Assistant Chief Pilot - Various Aircraft

NTR

VARIOUS VARIOUS AIRCRAFT

Employment - Permanent

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Minimum requirements

Type rating

Not required (Training Provided)

Flight time notes

Commercial or ATP certificate with appropriate ratings for company operations.

License req.

CPL, IR

Open to Lic. Holders

FAA

Medical

Class 2

Visa sponsorship

Not provided

Additional requirements

Strong knowledge of FAA Part 135 regulations and operational requirements
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.
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.

Preferred

Previous experience in pilot leadership, supervision, or pilot development strongly preferred.

Job description

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.