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Flatbed Owner Operator Jobs in Milwaukee, WI (NOW HIRING)

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Flatbed Owner Operator information

See Milwaukee, WI salary details

$274

$5.6K

$6.6K

How much do flatbed owner operator jobs pay per week?

As of Sep 5, 2026, the average weekly pay for flatbed owner operator in Milwaukee, WI is $5,566.48, according to ZipRecruiter salary data. Most workers in this role earn between $4,438.46 and $6,625.00 per week, depending on experience, location, and employer.

What is a flatbed owner operator?

Flatbed Owner Operators are independent truck drivers who own and operate their own flatbed trucks to transport large, heavy, or unusually shaped cargo. Unlike company drivers, they are self-employed and contract with shippers or freight brokers to haul loads. Flatbed Owner Operators are responsible for securing their cargo, maintaining their vehicles, and managing their business operations, including finding loads and handling finances. This job requires specialized knowledge in load securement and compliance with safety regulations. Successful Flatbed Owner Operators often enjoy greater flexibility and earning potential, but also take on more responsibility and risk.

What does a flatbed owner operator do?

A flatbed owner operator has their own commercial vehicle and works on the road as a truck driver hauling various goods throughout the country. As a flatbed owner operator, your primary duties include the safe transport and on-time delivery of products, undamaged. You can haul anything from raw materials like steel and lumber, to construction equipment, vehicles, home goods, frozen foods, and fresh produce. You can be an independent contractor, or work with a larger company that provides truck drivers to their client base. There are part-time, full-time, and seasonal opportunities available. Some employers offer benefits, retirement plans, paid time off, and steady work.

What are the key skills and qualifications needed to thrive as a flatbed owner operator, and why are they important?

To thrive as a Flatbed Owner Operator, you need a valid commercial driver's license (CDL), thorough knowledge of flatbed trucking regulations, and experience with cargo securement and loading. Familiarity with electronic logging devices (ELDs), GPS routing systems, and routine truck maintenance procedures is crucial. Strong time management, problem-solving, and interpersonal skills help build client relationships and ensure timely deliveries. These skills and qualities are vital for safely transporting oversized or irregular loads while maximizing efficiency and profitability.

What are some common challenges flatbed owner operators face while transporting oversized or irregular loads?

Flatbed Owner Operators often deal with oversized or irregular loads that require special handling, securement, and routing. These challenges include ensuring loads are properly secured with appropriate equipment, adhering to state and federal regulations for oversized transport, and coordinating with dispatchers and clients for permits and escorts when necessary. Weather conditions and route restrictions can also impact delivery schedules, so adaptability and strong planning skills are crucial for success in this role.

What is the difference between Flatbed Owner Operator vs Van Owner Operator?

AspectFlatbed Owner OperatorVan Owner Operator
Required CredentialsCommercial Driver's License (CDL), experience with flatbed equipmentCDL optional or standard driver's license, experience with van freight
Work EnvironmentOpen flatbed trailers, loading/unloading with straps and tarpsEnclosed trailers, loading/unloading with pallets and forklifts
Industry UsageConstruction, industrial, and large equipment transportGeneral freight, retail, and e-commerce deliveries

Flatbed Owner Operators typically handle specialized loads requiring securement skills and often work in construction or industrial sectors. Van Owner Operators focus on enclosed freight, suitable for retail and general cargo. Both roles require similar licensing but differ in equipment and work environment, catering to distinct freight types and industry needs.

How do I become an owner operator flatbed?

To become an owner operator flatbed driver, you typically need a valid commercial driver's license (CDL), several years of driving experience, and a clean driving record. You must also secure financing or purchase a suitable flatbed truck and obtain necessary permits and insurance to operate independently in the industry.

Is a flatbed owner operator worth it?

A flatbed owner operator can earn higher pay due to specialized loads and longer hauls, but they also face higher expenses for equipment, maintenance, and insurance. Success depends on managing these costs, securing consistent freight, and maintaining safety standards with skills like load securement. Overall, it can be profitable for experienced operators who handle the business side effectively.

Which flatbed owner operator company pays the most?

