ZipRecruiter

Log In

1

Flex Driving Jobs in Wisconsin (NOW HIRING)

GardaWorld

Flex Security Officer

Wauwatosa, WI · On-site

$16 - $18/hr

Ready to suit up as a Special Response/Flex Security Guard? Success in this role depends on ... Valid driver's license required with a clean driving record. Must be able to pass motor vehicle ...

Allied Universal

Security Officer - FLEX

Superior, WI · On-site

$21.05/hr

The Security Professional Branch Flex Officer will serve and safeguard clients across a wide range ... A valid driver's license will be required for driving positions only. Other Related Attributes That ...

GardaWorld

Flex Security Officer

Wauwatosa, WI · On-site

$16 - $18/hr

Ready to suit up as a Special Response/Flex Security Guard? Success in this role depends on ... Valid driver's license required with a clean driving record. Must be able to pass motor vehicle ...

Allied Universal

Security Officer - FLEX

Superior, WI

$21.05/hr

The Security Professional Branch Flex Officer will serve and safeguard clients across a wide range ... A valid driver's license will be required for driving positions only. Other Related Attributes That ...

GardaWorld

Flex Security Officer

Wauwatosa, WI · On-site

$16 - $18/hr

Ready to suit up as a Special Response/Flex Security Guard? Success in this role depends on ... Valid driver's license required with a clean driving record. Must be able to pass motor vehicle ...

Allied Universal

Security Officer - FLEX

Superior, WI · On-site

$21.05/hr

The Security Professional Branch Flex Officer will serve and safeguard clients across a wide range ... A valid driver's license will be required for driving positions only. Other Related Attributes That ...

GardaWorld

Flex Security Officer

Wauwatosa, WI

$16 - $18/hr

Ready to suit up as a Special Response/Flex Security Guard? Success in this role depends on ... Valid driver's license required with a clean driving record. Must be able to pass motor vehicle ...

Prosegur

Flex Officer - Security

Madison, WI · On-site

$16 - $19.25/hr

Flex Officer - Security Duties and responsibilities: * Maintaining a safe and secure environment ... Clean driving record and valid driver license * Capable of following complex instructions * Strong ...

GardaWorld

Flex Security Officer

Wauwatosa, WI · On-site

$16 - $18/hr

Ready to suit up as a Special Response/Flex Security Guard. Success in this role depends on ... Valid driver's license required with a clean driving record Must be able to pass motor vehicle ...

GardaWorld

Flex Security Officer

Wauwatosa, WI · On-site

$16 - $18/hr

Ready to suit up as a Special Response/Flex Security Guard. Success in this role depends on ... Valid driver's license required with a clean driving record Must be able to pass motor vehicle ...

previous pagenext page

Showing results 21-40

All JobsDriving JobsFlex Driving JobsFlex Driving Jobs in Wisconsin

Flex Driving information

See Wisconsin salary details

$6

$20

$40

How much do flex driving jobs pay per hour?

As of Sep 4, 2026, the average hourly pay for flex driving in Wisconsin is $20.81, according to ZipRecruiter salary data. Most workers in this role earn between $16.25 and $22.07 per hour, depending on experience, location, and employer.

What is flex driving?

Flex Driving typically refers to working as a delivery driver for Amazon Flex. Amazon Flex drivers are independent contractors who use their own vehicles to deliver packages to customers. Drivers select delivery blocks through an app and have the flexibility to choose when and how often they work. The job involves picking up packages from Amazon facilities and delivering them to customers within a specified timeframe. It is popular for those seeking a flexible schedule and supplemental income.

What are the key skills and qualifications needed to thrive as a flex driver?

To thrive as a Flex Driver, you need a valid driver's license, a clean driving record, and familiarity with local routes and navigation. Competence with delivery apps, GPS systems, and sometimes basic vehicle maintenance is necessary. Reliability, strong time management, and excellent customer service skills help Flex Drivers stand out. These abilities ensure timely, accurate deliveries and positive customer experiences, which are crucial for repeat business and safety.

What are some common challenges faced by flex drivers and how can they be managed effectively?

Flex Drivers often encounter challenges such as tight delivery deadlines, navigating unfamiliar routes, and managing varying workloads throughout the day. To manage these effectively, it’s important to use reliable navigation apps, plan routes ahead of time, and maintain clear communication with dispatch or customer support when issues arise. Staying organized and keeping a positive attitude can help Flex Drivers adapt to changes and ensure timely deliveries, making the workday smoother and more productive.

