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Instructor Pilot Jobs in Wisconsin (NOW HIRING)

NV5

Assistant Chief Pilot

Sheboygan Falls, WI · On-site +1

Overview NV5 is seeking an Assistant Chief Pilot to support the Director of Flight Operations by ... Certified Flight Instructor. CFI, CFII, and MEI. * Live within a 90-mile radius of the following ...

NV5

Assistant Chief Pilot

Sheboygan Falls, WI · On-site

NV5 is seeking an Assistant Chief Pilot to support the Director of Flight Operations by reinforcing ... Certified Flight Instructor. CFI, CFII, and MEI. * Live within a 90-mile radius of the following ...

Green County

Patrol Deputy Full-time

Monroe, WI · On-site

$61K/yr

... Instructor, Bilingual (Spanish), and SWAT Team Leader. Several benefit time options: vacation ... Drone Pilot, and Crisis Negotiator. Incentive pay for physical readiness. Lateral Transfer:

Green County, WI

Patrol Deputy Full-time

Monroe, WI · On-site

$61K/yr

... Instructor, Bilingual (Spanish), and SWAT Team Leader. Several benefit time options: vacation ... Drone Pilot, and Crisis Negotiator. Incentive pay for physical readiness. Lateral Transfer:

Dodge County

Deputy Sheriff

Juneau, WI · On-site

$36.10 - $40.62/hr

Detective, K9, SWAT, Crash Investigation Team, Rec Patrol, Civil Process, Drug Task Force, Drone Pilot, DRE, Unified Tactics Instructors, Honor Guard, Field Training Officer, Supervisor positions ...

Dodge Company

Deputy Sheriff

Juneau, WI · On-site

$36.10 - $40.62/hr

Detective, K9, SWAT, Crash Investigation Team, Rec Patrol, Civil Process, Drug Task Force, Drone Pilot, DRE, Unified Tactics Instructors, Honor Guard, Field Training Officer, Supervisor positions ...

COUNTY OF DODGE

Deputy Sheriff

Juneau, WI · On-site

$36.10 - $40.62/hr

Detective, K9, SWAT, Crash Investigation Team, Rec Patrol, Civil Process, Drug Task Force, Drone Pilot, DRE, Unified Tactics Instructors, Honor Guard, Field Training Officer, Supervisor positions ...

All JobsInstructor Pilot JobsInstructor Pilot Jobs in Wisconsin

Instructor Pilot information

See Wisconsin salary details

$39.9K

$104K

$173.1K

How much do instructor pilot jobs pay per year?

As of Jun 16, 2026, the average yearly pay for instructor pilot in Wisconsin is $104,002.00, according to ZipRecruiter salary data. Most workers in this role earn between $84,800.00 and $127,700.00 per year, depending on experience, location, and employer.

What is the difference between Instructor Pilot vs Flight Instructor?

AspectInstructor PilotFlight Instructor
CertificationsCommercial Pilot Certificate, Certified Flight Instructor (CFI) often requiredCertified Flight Instructor (CFI) required
Work EnvironmentMilitary, corporate, or government aircraft trainingFlight schools, general aviation
Employer & IndustryAirlines, military, government agenciesFlight training schools, private aviation

Instructor Pilot and Flight Instructor both require CFI certification, but Instructor Pilots often operate in military or corporate settings, focusing on advanced training. Flight Instructors typically work in civilian flight schools, training new pilots. While their roles overlap in training and certification, Instructor Pilots usually handle more complex aircraft and scenarios, whereas Flight Instructors focus on foundational pilot training.

What Does a Pilot Instructor Do?

Pilot Instructors teach students how to fly so that they can obtain their pilot’s licenses. This position takes patience, precision, a sense of detail, and cool thinking under pressure. You will teach your student each and every step involved in flight. This often begins with classroom instruction and may later involve such actions as filing a flight plan, completing a pre-flight checklist, radio communication with ground personnel, and all details of takeoff, navigation, and landing. Eventually, you will guide your students through test flights. You will then file reports to your leadership on the progress of your students and help decide who is qualified to obtain their pilot’s licenses.

What are Instructor Pilots?

Instructor Pilots are highly trained and experienced pilots who are responsible for teaching student pilots how to operate aircraft safely and effectively. They provide both ground and flight instruction, evaluate student performance, and ensure adherence to aviation regulations. Instructor Pilots may work in flight schools, military settings, or commercial training programs, and are essential for developing the next generation of competent aviators. Their role includes demonstrating maneuvers, providing feedback, and preparing students for exams and certifications.

What are some common challenges Instructor Pilots face when training new pilots, and how can they be addressed?

Instructor Pilots often encounter challenges such as varying learning speeds among students, managing cockpit safety during training flights, and providing constructive feedback under pressure. To address these, it's important to tailor teaching methods to individual student needs, maintain clear communication and situational awareness at all times, and foster a supportive learning environment. Regular collaboration with other instructors and ongoing professional development also help Instructor Pilots stay updated on best practices and regulatory changes.

