Tradewind Aviation | Chief Pilot

About Tradewind Aviation

Tradewind Aviation is a premier Part 135 commuter and on-demand private charter operator. Founded in 2001, Tradewind is dedicated to providing the highest quality aircraft, crew, and service for both personal air travel and scheduled services across North America and the Caribbean.

Job Summary

Tradewind Aviation is actively seeking experienced and dedicated Regional Chief Pilots to oversee operations for its Northeast region, based at Westchester, NY (HPN). This pivotal role requires a proactive aviation leader committed to safety, operational excellence, and robust pilot support within a dynamic environment. The Regional Chief Pilot will work collaboratively with the Chief Pilot and company leadership to manage daily flight operations, supervise pilot activities, and ensure strict adherence to FAA regulations, company policies, and Tradewind’s established safety culture. This position is primarily office-based with minimal flying responsibilities.

Key Responsibilities

Pilot Leadership & Oversight

• Provide direct supervision, guidance, and support to assigned flight crewmembers.
• Address operational, performance, and safety concerns promptly and professionally.
• Ensure pilots comply with company procedures, regulatory requirements, and safety standards.
• Foster a positive, transparent, and accessible leadership presence for pilots.

Operational Support & Compliance

• Support the Chief Pilot in maintaining compliance with FAA regulations, company manuals, and operational standards.
• Facilitate communication between flight crews, Dispatch, and leadership, and assist in maintaining operational control.
• Monitor crew qualifications, scheduling requirements, and mission readiness for the assigned region.
• Ensure adherence to the General Operations Manual and all other company directives.

Training & Checking

• Conduct pilot evaluations, ground and flight training, base-level standardization, and recurrent/proficiency activities.
• Assist the Director of Operations and Director of Training in evaluating and improving training programs.
• Stay informed of aviation regulations, company policy updates, and industry best practices, disseminating relevant information to flight crews.

Administration & Base Management

• Act as the primary point of contact for region-specific pilot issues, operational needs, and personnel support.
• Contribute to performance evaluations, coaching, documentation, and follow-up actions.
• Participate in pilot recruitment, interviewing, and onboarding processes for the assigned region.
• Coordinate regional initiatives, pilot meetings, and local operational enhancements.

Cross-Functional Collaboration

• Collaborate with the Chief Pilot, SVP of Operations, Director of Operations, Director of Training, and Safety Department to align regional activities with company objectives.
• Support safety investigations, corrective action plans, and proactive safety programs.

Flying & Operational Duties

• Perform limited line flying as necessary for training, checking, and operational continuity.
• Maintain personal flight qualifications and currency according to company policies and FAA requirements.

Other Duties

• Undertake additional assignments as directed by the Chief Pilot.

Qualifications

• Possession of a Commercial or ATP certificate with relevant ratings for company operations.
• In-depth knowledge of FAA Part 135 regulations and operational mandates.
• Prior experience in pilot leadership, supervision, or pilot development is strongly preferred.
• Exceptional communication, interpersonal, and problem-solving abilities.
• Flexibility in work schedule, including availability for on-call operational needs and occasional travel.
• A proven dedication to safety, professionalism, and maintaining high operational standards.