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Chief Pilot Jobs in Wisconsin (NOW HIRING)

PHI Health, LLC

WI · On-site

$80 - $120/hr

Job Summary Under the general direction of the Chief Pilot, Manager, Training and the auspices of the FAA, ensure pilots are qualified under applicable regulations and company policies by ...

RAVN Group, Inc

WI · On-site

$120 - $180/hr

Chief Pilot. * Director of Flight Operations. * Program Manager. * Site Lead. * Business Development Director. * Operations Executive. * Vice President or other executive leadership roles. Physical ...

New

Imh

Instructor / Check Airman

Waukesha, WI · On-site

$51.11 - $80.45/hr

Collaborates with the Chief Pilot to address training needs and operational improvements. * Serves as a mentor to pilots, promoting professional growth and development. * Participates in safety ...

New

Oshkosh Corporation, Inc.

Captain

Oshkosh, WI · On-site

$118.60 - $204/hr

Complete all required Company, Department, Regulatory, and Aircraft specific training at the specified intervals. Assist Chief Pilot and/or Director of Aviation with requested tasks outside of flight ...

Oshkosh Corporation

Captain

Oshkosh, WI · On-site

Complete all required Company, Department, Regulatory, and Aircraft specific training at the specified intervals. * Assist Chief Pilot and/or Director of Aviation with requested tasks outside of ...

Oshkosh Corporation

Captain

Oshkosh, WI · On-site

Complete all required Company, Department, Regulatory, and Aircraft specific training at the specified intervals. * Assist Chief Pilot and/or Director of Aviation with requested tasks outside of ...

Pilot Company

Retail Merchandiser

Beloit, WI · On-site

$16.50 - $24.87/hr

Company Description Pilot Company is an industry-leading network of travel centers with more than ... Haslam II and currently led by CEO Adam Wright, our founding values, people-first culture and ...

Pilot Company

Retail Merchandiser

Beloit, WI · On-site

$16.50 - $24.87/hr

Company Description Pilot Company is an industry-leading network of travel centers with more than ... Haslam II and currently led by CEO Adam Wright, our founding values, people-first culture and ...

Pilot Company

Retail Merchandiser

Beloit, WI

$16.50 - $24.87/hr

Company Description Pilot Company is an industry-leading network of travel centers with more than ... Haslam II and currently led by CEO Adam Wright, our founding values, people-first culture and ...

Pilot Company

Retail Merchandiser

Beloit, WI

$16.50 - $24.87/hr

Company Description Pilot Company is an industry-leading network of travel centers with more than ... Haslam II and currently led by CEO Adam Wright, our founding values, people-first culture and ...

Pilot Company

Retail Merchandiser

Beloit, WI

$16.50 - $24.87/hr

Company Description Pilot Company is an industry-leading network of travel centers with more than ... Haslam II and currently led by CEO Adam Wright, our founding values, people-first culture and ...

Ellsworth

Chief Technology Officer

Germantown, WI · Hybrid

Establish mechanisms to pilot, test, and scale new digital initiatives, ensuring disciplined ... Demonstrated success serving as a CTO, CIO, or senior technology advisor , including or interim ...

Pilot Flying J

Retail Merchandiser

Beloit, WI · On-site

$16.50 - $24.87/hr

Company Description Pilot Company is an industry-leading network of travel centers with more than ... Haslam II and currently led by CEO Adam Wright, our founding values, people-first culture and ...

Pilot Company

Food Services Leader

Franksville, WI · On-site

$15.70 - $23.33/hr

Company Description Pilot Company is an industry-leading network of travel centers with more than ... Haslam II and currently led by CEO Adam Wright, our founding values, people-first culture and ...

Pilot Company

Deli Shift Leader I

Oak Creek, WI · On-site

$14.95 - $22.22/hr

Company Description Pilot Company is an industry-leading network of travel centers with more than ... Haslam II and currently led by CEO Adam Wright, our founding values, people-first culture and ...

Pilot Company

Guest Services Leader

Franksville, WI · On-site

$15.70 - $23.33/hr

Company Description Pilot Company is an industry-leading network of travel centers with more than ... Haslam II and currently led by CEO Adam Wright, our founding values, people-first culture and ...

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Showing results 1-20

All JobsChief Pilot JobsChief Pilot Jobs in Wisconsin

Chief Pilot information

See Wisconsin salary details

$33.3K

$164.7K

$236.7K

How much do chief pilot jobs pay per year?

As of Sep 4, 2026, the average yearly pay for chief pilot in Wisconsin is $164,719.00, according to ZipRecruiter salary data. Most workers in this role earn between $123,100.00 and $208,900.00 per year, depending on experience, location, and employer.

What is a chief pilot?

