09 July 2024

Tradewind Aviation, LLC | Chief Pilot

Oxford, CT, United States

Pilot - Chief Pilot
Oxford, CT


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

About the Candidate / role Tradewind Aviation is seeking an experienced Chief Pilot for our Oxford, CT base location. This position requires flexibility with work schedule, some travel and includes operational on-call responsibilities. As the Chief Pilot, you will play a crucial leadership role, overseeing the pilot group and ensuring compliance with FAA regulations, company policies, and safety standards. This is primarily an office job with limited flying responsibilities.


* D irect supervision of all flight crewmember activities, including providing guidance and support to flight crews, addresses any operational issues or safety concerns, and ensures that all crewmembers adhere to established protocols and procedures throughout their duties.

* Manage a team of base Assistant Chief Pilots

* Collaborate with the SVP or Operations, Director of Operations, and Director of Training, to ensure compliance with FAA regulations, company standards, and manuals.

* Direct flight crews in operational activities and maintain operational control.

* Ensure flight crews are appropriately trained and qualified for assigned positions and missions.

* Maintain compliance with Federal Regulations and training program requirements for all aspects of flight crew training.

* Evaluate and enhance current training programs in collaboration with the Director of Operations and Director of Training.

* Stay updated on aviation regulations, advisories, and manuals, disseminating relevant information to flight crews.

* Ensure adherence to the General Operations Manual and Procedures Documents by flight crews.

* While delegation of tasks is permitted, ultimate responsibility for assigned functions remains with the Chief Pilot.

* Previous experience with managing/developing a large team of individual contributors.

Assume additional duties as assigned, including acting as Director of Operations if necessary.



* ATP or Type Rating preferred

* Meets the requirements of 14 CFR 119.71 or has a waiver from the FAA to serve in this position.

Physical Demands:

Prolonged periods of sitting at a desk and working at a computer

Physical requirements (lift 50lbs etc.)


* Competitive salary

* Medical, Dental, Vision, Life, STD, LTD, FSA/DCA and 401(k) plan.

* Paid vacation and sick days

* Paid Parental Leave

* Fun, dynamic team with opportunities for rapid advancement


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