HUD SONiCJOBS

Tradewinds Airlines · United States · Posted Sep 6, 2026

Management

NTRCPL · FAAFull-time

Job description

Tradewind Aviation is seeking a dedicated and experienced Northeast Regional Chief Pilot to support Northeast (HPN) 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. Essential Functions: - 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. - 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. - 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. - 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. - Perform limited line flying as required, including missions supporting training, checking, and operational continuity. 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. Salary Range: $155,000–$200,000 per year.

Additional requirements

  • Strong knowledge of FAA Part 135 regulations and operational requirements

Compensation and Benefits

$155,000 – $200,000 per year (USD)

Medical insurance
  • Comprehensive health and voluntary insurance plans
  • Retirement plan with company match
  • Paid time off
  • Standby travel on select Tradewind Aviation scheduled flights
  • Discounted standby travel benefits on numerous major and regional US and international airlines
  • Opportunities for growth and advancement throughout the organization

Base Location

United States

Westchester County Airport (HPN / KHPN)