Assistant Chief Pilot

Tradewind Aviation LLC • Oxford, CT

just now • $110,000 - $180,000 • Onsite

About The Position

Tradewind Aviation is seeking a dedicated and experienced Assistant Chief Pilot to support our 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. The Assistant Chief Pilot 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

• Commercial or ATP certificate with appropriate ratings for company operations.
• Strong knowledge of FAA Part 135 regulations and operational requirements.
• Previous experience in 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.

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 trip executed in the assigned region.
• Ensure adherence to the General Operations Manual and other company guidance.
• 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.
• 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.
• 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.
• 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.
• Carry out additional assignments as assigned by the Chief Pilot

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed