Assistant Chief Pilot, Northeast Operations; HPN

Tradewind Aviation is seeking a full-time Assistant Chief Pilot to support its Northeast operations at HPN in West Harrison, New York. Working closely with the Chief Pilot and company leadership, you will drive daily flight operations, regional pilot activity, regulatory compliance, safety, and pilot development. This is primarily an in-office leadership role with limited flying responsibilities, including assignments for training, checking, and operational continuity.

• Serve as the regional point of contact for pilots, providing operational guidance and assistance; identify and elevate operational, performance, and safety concerns; and support compliance through regular communication and follow-up.
• Build positive relationships with flight crews, facilitate communication with leadership, and foster pilot engagement in a collaborative, professional team environment.
• Assist the Chief Pilot with FAA compliance, company manuals, operational standards, and operational control.
• Coordinate communication among crews, Dispatch, and leadership; monitor crew qualifications, scheduling requirements, and mission readiness; and ensure adherence to the General Operations Manual and other company guidance.
• Conduct assigned pilot evaluations, ground and flight training, base-level standardization, and recurrent/proficiency activities.
• Support the Director of Operations and Director of Training in evaluating and improving training programs; stay current on regulations, company policies, and industry best practices; and communicate relevant updates to crews.
• Act as the primary liaison for regional pilot issues, operational needs, and personnel support.
• Assist with performance evaluations, coaching, documentation, and follow-up; participate in recruiting, interviewing, and onboarding; and coordinate pilot meetings, initiatives, 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 actions, and proactive safety initiatives.
• Perform limited line flying as required for training, checking, and operational continuity; maintain personal qualifications and currency; and carry out additional assignments from the Chief Pilot.

• Commercial (CPL) or Airline Transport Pilot (ATP - unrestricted or restricted) certificate with appropriate ratings for company operations.
• Strong knowledge of FAA Part 135 regulations and operational requirements.
• Previous experience in supervision and/or pilot development strongly preferred.
• Excellent communication, interpersonal, and problem-solving skills, with a demonstrated commitment to safety, professionalism, and high operational standards.
• Flexibility to support on-call operational needs and occasional travel.
• Ability to maintain personal qualifications and currency per company policies and FAA requirements.

License requirement: CPL or ATP (unrestricted/restricted) with appropriate ratings

• Annual salary: $110,000-$180,000, commensurate with experience.
• Comprehensive health and voluntary insurance plans, retirement plan with company match, and paid time off.
• Travel benefits: standby travel on select Tradewind Aviation scheduled flights and discounted standby travel on numerous major and regional U.S. and international airlines.
• Career growth and advancement opportunities throughout the organization.