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 travelboth private and scheduled servicethroughout North America and the Caribbean.
For more details visit
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 Tradewinds 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 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.
Required Experience:
Chief
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 flight...
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 travelboth private and scheduled servicethroughout North America and the Caribbean.
For more details visit
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 Tradewinds 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 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.
Required Experience:
Chief
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