In the flatbed owner operator industry, pay rates vary widely depending on factors such as experience, location, and contract terms. Some of the highest-paying companies are known for offering competitive mileage rates, bonuses, and fuel incentives, but specific rankings can change frequently. Owner operators should research individual companies' pay structures and reviews to identify the best-paying opportunities.
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Flatbed Owner Operator jobs near you
Infographic showing various Flatbed Owner Operator job openings in Milwaukee, WI as of August 2026, with employment types broken down into 86% Full Time, and 14% Contract. Highlights an 100% In-person job distribution, with an average salary of $289,457 per year, or $139.2 per hour.

Flatbed Carrier Procurement & Sales

Evans Transportation, Inc

Delafield, WI • On-site

Full-time

Posted 3 days ago

New

Job description

THE POSITION
The Flatbed Carrier Procurement & Sales position is responsible for developing and maintaining a dependable, high-performing flatbed carrier network while delivering consistent service execution across strategic flatbed freight. This role combines flatbed expertise, carrier procurement and sales, relationship management, and strong operational execution to secure reliable capacity and successfully manage freight from load tender through final delivery.
Beyond day-to-day execution, this role will take ownership of strategic flatbed business, proactively identify service and capacity challenges, and drive continuous improvement to help build scalable and reliable flatbed operations.
ROLES AND RESPONSIBILITIES
  • Develop and maintain a dependable, high-performing network of flatbed carriers.
  • Build and strengthen relationships with regional and national flatbed carriers.
  • Source capacity for strategic flatbed and specialized freight opportunities.
  • Leverage knowledge of equipment, securement, and job-site requirements to support successful execution.
  • Identify opportunities for process improvement and operational efficiencies.
  • Support strategic flatbed accounts and dedicated programs as needed.

OPERATIONAL EXCELLENCE
  • Proven ability to manage high-volume freight with exceptional service
  • Strong execution from load tender through delivery -tracking excellence
  • Excellent exception management and problem-solving skills
  • Comfortable making decisions in a fast-paced environment

CARRIER RELATIONSHIP MANAGEMENT
  • Builds long-term partnerships, not just transactional carrier relationships
  • Strong negotiation skills while balancing service, capacity, and cost
  • Ability to strategically grow and develop a reliable carrier network

PROJECT MANAGEMENT MINDSET
  • Highly organized with excellent follow-through
  • Able to manage multiple priorities simultaneously
  • Experience leading operational improvements or special projects
  • Comfortable documenting processes and driving execution across teams

COMMUNICATION & LEADERSHIP
  • Strong communicator with carriers, customers, and internal teams
  • Proactively identifies issues before they become customer problems
  • Collaborative team player who can influence without direct authority
  • High level of accountability and ownership

WHAT SUCCESS LOOKS LIKE
  • Delivers consistent service execution for flatbed customers
  • Develops a dependable, high-performing carrier network
  • Minimizes service failures through proactive planning
  • Drives operational improvements instead of simply maintaining the status quo
  • Can own strategic flatbed accounts with minimal oversight

Requirements
MINIMUM QUALIFICATIONS AND REQUIREMENTS
  • 5+ years of flatbed carrier procurement, carrier sales, or related transportation experience.
  • Deep understanding of flatbed equipment, including Flatbed, Step Deck, Conestoga, RGN, Double Drop, and other specialized equipment.
  • Strong knowledge of freight securement requirements and job-site details.
  • Established relationships within the flatbed carrier market.
  • Strong communication, negotiation, and relationship-building skills.
PREFERRED QUALIFICATIONS AND REQUIREMENTS
  • Background supporting manufacturing, construction, heavy haul, steel, industrial, or other specialized freight customers.
  • Experience with dedicated flatbed programs and/or captive fleets.
  • Established relationships with regional and national flatbed carriers.
  • Experience using project management tools such as Monday.com, Asana, or Microsoft Planner.
  • Demonstrated experience driving process improvements or providing operational leadership.

PHYSICAL AND MENTAL DEMANDS
While performing the duties of this job, the employee must be able to continuously sit, use a keyboard, calculator, and telephone. The employee is occasionally required to stand, walk, stoop, and/or kneel. The employee must occasionally lift and/or move up to 10 pounds while moving files or small packages. Specific vision abilities required by this job include close vision and the ability to adjust focus. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.
The mental and physical requirements described here are representative of those that must be met by an individual to successfully perform the essential functions of this position.
WORK ENVIRONMENT
Work is performed in an office environment. The noise level in the work environment is usually moderate. The work environment characteristics described here are representative of those an individual encounters while performing the essential functions of this position.
The work environment characteristics described here are representative of those an individual encounters while performing the essential functions of this position.

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