Assistant Chief Pilot- Northeast

Tradewind • West Harrison, NY

25d • Onsite

About The Position

Tradewind Aviation is seeking a dedicated and experienced Assistant Chief Pilot to support its Northeast (HPN) operations. This primarily in-office leadership role has limited flying responsibilities and supports day-to-day flight operations, pilot activity, regulatory compliance, operational excellence, and pilot support. The Assistant Chief Pilot works closely with the Chief Pilot and company leadership to uphold FAA regulations, company policies, and Tradewind’s safety culture.

The role includes supporting and coordinating pilots in the region; assisting with operational control, compliance, crew qualifications, scheduling readiness, and communication among flight crews, Dispatch, and leadership; and conducting pilot evaluation, ground and flight training, standardization, and recurrent or proficiency activities as assigned. It also involves regional pilot administration and base management, recruiting and onboarding, safety initiatives and investigations, cross-functional collaboration, and limited line flying for training, checking, and operational continuity. The position requires maintaining personal qualifications and currency under company policies and FAA requirements, and may involve flexible support for on-call needs and occasional travel.

Requirements

• Commercial or ATP certificate with appropriate ratings for company operations.
• 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.

Nice To Haves

• Previous experience in supervision or pilot development is strongly preferred.

Responsibilities

• Serve as a point of contact for regional pilots and provide guidance on operational matters.
• Identify and elevate operational, performance, or safety concerns to appropriate leadership.
• Support compliance with company procedures, regulatory requirements, and safety standards through communication and follow-up.
• Foster effective communication and positive working relationships between flight crews and leadership; support pilot engagement and a collaborative team environment.
• Assist the Chief Pilot in maintaining compliance with FAA regulations, company manuals, and operational standards.
• Assist in maintaining operational control and facilitating communication among flight crews, Dispatch, and leadership.
• Monitor crew qualifications, scheduling requirements, and readiness for assigned missions 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 or proficiency activities as assigned.
• Support the Director of Operations and Director of Training in evaluating and enhancing training programs.
• Keep current on aviation regulations, company policy changes, and industry best practices, and share relevant updates with flight crews.
• Act 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 regional pilot recruiting, interviewing, and onboarding.
• Coordinate initiatives, pilot meetings, and local operational improvements.
• Collaborate with the Chief Pilot, SVP of Operations, Director of Operations, Director of Training, and Safety Department to align regional 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
• Career path with opportunities for growth and advancement throughout the organization

What This Job Offers

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