Northeast Regional Chief Pilot

Job Type

Full-time

Description

About Tradewind

Tradewind Aviation is a leading Part 135 commuter and on-demand private charter operator with operational bases at the Waterbury/Oxford, CT (OXC), Westchester, NY (HPN), Stuart, FL (SUA) and San Juan,PR (SJU) airports. Founded by aviation enthusiasts in 2001 on the premise that all flights deserve the highest quality aircraft, crew, and service, Tradewind provides personal air travel-both private and scheduled service-throughout North America and the Caribbean.

For more details visit www.flytradewind.com

Requirements

About the Candidate / Role

Tradewind Aviation is seeking dedicated and experienced Regional Chief Pilots to support our Northeast (HPN), Southeast (SUA) and Caribbean (SJU) 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.

Base Chief Pilots 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.

Essential Functions

• Pilot leadership & oversight
• Provide direct supervision, guidance, and support to flight crewmembers assigned to the region.
• Address operational, performance, and safety concerns in a timely and professional manner.
• Ensure pilots adhere to established company procedures, regulatory requirements, and safety standards.
• Serve as an accessible leadership presence for pilots, promoting a positive and transparent culture.

• 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

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