SJU Assistant Chief Pilot

Position: SJU Base Assistant Chief Pilot

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.

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About the Role / Candidate

Tradewind Aviation is seeking dedicated and experienced Base 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.

Requirements Essential Functions

• Pilot leadership & oversight
• Provide direct supervision guidance and support to flight crew members 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.

Operational Support & Compliance

• 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 in the assigned region.
• Ensure adherence to the General Operations Manual and other company guidance.

Training & Checking

• 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.

Administration & Base Management

• 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.

Cross‑Functional Collaboration

• 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.

Flying & Operational Duties

• 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.

Other Duties

• Carry out additional assignments as assigned by the Chief Pilot.

Qualifications

• 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.

Required Experience

Chief

Key Skills

• Quality Assurance
• Transportation Management Systems
• Data Collection
• Military Experience
• Agriculture
• Federal Aviation Regulations
• Library Services
• Microsoft Power point
• LMS
• Teaching
• Exercise Planning
• Aviation Experience

Employment Type

Full Time

Experience

years

Vacancy

1

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