on one area, so you do not usually take multi-day trips.

What are the key skills and qualifications needed to thrive as a local owner operator truck driver?

To thrive as a Local Owner Operator Truck Driver, you need a valid commercial driver's license (CDL), a clean driving record, and knowledge of local and state transportation regulations. Familiarity with GPS navigation systems, electronic logging devices (ELDs), and basic vehicle maintenance tools is typically required. Strong time management, customer service, and problem-solving abilities help drivers excel in meeting delivery schedules and handling unexpected challenges. These skills ensure safe, efficient, and reliable transportation of goods, which is crucial for customer satisfaction and business success.

What are some common challenges faced by local owner operator truck drivers, and how can they be managed?

Local owner operator truck drivers often encounter challenges such as managing their own schedules, balancing time on the road with maintenance needs, and handling administrative tasks like invoicing and compliance paperwork. Additionally, because they own their truck, they are responsible for all upkeep, repairs, and insurance, which can impact profitability if not carefully managed. Building strong relationships with local clients and staying organized with routes and paperwork can help mitigate these challenges, ensuring more consistent work and smoother operations.

What is the difference between Local Owner Operator Truck Driver vs Local Company Driver?

AspectLocal Owner Operator Truck DriverLocal Company Driver
CredentialsCommercial Driver's License (CDL), business licensesCommercial Driver's License (CDL)
Work EnvironmentOwn truck, independent, flexible scheduleCompany vehicle, supervised, fixed schedule
Employer & Industry UsageOwns business, contracts with carriersEmployed by a trucking company
Search & Comparison IntentOwnership, independence, earnings potentialEmployment, benefits, stability

In summary, Local Owner Operator Truck Drivers own and operate their trucks, offering flexibility and potential earnings, while Local Company Drivers work for a trucking company with a fixed schedule and benefits. The choice depends on your desire for independence versus employment stability.

How much do local owner operator truck drivers make?

Local owner operator truck drivers typically earn between $150,000 and $250,000 annually, depending on factors such as experience, routes, and freight type. They are responsible for managing their own schedules, expenses, and equipment, which can impact overall earnings.
More about Local Owner Operator Truck Driver jobs

What cities near Reedsburg, WI are hiring for Local Owner Operator Truck Driver jobs?

Cities near Reedsburg, WI with the most Local Owner Operator Truck Driver job openings:

Local Owner Operator Truck Driver jobs near you
Infographic showing various Local Owner Operator Truck Driver job openings in Reedsburg, WI as of August 2026, with employment types broken down into 96% Full Time, and 4% Part Time. Highlights an 100% In-person job distribution, with an average salary of $110,979 per year, or $53.4 per hour.

CDL A Local Delivery Truck Driver - Up to $5000 Sign On Bonus

Sysco

Baraboo, WI • On-site

Full-time

Medical, Retirement, PTO

Re-posted 9 days ago

Sysco rating

7.6

Company rating: 7.6 out of 10

Based on 321 frontline employees who took The Breakroom Quiz

120th of 364 rated logistics

Job description

Company:

US0018 Sysco Baraboo, LLC

Sales Territory:

None

Zip Code:

53913

Travel Percentage:

0

COMPENSATION INFORMATION:

The pay range provided is not indicative of Sysco's actual pay range but is merely algorithmic and provided for generalized comparison. Factors that may be used to determine rate of pay include specific skills, work location, work experience and other individualized factors

Click on the hyperlink to watch A Day in the Life of a Sysco Driver.

More than the road: Start your delivery partner career with Sysco TODAY!

****** Up to $5,000 Sign On Bonus ********

Earn Up To $105,000/Per Year!

Positions also available in Deforest, Plover, Wausau, Janesville, Platteville, Minocqua, Glidden, Rice Lake, Eau Claire, Freeport and more!

Job Summary:

Sysco has immediate job openings for dependable local CDL A Delivery Truck Driver to safely and efficiently operate a tractor-trailer and manually unload/deliver various products (meats, produce, frozen foods, groceries, dry goods, supplies, etc.) to customer locations on an assigned route schedule. Our truck drivers build relationships with each customer using their positive, friendly attitude and become familiar with their operations to meet needs and expectations.

QUALIFICATIONS
Minimum Requirements

  • 21+ years of age.

  • Pass employment testing

  • License to drive - valid Class A Commercial Driver License (CDL) with a driving record that meets company insurability standards

  • Commercial Vehicle Drivers must have the ability to read and speak the English language sufficiently to converse with the general public, to understand highway traffic signs and signals in the English language, to respond to official inquiries, and to make entries on reports and records.

  • Touch freight - may need to lift, push or move product weighing an average of 40-60 pounds and as much as 100 pounds repeatedly.

  • Flexibility - overtime as required, weekends and holidays as business needs require.

Preferred Requirements

  • 1 year customer delivery experience preferred.

  • 6 months hand cart/hand truck experience preferred.

  • 6 months Food and Beverage experience preferred.

  • 2 years consistent work history preferred.


BENEFITS

  • Excellent pay, including productivity incentives.

  • Most Driver Trainees have daily routes and are home nightly.

  • Paid vacation and holidays.

  • Ongoing job skills and leadership development training.

  • Career growth opportunities - we promote from within!

  • New hires are eligible first day of the month following or coinciding with 31 days from date of hire.

  • Comprehensive healthcare benefits.

  • Generous retirement benefits.

  • Employee discount programs.

  • Service recognition and employee rewards.

  • Discounts on Sysco stock (SYY).

  • Referral programs.

  • Safety programs.

  • Tuition reimbursement.

  • Uniforms.

  • More benefits, too many to name.


Sysco is more than just a place to work. Our passion for food and our customers has made us the industry leader. To remain on top, we will continue to think bigger, work harder and never give up. It takes a special kind of CDL A Delivery Truck Driver to work for Sysco. Are you ready to drive success?


Click on the hyperlink to watch A Day in the Life of a Sysco Driver.

BENEFITS INFORMATION:

For information on Sysco's Benefits, please visit https://SyscoBenefits.com

OVERVIEW:

Sysco is the global leader in foodservice distribution. With over 71,000 colleagues and a fleet of over 13,000 vehicles, Sysco operates approximately 333 distribution facilities worldwide and serves more than 700,000 customer locations.

We offer our colleagues the opportunity to grow personally and professionally, to contribute to the success of a dynamic organization, and to serve others in a manner that exceeds their expectations. We're looking for talented, hard-working individuals to join our team. Come grow with us and let us show you why Sysco is at the heart of food and service.

AFFIRMATIVE ACTION STATEMENT:

Applicants must be currently authorized to work in the United States.

We are proud to be an Equal Opportunity and Affirmative Action employer, and consider qualified applicants without regard to race, color, creed, religion, ancestry, national origin, sex, sexual orientation, gender identity, age, disability, veteran status or any other protected factor under federal, state or local law.

This opportunityis available through Sysco Corporation, its subsidiaries and affiliates.

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