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Chief Pilot Jobs in Oregon (NOW HIRING)

Vexcel

Check Airman / Training Pilot

Medford, OR

Coordinate pilot training and instruction events as required in support of the Lead Training Pilot and Chief Pilot. * Recommend improvements to flight training operations. * Performs other related ...

Wimmer Solutions

Blackhawk Pilot

Mcminnville, OR · On-site

$91K - $114K/yr

Perform any other duties during scheduled shift as requested by Aviation Operations Manager (aka Director of Operations) or Chief Pilot (aka Head of flying Operations). * Relocate to Northwest Oregon ...

Vexcel

Check Airman / Training Pilot

Medford, OR · On-site

Coordinate pilot training and instruction events as required in support of the Lead Training Pilot and Chief Pilot. * Recommend improvements to flight training operations. * Performs other related ...

Weyerhaeuser Company

Blackhawk Pilot

Mcminnville, OR · On-site

$108K - $162K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Perform any other duties during scheduled shift as requested by Aviation Operations Manager (aka Director of Operations) or Chief Pilot (aka Head of flying Operations). * Relocate to Northwest Oregon ...

Weyerhaeuser Company

Blackhawk Pilot

Mcminnville, OR · On-site

$108K - $162K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Perform any other duties during scheduled shift as requested by Aviation Operations Manager (aka Director of Operations) or Chief Pilot (aka Head of flying Operations). * Relocate to Northwest Oregon ...

Weyerhauser Co

Blackhawk Pilot

Mcminnville, OR · On-site

$108K - $162K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Perform any other duties during scheduled shift as requested by Aviation Operations Manager (aka Director of Operations) or Chief Pilot (aka Head of flying Operations). * Relocate to Northwest Oregon ...

Weyerhaeuser Company

Blackhawk Pilot

Mcminnville, OR

$108K - $162K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • Retirement

  • PTO

Perform any other duties during scheduled shift as requested by Aviation Operations Manager (aka Director of Operations) or Chief Pilot (aka Head of flying Operations). * Relocate to Northwest Oregon ...

Pilot Company

Assistant General Manager

Aurora, OR · On-site

$69K - $84K/yr

  • Medical

  • Dental

  • Vision

  • Retirement

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

Assistant General Manager

Aurora, OR · On-site

$69K - $84K/yr

  • Medical

  • Dental

  • Vision

  • Retirement

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

Assistant General Manager

Aurora, OR · On-site

$69K - $84K/yr

  • Medical

  • Dental

  • Vision

  • Retirement

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 Oregon

Chief Pilot information

See Oregon salary details

$34.9K

$172.5K

$247.9K

How much do chief pilot jobs pay per year?

As of Aug 19, 2026, the average yearly pay for chief pilot in Oregon is $172,541.00, according to ZipRecruiter salary data. Most workers in this role earn between $129,000.00 and $218,900.00 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 cities in Oregon are hiring for Chief Pilot jobs?

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Chief Pilot jobs near you
Infographic showing various Chief Pilot job openings in Oregon as of August 2026, with employment types broken down into 67% Full Time, and 33% Part Time. Highlights an 67% In-person, and 33% Remote job distribution, with an average salary of $172,541 per year, or $83 per hour.

Check Airman / Training Pilot

Vexcel

Medford, OR

Full-time

Re-posted 8 days ago

Job description

Vexcel Aerial Imagery is looking for a Check Airman/Training Pilot. This position assists in the development and verification of our commercial pilots in the safe operation of single and multi-engine aircraft. This role requires an experienced pilot with good interpersonal skills who enjoys working with and educating our commercial pilots.

The Check Airman is responsible for ensuring that company pilots can safely operate our high performance single and multi-engine aircraft in complex airspace and ever changing weather. Along with the rest of the training team the Check Airman duties are to annually verify that every Vexcel pilot is competently and safely able to operate Vexcel?s fleet of aircraft. This person will be responsible for providing simulator and aircraft checkouts in our wide range of aircraft, which includes Cessna 206?s and 210?s, Piper Aztecs & Navajo?s, Cessna 310?s and other models. As Check Airman, you will be a key component in ensuring Vexcel maintains a safe and productive working environment through initial and recurrent training.

DUTIES AND RESPONSIBILITIES:

  • Achieve expert level knowledge of all aircraft and systems used by Vexcel and deliver initial and recurrent training to the pilots in each aircraft they are authorized to operate.
  • Utilize a flight simulator to evaluate and verify pilot skills and ensure pilots are fully capable of handling known emergency situations.
  • Perform ?in aircraft? skill verification and provide local & cross-country skill training for pilots in the type aircraft they are being checked in.
  • Ensure pilots are safely operating aircraft in compliance with all laws and regulations of the Federal Aviation Administration.
  • Document all training in the company databases along with maintaining and updating training materials in the company database.
  • Coordinate pilot training and instruction events as required in support of the Lead Training Pilot and Chief Pilot.
  • Recommend improvements to flight training operations.
  • Performs other related duties as assigned by management.

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