A chief pilot manages the daily operations of an aviation department for an airline. As a chief pilot, your job is to oversee all pilots, ground personnel, and flight attendants. Your duties involve scheduling flights, coordinating aircraft maintenance, and ensuring the department meets all local and federal regulations. Some chief pilots monitor all day-to-day logistics for their department. This career requires a bachelor’s degree in aviation or a similar discipline. Additional qualifications include between 2,000 and 5,000 hours of flight time, current FAA certification, and excellent management skills.

What are some common challenges faced by chief pilots in managing flight operations teams?

Chief Pilots often navigate the challenge of balancing administrative responsibilities with supporting flight crews and ensuring regulatory compliance. They must address scheduling complexities, manage crew resource needs, and adapt to changing aviation regulations. Additionally, fostering open communication and a strong safety culture among pilots is crucial, as is providing mentorship and training to support professional development within the team.

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

To thrive as a Chief Pilot, you need an Airline Transport Pilot (ATP) certificate, extensive flight experience, in-depth knowledge of aviation regulations, and strong leadership abilities. Familiarity with flight management systems, safety management systems (SMS), and crew scheduling software is typically required. Exceptional decision-making, communication, and organizational skills are essential to lead flight crews and ensure regulatory compliance. These skills and qualifications are critical for maintaining operational safety, regulatory adherence, and effective team leadership within an aviation organization.

How much does a chief pilot get paid?

A chief pilot's salary typically ranges from $80,000 to $150,000 annually, depending on the airline, experience, and location. They are responsible for overseeing flight operations, ensuring safety standards, and managing pilot staff, often requiring advanced certifications and extensive flight hours.

What does a chief pilot do?

A chief pilot oversees flight operations, ensuring safety, compliance, and efficiency within an airline or aviation organization. They manage flight crews, develop policies, and coordinate training, often holding certifications such as an Airline Transport Pilot license. The role requires strong leadership, communication skills, and knowledge of aviation regulations.
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What are popular job titles related to Chief Pilot jobs in WI?

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Chief Pilot jobs near you
Infographic showing various Chief Pilot job openings in Wisconsin as of August 2026, with employment types broken down into 2% Internship, 1% As Needed, 86% Full Time, 10% Part Time, and 1% Contract. Highlights an 91% Physical, 2% Hybrid, and 7% Remote job distribution, with an average salary of $164,719 per year, or $79.2 per hour.

IFR Check Airman

PHI Health, LLC

WI • On-site

$80 - $120/hr

Other

Re-posted 8 hours ago

Job description

Job Summary

Under the general direction of the Chief Pilot, Manager, Training and the auspices of the FAA, ensure pilots are qualified under applicable regulations and company policies by administering line checks and proficiency checks as directed. Instruct company pilots and medical crews as directed.

Responsibilities
  • Evaluate the performance and knowledge of rotor wing pilots in accordance with FAA regulations and company policies through pilot proficiency checks as directed.
  • Provide flight and ground instruction.
  • Assist the Chief Pilot in reviewing and updating the pilot training curriculum.
  • Assist in creating necessary flight documents as required by the training department.
  • Maintain compliance with Department of Health and OSHA rules as they apply to the Air Medical Department.
  • Support company Safety Management System activities.
  • Comply with company HS&E policies and procedures.
  • Promote PHI's Destination Zero initiative at the line level.
  • Maintain currency.
  • Perform any other duties as assigned.
Qualifications
  • Hold a First Class Medical.
  • Have a minimum of two years prior experience as an FAA‑designed Check Airman.
  • Meet CAMTS qualifications for PIC rotor wing:
    • 2,000 total flight hours
    • 1,500 hours helicopter
    • 1,000 hours PIC helicopter
    • 500 hours turbine helicopter
    • 100 hours unaided night operations or 50 hours unaided and 100 hours night‑vision goggle (NVG)
    • 75 hours instrument (actual & hood)
  • Preference for Airline Transport Pilot license.
  • Preference for experience in EC135 & BH407.
  • Pass a pre‑placement physical exam including functional capacity exam (strength and flexibility assessment, lift 100 lbs), drug screening, and background screen.
  • Meet and maintain the company’s flight personnel weight restriction policy (individual weight ≤ 235 lbs).
  • Communicate verbally, effectively, and clearly in person and by radio.
Schedule / Location

7‑7 shift in Burleson, TX.

Compensation & Benefits

Competitive pay and benefits package including a sign‑on bonus up to $50,000.

Disclaimer

The above statements are intended to describe the general nature and level of work being performed by people assigned to this classification. They are not intended to be construed as an exhaustive list of all responsibilities, duties, and skills required of personnel in this classification.

Equal Employment Opportunity Statement

PHI, Inc. provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.

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