Assistant Caribbean Pilot Jobs (NOW HIRING)

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.

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 for trip executed 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.