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Driving Assistant Jobs in Wisconsin (NOW HIRING)

SP+

Parking Attendant - Driving

Milwaukee, WI

$15.50/hr

Courteously assist Customers by answering any questions they may have. If necessary, direct the ... acceptable driving record. Availability to Work: Special shift requirements, if any, will vary ...

SP+

Parking Attendant - Driving

Milwaukee, WI

$15.50/hr

Courteously assist Customers by answering any questions they may have. If necessary, direct the ... acceptable driving record. Availability to Work: Special shift requirements, if any, will vary ...

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Driving Assistant information

Do you need your license to be a driver helper?

For a driving assistant or driver helper position, having a valid driver's license is typically required since the role involves assisting with vehicle operations and safety. Employers often verify licenses during the hiring process, and good driving records may be preferred. Additional skills such as navigation and communication are also valuable in this role.

What does an assistant driver do?

An assistant driver supports the primary driver by helping with navigation, vehicle maintenance, and ensuring safety during trips. They may also handle tasks such as route planning, maintaining logs, and assisting with passenger needs, often requiring good communication skills and a valid driver's license.

What are the key skills and qualifications needed to thrive as a Driving Assistant, and why are they important?

To thrive as a Driving Assistant, you need a valid driver's license, knowledge of road safety regulations, and basic vehicle maintenance skills. Familiarity with GPS navigation systems, route planning software, and sometimes certifications like defensive driving are typically required. Excellent communication, reliability, and strong organizational skills help you coordinate with passengers and manage schedules effectively. These skills ensure safe, efficient transportation and high-quality service for clients or employers.

Does UPS pay driver helpers weekly?

UPS driver helpers are typically paid weekly, in accordance with standard industry practices for hourly delivery roles. Payment schedules can vary by location and employment terms, so it is advisable to confirm with the local UPS facility or during onboarding.

How can I make extra money by delivering?

Driving assistants can earn extra income by taking on delivery tasks through gig economy platforms or local courier services. This often involves using a personal vehicle, having a valid driver's license, and maintaining good driving records. Flexibility in schedule and familiarity with navigation tools can help maximize earning opportunities.

What is the difference between Driving Assistant vs Delivery Driver?

AspectDriving AssistantDelivery Driver
CredentialsValid driver’s license, possibly some certificationsValid driver’s license, sometimes specialized certifications for certain delivery types
Work EnvironmentAssisting drivers, often in corporate or private settingsDelivering goods to customers, often on a set route
Employer & IndustryLogistics, corporate transportation, or personal servicesCourier services, food delivery, retail logistics

While both roles involve driving, a Driving Assistant primarily supports drivers in various settings, focusing on assisting with vehicle operation and safety. A Delivery Driver, on the other hand, is responsible for transporting goods directly to customers. The roles share similar credentials but differ in work environment and primary responsibilities.

What are some common challenges faced by Driving Assistants, and how can they be overcome?

Driving Assistants often encounter challenges such as adapting to varying traffic conditions, managing tight delivery or pick-up schedules, and ensuring clear communication with both drivers and clients. To overcome these challenges, it's important to stay organized, remain adaptable, and maintain open lines of communication with your team. Familiarity with route planning tools, defensive driving techniques, and customer service best practices can also help Driving Assistants navigate daily demands more effectively.

What are Driving Assistants?

Driving Assistants are professionals who support drivers in various tasks related to transportation. Their responsibilities may include assisting with navigation, helping with loading and unloading cargo, maintaining communication with dispatch, and ensuring that vehicles are clean and safe. Driving Assistants are often employed by delivery companies, logistics firms, or private individuals to improve efficiency and safety during transportation. They may also help with paperwork and compliance with transport regulations. This role is essential for smooth and effective transport operations.
What are the most commonly searched types of Driving jobs in Wisconsin? The most popular types of Driving jobs in Wisconsin are:
What cities in Wisconsin are hiring for Driving Assistant jobs? Cities in Wisconsin with the most Driving Assistant job openings:
Driving Assistant jobs near you
Infographic showing various Driving Assistant job openings in Wisconsin as of July 2026, with employment types broken down into 1% As Needed, 73% Full Time, 23% Part Time, 1% Temporary, and 2% Contract. Highlights an 98% Physical, 1% Hybrid, and 1% Remote job distribution.
Instructional Trainer-Truck Driving

