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Seasonal Owner Operator Jobs in Wisconsin (NOW HIRING)

On-site Staffing Services

Be Seen First

Dishwasher

Madison, WI · On-site

$18/hr

Dishwasher (Seasonal) - Madison, WI On-Site Staffing Services is currently accepting applications ... owned and operated employment placement agency taking a hands-on approach to creating a skilled ...

Sentry Insurance

Seasonal Housekeeper

Stevens Point, WI · On-site

$16/hr

The team is seeking a Seasonal Part-Time housekeeper to join our detail-oriented housekeeping team ... SentryWorld is owned and operated by Sentry Services, an affiliate of Sentry. Who You'll Want to ...

Sentryinsurance

Seasonal Housekeeper

Stevens Point, WI

$16/hr

The team is seeking a Seasonal Part-Time housekeeper to join our detail-oriented housekeeping team ... SentryWorld is owned and operated by Sentry Services, an affiliate of Sentry. Who You'll Want to ...

Sentry

Seasonal Housekeeper

Stevens Point, WI · On-site

$16/hr

The team is seeking a Seasonal Part-Time housekeeper to join our detail-oriented housekeeping team ... SentryWorld is owned and operated by Sentry Services, an affiliate of Sentry. Who You'll Want to ...

Quad

Forklift Seasonal

Lomira, WI

$18.75 - $22/hr

The Seasonal Production forklift workers assist in meeting production goals and deadlines during ... like owners and to take charge of their own success. Whether an operator, sales rep, a graphic ...

Quad

Forklift Seasonal

Hartford, WI

$18.50 - $21.75/hr

The Seasonal Production forklift workers assist in meeting production goals and deadlines during ... like owners and to take charge of their own success. Whether an operator, sales rep, a graphic ...

VS Ripp Trucking LLC

Dump Truck Driver

Dane, WI · On-site

$20.25 - $26.50/hr

... our family owned & operated business. Canidate must have: A valid CDL-A or CDL-B Manual or ... Work is seasonal (mid-May thru Thanksgiving - generally)

Quad

Forklift Seasonal

Hartford, WI · On-site

$18.50 - $21.75/hr

... like owners and to take charge of their own success. Whether an operator, sales rep, a graphic ... The Seasonal Production forklift workers assist in meeting production goals and deadlines during ...

On-site Staffing Services

Be Seen First

Seasonal Food Service

Milwaukee, WI · On-site

$18.40/hr

Company Description On-Site Staffing Services is a family owned and operated employment placement agency taking a hands-on approach to creating a skilled workforce in the greater Milwaukee area. As a ...

Quad

Forklift Seasonal

Lomira, WI · On-site

$18.75 - $22/hr

... like owners and to take charge of their own success. Whether an operator, sales rep, a graphic ... The Seasonal Production forklift workers assist in meeting production goals and deadlines during ...

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All JobsOwner Operator JobsSeasonal Owner Operator JobsSeasonal Owner Operator Jobs in Wisconsin

Seasonal Owner Operator information

What is a seasonal owner operator?

A Seasonal Owner Operator is an independent contractor who owns and operates their own commercial vehicle, typically working for a specific period during peak seasons such as holidays or harvest times. These professionals often transport goods or provide specialized services for companies that experience increased demand during certain times of the year. Seasonal Owner Operators are responsible for maintaining their vehicles, managing schedules, and ensuring timely deliveries. This role offers flexibility and higher earning potential during busy periods but may also involve variable workloads and income throughout the year.

What are the key skills and qualifications needed to thrive as a seasonal owner operator?

To thrive as a Seasonal Owner Operator, you need a valid commercial driver's license (CDL), experience in logistics or trucking, and a strong understanding of vehicle maintenance. Familiarity with GPS navigation, electronic logging devices (ELDs), and basic freight management software is typically required. Excellent time management, customer service, and problem-solving skills help you adapt to seasonal fluctuations and customer demands. These competencies ensure safe, efficient, and reliable operations during peak periods when demand for transportation services is highest.

What are some common challenges faced by seasonal owner operators, and how can they be managed effectively?

