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Contract Pilot Jobs in Wisconsin (NOW HIRING)

WI · On-site

$90 - $120/hr

As an Instructor Pilot at CAE, your role soars beyond training. You are a cultivator of confidence ... contract check airman. * Maintain professionalism and create a welcoming, successful learning ...

WI · On-site

$90 - $130/hr

RAVN provides combat or high maneuver training for pilots, RDT&E, and maintenance services with its ... Manage the assigned contract workload in a fast-growing environment with the core principals in ...

WI · On-site

$70 - $90/hr

Employer Indaver Type contract Permanent What will your working day look like? As R&D pilot operator, you will be responsible for operating, maintaining and optimizing the pilot plant. You take full ...

WI · On-site

$90 - $130/hr

## Global 6500 Instructor Pilot (TCE)Applylocations: Ft Hood, Texastime type: Full timeposted on ... Government contract requirements, only U.S. citizens are eligible for this role.** **Work ...

Stefanini provides the IT contract resources you need to implement crucial projects, handle short ... Work with Pilot Plant Leader to ensure Pilot Plant and business needs are met on an on-going and ...

SANITATION TECHNICIAN

Madison, WI · On-site

$16.75 - $20.25/hr

Stefanini provides the IT contract resources you need to implement crucial projects, handle short ... Work with Pilot Plant Leader to ensure Pilot Plant and business needs are met on an on-going and ...

FIRST OFFICER

Milwaukee, WI · On-site

$97.44/hr

We offer a longevity match with no cap for pilots with 121 experience. Besides competitive pay, Air ... federal contract qualification standards, including those necessary for certification prior to ...

Our commitment to quality has made Palermo's a leader in private label frozen pizza and contract ... Conduct bench-top, pilot plant, and manufacturing trials * Formulate products to meet quality ...

FAA Tutor

Milwaukee, WI · Remote

$18 - $40/hr

... human factors for pilot certification. Ability to explain principles of flight, airspace ... Varsity Tutors does not contract in: Alaska, California, Colorado, Delaware, Hawaii, Maine, New ...

FAA Tutor

Madison, WI · Remote

$18 - $40/hr

... human factors for pilot certification. Ability to explain principles of flight, airspace ... Varsity Tutors does not contract in: Alaska, California, Colorado, Delaware, Hawaii, Maine, New ...

Help validate functional test equipment produced by contract control manufacturers against ... sessions, pilot builds, and reviews of user manuals. * Assist in writing engineering change ...

Help validate functional test equipment produced by contract control manufacturers against ... sessions, pilot builds, and reviews of user manuals. * Assist in writing engineering change ...

Contract (6 Months with Potential Contract-to-Hire) Pay Rate: $58.00 - $64.00 per hour Schedule ... Support prototype builds, pilot production, and manufacturing activities by troubleshooting ...

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Showing results 1-20

Contract Pilot information

See Wisconsin salary details

$50K

$132.1K

$202.9K

How much do contract pilot jobs pay per year?

As of Sep 5, 2026, the average yearly pay for contract pilot in Wisconsin is $132,141.00, according to ZipRecruiter salary data. Most workers in this role earn between $100,900.00 and $156,400.00 per year, depending on experience, location, and employer.

What is a contract pilot?

Contract pilots are professional pilots who are hired on a temporary or per-assignment basis, rather than as full-time employees of an airline or company. They typically operate private jets, corporate aircraft, or charter flights for individuals or organizations that need flight services for a limited period. Contract pilots are responsible for pre-flight planning, operating the aircraft safely, ensuring compliance with aviation regulations, and sometimes handling administrative tasks related to each flight. This flexible arrangement allows both pilots and employers to meet their scheduling and operational needs without long-term commitments.

What does a contract pilot do?

A contract pilot is an aviation professional who operates helicopters, charter planes, or another aircraft on a per-job basis. As a contract pilot, you work directly with corporate or individual clients to fly an aircraft between locations and transport passengers or cargo. Your contract may be for a single trip or multiple trips. However, you operate as an independent contractor, so you are responsible for maintaining your credentials and insurance. Working as a contract pilot provides you with greater flexibility than being a pilot for an airline or the military.

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

To thrive as a Contract Pilot, you need extensive flight experience, an active commercial or airline transport pilot license (CPL/ATPL), and current medical certification. Familiarity with specific aircraft types, proficiency in using advanced avionics systems, and completion of required type ratings are typically necessary. Strong decision-making, adaptability, and effective communication skills help you manage diverse flying environments and coordinate with clients and crews. These competencies ensure safety, regulatory compliance, and reliable service in varied and dynamic aviation assignments.

What are some common challenges faced by contract pilots when adapting to different aircraft and client expectations?

Contract pilots often fly a variety of aircraft types for different clients, which can require quick adaptation to new cockpit layouts, avionics systems, and company-specific procedures. Additionally, each client may have unique operational standards and expectations regarding communication, scheduling, and reporting. Staying organized, maintaining up-to-date certifications, and being proactive in learning new processes are key strategies for overcoming these challenges. Strong interpersonal skills also help contract pilots integrate smoothly with new crews and flight departments.

What is the difference between Contract Pilot vs Commercial Pilot?

AspectContract PilotCommercial Pilot
CertificationsCommercial Pilot Certificate, possibly additional type ratingsCommercial Pilot Certificate, multi-engine ratings often required
Work EnvironmentHired on a temporary basis for specific contracts, often freelanceEmployed by airlines, charter companies, or corporate operators
Employer & Industry UsageContract basis across various operators, including private and cargoFull-time or part-time employment within commercial aviation

Contract pilots typically hold a commercial pilot certificate and work on a temporary or project basis, often flying for multiple operators. Commercial pilots are usually employed full-time by airlines or companies, with a focus on scheduled or charter flights. The main difference lies in employment type and job stability, with contract pilots offering flexibility and diverse opportunities, while commercial pilots often have more consistent employment within the commercial aviation industry.

