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Aviation Chief Pilot Jobs (NOW HIRING)

Tradewind

Southeast Regional Chief Pilot

Oxford, CT · On-site

About Tradewind Tradewind Aviation is a leading Part 135 commuter and on-demand private charter ... Base Chief Pilots will work closely with the Chief Pilot and company leadership to support day-to ...

Pacifico Energy Group

Chief Pilot

Titusville, FL · On-site

The Chief Pilot will play a key role in ensuring the safe and effective operation of our fleet across military and general aviation environments, including DCMA, Part 91, and Part 135 flight ...

LifeFlight of Maine

Assistant Chief Pilot

Bangor, ME · On-site

TheACPis afull-timesalaried aviation positioncomprisedofmanagement requirements,concurrent ... The Assistant Chief Pilot will maintain all qualifications of an LFAS Captain. Duties include ...

Wing

Assistant Chief Pilot

Dallas, TX · On-site

... for aviation and the ongoing development of this new industry. This position is subject to Wing ... What You'll Do: * Assist the Chief Pilot to oversee the safe and compliant daily operation of Wing ...

Rio Staffing

Regional Chief Pilot

White Plains, NY

$160K - $180K/yr

Regional Chief Pilot - Northeast Base Location: Westchester County Airport (KHPN) - White Plains, N ... Designed perfectly for a pilot transitioning into long-term aviation management. This is 95% in ...

Premier Private Jets

Chief Pilot

Stuart, FL · On-site

About Us Premier Private Jets is a distinguished provider of comprehensive business aviation ... The Chief Pilot is responsible for the leadership, standardization, regulatory compliance, training ...

Questec

Chief Pilot (Req #: 145)

Columbia, MO

$130K - $150K/yr

This is a unique opportunity to establish and shape the aviation function within our organization from the ground up. The Chief Pilot will be responsible for all aspects of flight operations ...

Questec

Chief Pilot (Req #: 145)

Columbia, MO

$130K - $150K/yr

This is a unique opportunity to establish and shape the aviation function within our organization from the ground up. The Chief Pilot will be responsible for all aspects of flight operations ...

Questec

Chief Pilot (Req #: 145)

Columbia, MO

$130K - $150K/yr

This is a unique opportunity to establish and shape the aviation function within our organization from the ground up. The Chief Pilot will be responsible for all aspects of flight operations ...

Kalitta Air, LLC

Assistant Chief Pilot

Ypsilanti, MI · On-site

Assistant Chief Pilot Department: Flight Operations Reports To : Chief Pilot POSITION PURPOSE ... Associates or Bachelor's degree in Aviation Management or a related field preferred. * Previous ...

Lowe's

Chief Pilot

Charlotte, NC

Your Impact The Chief Pilot (CP) will bring and maintain a strong track record in aviation that includes a focus on safety and successful management of the pilot workforce. The CP will provide day-to ...

PACCAR

Chief Pilot, Seattle 1

Seatac, WA

Privately owned aviation support has been a part of PACCAR business for decades. Our 18-person team ... Our Chief Pilot at the Seattle base is retiring at the end of May 2026. We would like to identify a ...

W3Global Inc.

Chief Pilot Part 135 (Remote)

Lima, NY · On-site +1

$160K - $180K/yr

The ideal candidate is a proven aviation leader with strong Part 135 operational experience ... Serve as the designated Chief Pilot for Part 135 operations. * Lead, mentor, and support a ...

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Aviation Chief Pilot information

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$33K

$163.2K

$234.5K

How much do aviation chief pilot jobs pay per year?

As of Jun 17, 2026, the average yearly pay for aviation chief pilot in the United States is $163,193.00, according to ZipRecruiter salary data. Most workers in this role earn between $122,000.00 and $207,000.00 per year, depending on experience, location, and employer.

How much do chief pilots earn?

Chief pilots typically earn between $80,000 and $200,000 annually, depending on factors such as airline size, experience, and location. They are responsible for overseeing flight operations, ensuring safety standards, and managing flight crews, often requiring extensive flight hours and certifications.

Is Angelina Jolie a licensed pilot?

Angelina Jolie is not known to be a licensed pilot. For aviation chief pilots, obtaining a commercial pilot license and relevant certifications is essential, but there is no public record indicating Jolie holds such licenses.

What pilots make $500,000 a year?

Chief pilots or senior airline captains with extensive experience, especially those flying large, long-haul international aircraft for major airlines, can earn annual salaries of $500,000 or more. These high earnings typically result from years of experience, additional certifications, and flying high-demand routes, often supplemented by bonuses and profit-sharing. Such compensation is more common among top-tier airline pilots rather than entry-level or regional pilots.

How much money does a chief pilot make?

A chief pilot's salary varies based on experience, airline size, and location, but typically ranges from $80,000 to over $200,000 annually. They oversee flight operations, ensure safety compliance, and often hold advanced certifications such as an Airline Transport Pilot (ATP) license.

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

To thrive as an Aviation Chief Pilot, you need extensive flight experience, an Airline Transport Pilot (ATP) certificate, strong leadership abilities, and thorough knowledge of aviation regulations. Familiarity with advanced flight management systems, scheduling software, and safety management systems (SMS) is typically required. Outstanding communication, decision-making, and organizational skills help Chief Pilots lead crews and coordinate operations effectively. These competencies ensure safe flight operations, regulatory compliance, and efficient team management within an aviation organization.