What are the key skills and qualifications needed to thrive as an Instructor Pilot, and why are they important?

To thrive as an Instructor Pilot, you need advanced piloting skills, a commercial or airline transport pilot certificate, and a certified flight instructor (CFI) rating. Familiarity with flight simulators, aircraft-specific avionics, and training management systems is typically required. Strong communication, patience, and the ability to give constructive feedback are vital soft skills for effectively teaching and mentoring student pilots. These skills ensure safe flight operations, effective knowledge transfer, and the development of competent new pilots.
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Instructor Pilot jobs near you
Infographic showing various Instructor Pilot job openings in Wisconsin as of June 2026, with employment types broken down into 1% As Needed, 50% Full Time, 47% Part Time, 1% Temporary, and 1% Contract. Highlights an 89% Physical, 3% Hybrid, and 8% Remote job distribution, with an average salary of $104,002 per year, or $50 per hour.
Pilot Proficiency Center Instructor Pilot

Pilot Proficiency Center Instructor Pilot

Experimental Aircraft Association, Inc.

Oshkosh, WI • On-site

Part-time

Posted 13 days ago

Job description

Are you interested in collaborating with passionate people?
Experimental Aircraft Association (EAA) is a community of passionate aviation enthusiasts, and the only association of its kind to offer the fun and camaraderie of sharing the love of flying, building, and restoring recreational aircraft. Our vision is to expand an already vibrant and growing aviation community. EAA hosts the AirVenture Fly-In annually at Wittman Regional Airport in Oshkosh, Wisconsin. This event is EAA's annual convention and draws more than 650,000 attendees and 10,000 aircraft.
EAA is a sought-after organization with a competitive and unique benefit package, which includes the EAA Flying Club, career advancement opportunities, fun perks, along with being immersed around passionate EAA Members and Volunteers.
SUMMARY
Provide flight and ground instruction following FAA regulations, Airmen's Information Manual, Advisory Circulars, airport operations, and Experimental Aircraft Association (EAA) policies, procedures, and curriculum. Ensure that each student meets course standards, training requirements, and objectives. We want to create and further encourage safe, competent, and proficient pilots.
We are adding to our pool of flight instructors. This is a part-time position needed in Oshkosh, WI, to help cover instructional needs on weekends, occasional nights and during the summer.
ROLES AND RESPONSIBILITIES
  1. Complete all Ground and Flight activities according to the EAA Training Course Curriculum.
  2. Perform those flight instructor duties authorized by the Federal Aviation Regulations following the approved Training Course Curriculum.
  3. Responsible for accurately maintaining all appropriate records, including student training records, student logbook, computer records, and all appropriate endorsements.
  4. Ensure that all assigned students meet course standards, training requirements and objectives.
  5. Monitor maintenance condition of the training aircraft, and inform EAA maintenance personnel of any questionable items.
  6. Provide flight and ground instruction to enrolled students while maintaining the highest level of safety and standards.
  7. Maintain a clean, professional environment - both in the aircraft and on the EAA grounds.
  8. Embraces and supports the EAA mission and performs safe practices in the workplace and aviation environment.
  9. All other duties as assigned.

MINIMUM QUALIFICATIONS
  • Certified Flight Instructor - Airplane (CFI) required; medical not required
  • Knowledge of appropriate Federal Aviation Regulations and related administrative and operational procedures and requirements
  • Knowledge of an ability to apply an effective instructional technique in the classroom and on the flight deck
  • Ability to work well under pressure in a fast-paced environment while exercising sound judgment at all times

PREFERRED QUALIFICATIONS
  • Currently enrolled in an undergraduate or post-undergraduate degree program or holding a bachelor's degree is preferred
  • Actively instructing
  • Light Sport Aircraft flight training experience
  • Minimum of 100 hours of dual instruction given

PHYSICAL REQUIREMENTS
Typical office setting. Exerting up to 10 pounds of force occasionally, and/or a negligible amount of force frequently or constantly to lift, carry, push, pull or otherwise move objects, including the human body. Sedentary work involves sitting most of the time. Jobs are sedentary if walking and standing are required only occasionally, and all other sedentary criteria are met.
Preparation for AirVenture or other events may require lifting up to 50 lbs occasionally, standing and walking for extended periods of time while bending, squatting, kneeling, twisting, and push and pull motions.
All offers of employment are contingent upon successfully passing a pre-employment drug screen and background check. EAA offers a comprehensive benefits package to all full-time positions.
EAA is an Equal Opportunity Employer. This company will provide equal opportunity to all individuals without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status. Information collected regarding categories as provided by law will in no way affect the decision regarding an employment application.
Equal Opportunity Employer
This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights notice from the Department of Labor.

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