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

The most popular types of Pilot jobs in Wisconsin are:

What are popular job titles related to Contract Pilot jobs in Wisconsin?

For Contract Pilot jobs in Wisconsin, the most frequently searched job titles are:

What cities in Wisconsin are hiring for Contract Pilot jobs?

Cities in Wisconsin with the most Contract Pilot job openings:

Infographic showing various Contract Pilot job openings in Wisconsin as of August 2026, with employment types broken down into 100% Full Time. Highlights an 75% In-person, and 25% Hybrid job distribution, with an average salary of $132,141 per year, or $63.5 per hour.

Full Time Phenom 100/300 Instructor Pilot (Retention Bonus)

CAE Inc

WI • On-site

$90 - $120/hr

Other

PTO

Posted 4 days ago


CAE rating

8.5

Company rating: 8.5 out of 10

Based on 17 frontline employees who took The Breakroom Quiz

27th of 72 rated aerospace companies


Job description

At CAE, we are all for teaching the next generation. As an Instructor Pilot at CAE, your role soars beyond training. You are a cultivator of confidence and skill, ensuring every pilot you train is fully prepared. Whether you’re leading simulator sessions or pre‑flight briefings, you’ll inspire trust and mastery for the moments that matter. Backed by CAE’s legacy of flight training excellence and a team driven by innovation and collaboration, you’ll have the opportunity to keep your own skills sharp while elevating others. Every day is a chance to take your passion for aviation to new heights, ensuring each lesson meets rigorous regulatory standards and CAE’s unwavering commitment to excellence. With room to grow as an educator, you’ll find purpose and fulfillment in helping pilots excel, no matter the challenges they face.

Description

As an Instructor Pilot at CAE, you will be responsible for delivering high‑quality flight and ground training in accordance with regulatory requirements, CAE‑approved curricula, and customer expectations. Your role goes beyond instruction — you will cultivate pilot confidence and technical mastery through simulator sessions, pre‑ and post‑flight briefings, and a commitment to training excellence.

Key Responsibilities
  • Deliver flight simulator and ground school instruction for assigned aircraft types, supporting type ratings, certificates, internal training, and pilot qualifications.
  • Conduct thorough and professional pre‑ and post‑flight simulator briefings in alignment with CAE standards.
  • Serve as a subject matter expert (SME) and lead clients through their training programs.
  • Complete training records, recommend remedial training when needed, and track instructional qualifications and activity.
  • Support the development of curricula and courseware as an SME when required.
  • After approximately 1.5+ years (subject to business needs), qualify as a Training Center Evaluator (TCE) and customer contract check airman.
  • Maintain professionalism and create a welcoming, successful learning environment.
  • Communicate effectively across all levels, tailoring training methods to a diverse customer base.
  • Ensure accurate and timely documentation aligned with CAE and FAA requirements.
Meet physical demands, including:
  • Frequent climbing of ladders, stairs, ramps, or scaffolding.
  • Occasional work in confined spaces.
  • Prolonged standing or sitting.
  • Occasional movement to complete tasks.
  • Lifting or adjusting objects up to 20 lbs.
Minimum Qualifications
  • Must hold (or meet qualifications to receive) an unrestricted ATP certificate and at least one unrestricted PIC Type Rating.
  • Experience flying single pilot, Part 135 or business aircraft.
  • Strong passion for teaching with effective communication skills.
  • Basic computer proficiency (Microsoft Office and internet‑based applications).
  • Must participate in CAE’s DOT Drug & Alcohol testing program.
  • Must be authorized to live/work in the United States.
  • Ability to meet all physical requirements of the role.
Preferred Qualifications
  • Demonstrated ability to deliver tailored instruction to diverse learners.
  • Strong attention to detail and commitment to high‑quality training delivery.
  • Previous experience developing or contributing to training curricula/courseware.
Benefits
  • Flexible vacation policy and schedule.
  • Paid holidays structured so employees are off between December 25 and January 1.
  • Opportunity to work with cutting‑edge technology and innovative training environments.
  • Freedom to provide customized training (not a scripted program).
  • Ability to remain active in the cockpit while staying close to home.
  • Strong professional growth through collaboration with other pilots.
E‑Verify

As a Federal Contractor, CAE participates in the E‑Verify Program to confirm employment eligibility in the United States. For more information about your rights, please refer to the EEO is the Law poster.

About CAE

At CAE, our mission is clear: to help make the world a safer place. For nearly 80 years, we’ve driven innovation in simulation, training, and mission readiness to support critical operations worldwide. By leveraging advanced technologies, we empower our customers to operate smarter, faster, and more sustainably.

Join a purpose-driven organization where bold ideas are encouraged, collaboration drives progress, and your growth fuels our shared success.

Position Type Regular Equal Opportunity Employer

CAE is an equal opportunity employer committed to providing equal employment opportunities to all applicants and employees without regard to race, color, national origin, age, religion, sex, disability status, protected veteran status, or any other characteristic protected by federal, state or local laws. At CAE, everyone is welcome to contribute to our success. Applicants needing reasonable accommodations should contact their recruiter at any point in the recruitment process. If you need assistance to submit your application because of incompatible assistive technology or a disability, please contact us at CAECarrieres-Careers@cae.com.

Data Privacy

Privacy Statement | CAE As part of our process, we may use AI‑supported tools to help review applications, with human decision‑making at every step.

CAE thanks all applicants for their interest. However, only those whose background and experience match the requirements of the role will be contacted.

Welcome to CAE!

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