What are some common challenges Aviation Chief Pilots face in managing flight operations and crew members?

Aviation Chief Pilots often navigate challenges such as coordinating complex flight schedules, ensuring compliance with evolving aviation regulations, and maintaining high safety standards across all operations. They are responsible for mentoring and evaluating pilots, which requires strong leadership and communication skills. Additionally, Chief Pilots regularly collaborate with other departments, such as maintenance and dispatch, to address operational issues and ensure efficient, safe flights. Balancing administrative duties with supporting flight crews in a dynamic environment is a key aspect of the role.

What are the responsibilities of an Aviation Chief Pilot?

An Aviation Chief Pilot is responsible for overseeing the flight operations of an airline or aviation department. This includes managing pilot staff, ensuring regulatory compliance, developing flight policies, and coordinating with maintenance and safety teams. The Chief Pilot also plays a key role in hiring, training, and evaluating pilots, while serving as the main liaison between flight crews and upper management. Their leadership ensures safe, efficient, and reliable flight operations.
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Aviation Chief Pilot jobs near you
Infographic showing various Aviation Chief Pilot job openings in the United States as of June 2026, with employment types broken down into 95% Full Time, and 5% Part Time. Highlights an 89% Physical, 3% Hybrid, and 8% Remote job distribution, with an average salary of $163,193 per year, or $78.5 per hour.
Southeast Regional Chief Pilot

Southeast Regional Chief Pilot

Tradewind

Oxford, CT • On-site

Full-time

Posted 18 days ago

Job description

Description:

About Tradewind

Tradewind Aviation is a leading Part 135 commuter and on-demand private charter operator with operational bases at the Waterbury/Oxford, CT (OXC), Westchester, NY (HPN), Stuart, FL (SUA) and San Juan, PR (SJU) airports. Founded by aviation enthusiasts in 2001 on the premise that all flights deserve the highest quality aircraft, crew, and service, Tradewind provides personal air travel—both private and scheduled service—throughout North America and the Caribbean.

For more details visit www.flytradewind.com

About the Role / Candidate

Tradewind Aviation is seeking dedicated and experienced Regional Chief Pilots to support our Northeast (HPN), Southeast (SUA) and Caribbean (SJU) operations. This role is designed for a proactive aviation leader who thrives in a dynamic environment and is committed to safety, operational excellence, and pilot support.


Base Chief Pilots will work closely with the Chief Pilot and company leadership to support day-to-day flight operations, oversee pilot activity in their assigned region, and ensure compliance with FAA regulations, company policies, and Tradewind’s safety culture.


This is primarily an in-office role, with limited flying responsibilities.

Requirements:


Essential Functions

  • Pilot leadership & oversight
  • Provide direct supervision, guidance, and support to flight crewmembers assigned to the region.
  • Address operational, performance, and safety concerns in a timely and professional manner.
  • Ensure pilots adhere to established company procedures, regulatory requirements, and safety standards.
  • Serve as an accessible leadership presence for pilots, promoting a positive and transparent culture.

Operational Support & Compliance

  • Support the Chief Pilot in maintaining compliance with FAA regulations, company manuals, and all operational standards.
  • Assist in maintaining operational control and facilitating communication between flight crews, Dispatch, and leadership.
  • Monitor crew qualifications, scheduling requirements, and readiness for assigned missions for trip executed in the assigned region.
  • Ensure adherence to the General Operations Manual and other company guidance.

Training & Checking

  • Conduct pilot evaluation, ground and flight training, base-level standardization, and recurrent/proficiency activities as assigned.
  • Support the Director of Operations and Director of Training in evaluating and enhancing training programs.
  • Maintain knowledge of current aviation regulations, company policy changes, and industry best practices, ensuring timely dissemination of relevant updates to flight crews.

Administration & Base Management

  • Serve as the primary liaison for region-specific pilot issues, operational needs, and personnel support.
  • Assist with performance evaluations, coaching, documentation, and follow-up actions.
  • Participate in pilot recruiting, interviewing, and onboarding activities for the assigned region.
  • Coordinate initiatives, pilot meetings, and local operational improvements.

Cross-Functional Collaboration

  • Collaborate closely with the Chief Pilot, SVP of Operations, Director of Operations, Director of Training, and Safety Department to align region activities with company goals.
  • Support safety investigations, corrective action plans, and proactive safety initiatives.

Flying & Operational Duties

  • Perform limited line flying as required, including missions supporting training, checking, and operational continuity.
  • Maintain personal qualifications and currency in accordance with company policies and FAA requirements.

Other Duties

  • Carry out additional assignments as assigned by the Chief Pilot

QUALIFICATIONS

  • Commercial or ATP certificate with appropriate ratings for company operations.
  • Strong knowledge of FAA Part 135 regulations and operational requirements.
  • Previous experience in pilot leadership, supervision, or pilot development strongly preferred.
  • Excellent communication, interpersonal, and problem-solving skills.
  • Ability to work flexibly, support on-call operational needs, and travel occasionally.
  • Demonstrated commitment to safety, professionalism, and high operational standards.

Apply