What is the difference between Flex Driving vs Delivery Driver?

AspectFlex DrivingDelivery Driver
Required CredentialsValid driver's license, clean driving recordValid driver's license, sometimes specific vehicle certifications
Work EnvironmentFlexible hours, on-demand driving, various locationsScheduled routes, specific delivery areas, often in urban/suburban settings
Employer & Industry UsageGig economy platforms, logistics companiesFood, parcel, or retail delivery services

Flex Driving typically involves on-demand, flexible driving jobs through gig platforms, offering varied hours and locations. Delivery Drivers usually follow scheduled routes for specific delivery services. Both roles require a valid driver's license and are common in the gig and logistics industries, but Flex Driving emphasizes flexibility and on-demand work, while Delivery Drivers focus on scheduled deliveries.

How can I become a flex driver?

To become a Flex driver, you typically need to meet age and driving experience requirements, pass a background check, and have a valid driver's license. You may also need to complete an onboarding process and have access to a smartphone for the app used to accept rides or deliveries.

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

The most popular types of Driving jobs in Wisconsin are:

What are popular job titles related to Flex Driving jobs in Wisconsin?

For Flex Driving jobs in Wisconsin, the most frequently searched job titles are:

What job categories do people searching Flex Driving jobs in Wisconsin look for?

The top searched job categories for Flex Driving jobs in Wisconsin are:

What cities in Wisconsin are hiring for Flex Driving jobs?

Cities in Wisconsin with the most Flex Driving job openings:

Flex Driving jobs near you
Infographic showing various Flex Driving job openings in Wisconsin as of August 2026, with employment types broken down into 1% As Needed, 71% Full Time, 27% Part Time, and 1% Contract. Highlights an 96% Physical, 1% Hybrid, and 3% Remote job distribution, with an average salary of $43,275 per year, or $20.8 per hour.

CDL A Truck Driver - Regional & OTR Flex

Ashley Distribution Services, LTD

Holmen, WI • On-site

$1.6K - $1.9K/wk

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 8 days ago

Job description

Stop Chasing CPM and Get Paid Per Day with Flex Jobs at Ashley Distribution!

If variety keeps you motivated, Ashley’s Flex Driver position is the perfect fit. CDL-A Flex Drivers out of Arcadia, WI run OTR, regional, and local home daily routes, adjusting to business needs. Plus - with daily pay, you can earn a steady income without the stress of chasing miles. Ashley offers 80% company-paid health benefits and industry-low turnover so you know your career is built to last.

Opportunities Open Now for CDL-A Drivers with 1+ Years Experience:

  • Earn $1,625-$1,950 weekly
  • Flexible mix of OTR, regional, and local runs
  • Haul dedicated Ashley freight – consistent and reliable
  • 80% company-paid health insurance - plans as low as $2 per month!
  • Profit sharing, 401(k)
  • Free Wellness Centers
  • Paid weekly + holiday and vacation pay

What sets Ashley apart:

  • Rely on our stability and strength! We operate one of the largest family-owned fleets in the industry.
  • You’re covered for less cost! Ashley covers 27% of the drivers benefits so our CDL-A drivers can enjoy comprehensive healthcare, retirement savings plans, and other valuable benefits at a significantly reduced cost.
  • Share in our success with our generous profit-sharing program!
  • Take care of your health! We offer free Wellness Centers at 3 of our distribution locations.
  • Ashley always has freight to move – whether it’s our own product or other freight – we keep you busy!

Requirements:

  • 21 years or older
  • Valid Class A CDL
  • DOT physical and drug screen
  • Minimum 1 year of recent OTR experience
  • Excellent safety record
  • Stable work history

Ready for a driving job with variety and career stability? Let’s talk about Ashley’s Flex Driver opportunities today.

Benefits:

Eligible employees may participate in our comprehensive benefits package, which may include medical, dental, vision, life, disability, flexible spending accounts, 401(k), paid holidays, paid time off, and applicable state and federal leave benefits. Benefits may vary based on position.

Application Process:

We are accepting applications for this position until it is filled.

Equal Opportunity Employer:

Ashley values diversity and is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status.