Pilot - Caribbean Assistant Chief

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

About the Candidate / Role
Tradewind Aviation is seeking dedicated and experienced Assistant Chief Pilot to support our Northeast (HPN) 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. The Assistant Chief Pilot 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 Support & Coordination
Serve as a point of contact for pilots within the region, providing guidance and assistance on operational matters.
Help identify and elevate operational, performance, or safety concerns to appropriate leadership for review and resolution.
Support compliance with company procedures, regulatory requirements, and safety standards through regular communication and follow-up.
Foster positive working relationships with flight crews and promote effective communication between pilots and leadership.
Assist with pilot engagement initiatives and help maintain a collaborative and professional team environment.

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

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

Tradewind Aviation offers a competitive pay and benefits program for full-time team members:
Comprehensive health and voluntary insurance plans
Retirement plan with company match
Paid time off
Standby travel on select Tradewind Aviation scheduled flights
Discounted standby travel benefits on numerous major and regional US and international airlines
A rewarding career path with opportunities for growth and advancement throughout the organization

Salary Description
$110,000 - $180,000 per year