Assistant Chief Pilot — Regional Ops & Training Lead

Tradewind Aviation, LLC; Town/Village of Harrison (NY); On-site; USD 110,000 - 180,000; Full time

Benefits offered by this job

Comprehensive health insurance

Voluntary insurance plans

Retirement plan with company match

Paid time off

Standby travel on Tradewind flights

Discounted standby travel on major and

regional airlines

Growth and advancement opportunities

Job summary

Tradewind Aviation is seeking an Assistant Chief Pilot to support Northeast operations from the HPN region, reporting to the Chief Pilot. The role focuses on safety, regulatory compliance, and pilot support with limited flying responsibilities.

You will work with leadership to ensure operational excellence, oversee pilot activities, and help maintain Tradewind’s safety culture while coordinating with Dispatch and Training teams.

Qualifications

• Excellent communication, interpersonal, and problem-solving skills.
• Ability to work flexibly, support on-call operational needs, and travel occasionally.
• Strong knowledge of FAA Part 135 regulations and operational requirements.
• Previous supervision or pilot development experience strongly preferred.

Responsibilities

• Serve as a point of contact for pilots within the region, providing guidance and assistance on operational matters.
• Help identify and elevate operational, performance, or safety concerns to appropriate leadership for review and resolution.
• Support compliance with company procedures, regulatory requirements, and safety standards through regular communication and follow-up.
• Foster positive working relationships with flight crews and promote effective communication between pilots and leadership.
• Assist with pilot engagement initiatives and help maintain a collaborative and professional team environment.
• 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 trips in the region.
• Ensure adherence to the General Operations Manual and other company guidance.
• Conduct pilot evaluation, ground and flight training, base-level standardization, and recurrent activities.
• Support the Director of Operations and Director of Training in evaluating and enhancing training programs.

Skills

Communication

Interpersonal

Problem-solving

Leadership

Flexibility

Education

Commercial or ATP certificate

Job description

Tradewind Aviation is seeking an Assistant Chief Pilot to support Northeast operations from the HPN region, reporting to the Chief Pilot. The role focuses on safety, regulatory compliance, and pilot support with limited flying responsibilities.

You will work with leadership to ensure operational excellence, oversee pilot activities, and help maintain Tradewind’s safety culture while coordinating with Dispatch and Training teams.