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Tradewind Aviation

HPN Base Assistant Chief Pilot

Yonkers, NY, USA|Travel, Onsite

Job Overview

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Employment Type

Full-time
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Compensation

Type:
Salary
Rate:
Range $75,300.00 - $185,900.00
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Work Schedule

Flexible
On-call
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Benefits

Health Insurance
Dental Insurance
Retirement Plan
Paid Time Off
Professional development programs
travel benefits
Flexible working hours

Job Description

Tradewind Aviation is a premier Part 135 commuter and on-demand private charter operator known for its commitment to delivering high-quality personal air travel experiences. Established by aviation enthusiasts in 2001, Tradewind has grown a reputation for excellence, operating out of key strategic locations including Waterbury/Oxford, CT (OXC), Westchester, NY (HPN), Stuart, FL (SUA), and San Juan, PR (SJU). The company prides itself on providing superior aircraft, skilled crews, and professional service designed to meet the needs of both private and scheduled air travel customers throughout North America and the Caribbean. Tradewind Aviation emphasizes safety, operational reliability, and customer satisfaction as... Show More

Job Requirements

  • Bachelor's degree or equivalent aviation experience
  • valid commercial pilot or ATP license with appropriate type ratings
  • minimum of 5 years flight experience in Part 135 operations
  • strong understanding of FAA Part 135 regulations
  • previous leadership or supervisory experience in an aviation environment
  • excellent communication and interpersonal skills
  • ability to handle operational issues promptly and professionally
  • commitment to safety and regulatory compliance
  • flexibility to support on-call duties and occasional travel

Job 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

Job Duties

  • 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
  • support the Chief Pilot in maintaining compliance with FAA regulations, company manuals, and operational standards
  • assist in maintaining operational control and facilitate communication between flight crews, Dispatch, and leadership
  • conduct pilot evaluation, ground and flight training, base-level standardization, and recurrent/proficiency activities as assigned

Job Qualifications

Experience

Mid Level (3-7 years)

Job Location

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