Seasonal Owner Operators often encounter challenges such as fluctuating demand, tight delivery schedules, and variable weather conditions that can impact routes and timelines. Managing these challenges requires strong time management, proactive vehicle maintenance, and adaptability to changing workloads. Building good relationships with dispatchers and clients can also help secure consistent assignments throughout the season. Planning ahead and networking within the industry can make the seasonal workflow smoother and more rewarding.

What is the difference between Seasonal Owner Operator vs Truck Driver?

AspectSeasonal Owner OperatorTruck Driver
CredentialsCommercial Driver's License (CDL), business registrationCDL, possibly additional endorsements
Work EnvironmentOperate own truck, flexible schedule, seasonal routesCompany-owned trucks, fixed routes, year-round
Employer & IndustryIndependent, contracted with carriers, trucking industryEmployers or fleet operators, trucking industry

Seasonal Owner Operators typically own their trucks, work independently, and operate on seasonal schedules, offering flexibility but bearing more responsibilities. Truck Drivers usually work for a company, operate company-owned trucks, and have more consistent schedules. Both roles require a CDL and are integral to the trucking industry, but differ mainly in ownership, independence, and seasonal versus year-round work.

What are the most commonly searched types of Owner Operator jobs in Wisconsin?

The most popular types of Owner Operator jobs in Wisconsin are:

What cities in Wisconsin are hiring for Seasonal Owner Operator jobs?

Cities in Wisconsin with the most Seasonal Owner Operator job openings:

Seasonal Owner Operator jobs near you
Infographic showing various Seasonal Owner Operator job openings in Wisconsin as of August 2026, with employment types broken down into 51% Full Time, 47% Part Time, 1% Contract, and 1% Nights. Highlights an 99% Physical, and 1% Remote job distribution.

Seasonal Lawn Care & Mowing Technician - 22 per Hour

Lawn Doctor

Wales, WI • On-site

$22/hr

Full-time

Posted 7 days ago

Lawn Doctor rating

6.7

Company rating: 6.7 out of 10

Based on 36 frontline employees who took The Breakroom Quiz

17th of 36 rated gardening and landscaping

Job description

Benefits:
  • Flexible schedule
  • Free uniforms
  • Opportunity for advancement
  • Training & development

Lawn Doctor is hiring dependable seasonal help through the fall, with the potential to transition into full-time, year-round employment.
Job responsibilities:
  • Residential and commercial lawn mowing
  • fertilization and weed control
  • Core aeration
  • Fall leaf and yard cleanups
  • Operating and maintaining professional lawn equipment
  • Driving company vehicles and trailers between job sites

Requirements:
  • Valid driver's license and a good driving record
  • Dependable, punctual, and able to work independently
  • Comfortable performing physical outdoor work
  • Able to lift 50 pounds and work in varying weather conditions
  • Lawn care or equipment experience is preferred, but we're willing to train the right person

Pay: $22 per hour
Schedule: Seasonal employment through the fall, with the potential for full-time, year-round work
Compensation: $22.00 - $22.00 per hour
Our Franchisees Need People Like You
Here at Lawn Doctor, we have a very simple approach to our work-be safe, have fun, and change the world one lawn at a time. It's the kind of approach that, not surprisingly, has led us to the highest customer satisfaction and retention rates in the industry.
Lawn Doctor locations across the country offer phenomenal employment opportunities.* Whether you're an experienced technician or just starting out on your career path, all you need is a passion for success and a strong work ethic to be a candidate to join your local Lawn Doctor franchise. No matter the task, our independent operators know that every Lawn Doctor employee plays an important role in providing customers with the great results they expect, while making the local community a little happier. Your work will never go unappreciated.
Since each of our franchises is locally owned, you'll get to work for and with people in your area and become part of a close-knit Lawn Doctor family. If you enjoy working outdoors, being largely self-directed with little supervision, and would like a chance to help make the world a greener place, we would love to talk to you.
We appreciate your interest and hope to have you on board a local franchise team as soon as possible.
* All Lawn Doctor locations are independently owned and operated. All positions identified here are positions offered by individual Lawn Doctor franchisees.

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