Instructional Trainer-Truck Driving

Waukesha County Technical College

Pewaukee, WI • On-site

$29.17 - $31.50/hr

Full-time, Part-time

Medical, Dental, Life, Retirement, PTO

Posted 13 days ago

Job description

Salary: $29.17 - $31.50 Hourly
Location : WCTC Pewaukee Campus, 800 Main Street, Pewaukee, WI 53072, WI
Job Type: Part Time (21-29 hours/week)
Job Number: 2025-07-16TW
Department: Graphics, Construction, & Transportation
Opening Date: 09/30/2025
Grade/Level: SA7
Description
This position is responsible for driving and related operational skills training for students in the Truck Driving program. This position does not have responsibility for the course, but instead works in open labs to support student learning.
Characteristic Duties and Responsibilities (include, but not limited to)
ESSENTIAL DUTIES AND RESPONSIBILITIES:
  1. Demonstrate and supervise student driving in lab under a variety of environments and driving conditions, including, but not limited to, straight line backing, developing depth perception, making turns, backing into docks and parking places, mirror adjustment, and how to use large mirrors and convex mirrors.
  2. Provide training for students in the truck driving program and students seeking a CDL. This includes administering driving simulations and brake board activities, demonstrating shifting techniques, coupling/uncoupling of semi-trailer combinations, performing vehicle inspection, providing collision avoidance training, and completing scaling activities.
  3. Administer CDL exams
  4. Ensure truck driving equipment is functional and safe. Perform light maintenance on and washing/cleaning of vehicles. Maintain lines on driver training areas. May act as liaison between truck driving program and repair shop. Coordinate purchase of supplies as needed.
  5. Provide assistance in training new instructional assistants
  6. Assist in truck dispatch and use of facility/resources
  7. May assist with program recruitment efforts, such as semi-annual Open Houses events
  8. Other duties as assigned

Minimum Qualifications
REQUIRED KNOWLEDGE, SKILLS, AND ABILITIES:
  • Ability to drive all truck and trailer combinations offered in the truck driving program
  • Ability to plan, organize, and facilitate quality training
  • Ability to work effectively with students, both in one-on-one and group instruction situations
  • Ability to think critically by applying problem solving practices
  • Effective interpersonal communication skills - oral, written, technical and non-technical information, and listening
  • Strong customer service skills, working with individuals from diverse backgrounds
  • Ability to establish and maintain positive working relationships with colleagues
  • Ability to work independently, as part of a team and/or with minimal supervision
  • Basic level of proficiency with computer software applications such as word processing, spreadsheets, databases, presentations and/or publishing.
EDUCATIONAL AND EXPERIENCE REQUIREMENTS:
  • Must possess and maintain a valid Class A Commercial Driver's License (CDL) with air brake endorsement
  • Three years' experience operating large trucks and 48' or 53' trailer required. Seven years strongly preferred.
  • Training and teaching experience in the truck driving industry preferred
  • Experience with van, flatbed, tanker, and doubles preferred
  • In evaluating candidates for this position, the College may consider a combination of education, training, and experience which provides the necessary knowledge, skills, and abilities to perform the duties of the position
  • Employment offer and continued employment is contingent upon negative DOT drug test(s) and acceptable driving record
  • Certified examiner preferred

Supplemental Information
This position supports the Graphics, Construction, and Transportation department and will report to the Associate Dean of Graphics, Construction, and Transportation.
This position requires Wisconsin residence.
This position is part-time, as needed, working up to 24 hrs/week.
The final candidate will have to pass a driving test.
Application detailsAll applicants must submit a completed application along with the following attachments:
1. Current resume (required)
2. A cover letter (optional)
3. Copy of current CDL licensure
Interviews
A final interview date is to be determined.
**Position will be posted until filled**
WCTC provides excellent benefits for our employees. Typical benefits for full-time employees (part-time employee benefits may be prorated) may include:
  • Medical/Dental Insurance
  • Term Life Insurance *
  • Disability Insurance *
  • 403(b) Tax Sheltered Annuity
  • Deferred Compensation
  • Vacation
  • Sick Leave
  • Personal Days
  • Holidays
  • Flexible Spending Accounts
  • Wisconsin Retirement System (if schedule to work at least 1,200 hours per year)
  • Tuition Reimbursement (full-time only)
  • Employee Assistance Program
  • Wellness Activities

* Not available to limited term employees.

Apply