About This Role
Tradewind Aviation is seeking a full-time Assistant Chief Pilot to support its Northeast operations at HPN, based in West Harrison, New York. Tradewind operates Part 135 commuter and on-demand private charter services throughout North America and the Caribbean. Working closely with the Chief Pilot and company leadership, the Assistant Chief Pilot supports 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 supporting training, checking, and operational continuity.
Duties & Responsibilities
- Serve as a regional point of contact for pilots, providing operational guidance and assistance, identifying and escalating operational, performance, and safety concerns, and supporting compliance through regular communication and follow-up. Build positive relationships with flight crews, facilitate communication with leadership, and support pilot engagement and 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 for trips in the region
- 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 or proficiency activities. Support the Director of Operations and Director of Training in evaluating and improving training programs, maintain current knowledge of 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.
What We Offer
Annual salary ranges from $110,000 to $180,000.Full-time team members receive comprehensive health and voluntary insurance plans, a retirement plan with company match, and paid time off.Travel benefits include standby travel on select Tradewind Aviation scheduled flights and discounted standby travel on numerous major and regional US and international airlines.Tradewind also offers career growth and advancement opportunities throughout the organization.
Requirements
- Applicants must hold a Commercial or ATP certificate with appropriate ratings for company operations and have strong knowledge of FAA Part 135 regulations and operational requirements.
- Previous experience in supervision or pilot development is strongly preferred.
- Candidates must demonstrate excellent communication, interpersonal, and problem-solving skills, together with a commitment to safety, professionalism, and high operational standards.
- The role requires flexibility, support for on-call operational needs, and occasional travel.
- The successful candidate must maintain personal qualifications and currency in accordance with company policies and FAA requirements.