Caribbean General Manager

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 a full-time Caribbean General Manager to oversee operations at our San Juan base and throughout the Caribbean Islands. Reporting to the SVP of Operations, this role is responsible for ensuring safe, efficient, and customer-focused operations. The ideal candidate will provide strong leadership to all personnel, manage existing locations, and drive the development of new locations across the region.

Safety is the top priority in this role. The Caribbean General Manager will lead by example, ensuring strict adherence to company policies, regulatory guidelines, and industry best practices to maintain a secure environment for passengers and staff across all areas of the SJU Airport and at remote locations. They will foster a culture where operational excellence, accountability and risk management come first.

Customer service is the key focus. The Caribbean General Manager will ensure their employees create a welcoming and professional atmosphere, ensuring that every client's interaction meets the highest service standards. They will empower the team to deliver seamless, efficient, and personalized experiences, enhancing passenger satisfaction at every touchpoint.

Finally, the Caribbean General Manager will provide strong leadership by offering clear direction, continuous communication, training, and ongoing support to the team. They will cultivate a positive and professional work culture that promotes teamwork, a sense of urgency, and encourages growth while holding still employees accountable. Flexibility is essential, as this position requires availability on weekends and holidays.

ESSENTIAL DUTIES

Safety & Compliance

• Ensure all operations comply with FAA, EASA, and ICAO regulations, company policies, TSA requirements, Domestic and International Customs regulations, and airport procedures.
• Oversee monthly safety and service audits to uphold operational excellence and regulatory compliance across all Caribbean locations.
• Maintain accurate and up-to-date station records, company documentation, and necessary permits as required by regulatory agencies.
• Proactively identify and mitigate safety risks, ensuring full compliance with OMNI reporting requirements and follow-up.
• Oversee SJU and outstation vendor negotiations, contracting, and service levels, conducting quarterly onsite audits to ensure adherence to agreements.
• Serve as the primary liaison with SJU, SBH, AXA, AXU, STT, VIJ and all other Caribbean airport administrations, safety, security, fixed base operators, and regulatory agencies, ensuring adherence to all local and federal guidelines.

Customer Service & Operations

• Oversee all customer service functions, ensuring seamless, efficient, and premium passenger experience. Stepping in when necessary.
• Maintain a high level of professionalism and effective communication with passengers, crew, and internal teams.
• Ensure daily operations run smoothly, efficiently, prioritizing on-time performance and service excellence.
• Track, measure, and continuous improvement on safety, service quality and operational efficiency initiatives.
• Ensure all Caribbean facilities, workspaces, equipment and aircraft are sufficient to meet demand, remain clean, safe, and well-maintained.

Leadership & Team Management

• Supervise and mentor the Station Manager and SJU base Admin fostering high morale, productivity, and accountability.
• Ensure appropriate base staffing and training is sufficient and completed annually.
• Conduct regular team meetings and station briefings, including ongoing training sessions to keep staff informed of updates, policies, and best practices.
• Handle HR-related functions, including performance evaluations, conflict resolution, and personnel record-keeping.
• Manage SJU base and Caribbean outstation accounting, billing reconciliation, and annual operations budget to maintain financial accountability.
• Drive the strategic development of new locations and opportunities across the Caribbean for Tradewind.
• Foster a collaborative, results-driven culture, encouraging continuous improvement and teamwork.

Other Responsibilities

• Carry out additional duties as assigned by the SVP of Operations.
• Other duties as assigned.

REQUIRED EDUCATION AND EXPERIENCE

• Fluent in English and Spanish (reading, writing, speaking, and comprehension).
• Able to efficiently use a computer for operational tasks with experience in using Microsoft Word, PowerPoint, and Excel.
• Demonstrates strong team leadership, staff development, conflict resolution, and negotiation abilities, combined with strategic planning and decision-making skills.
• Must be self-motivated and a team player with strong communication skills.
• Able to work under pressure and within time constraints to ensure timely flight dispatch.
• Possesses in-depth knowledge of airport operations and services, ensures safety and security compliance with FAA, TSA, and ICAO regulations, and brings a detail-oriented, proactive, and innovative approach to achieving operational excellence.
• Must always project a professional image.

Requirements

REQUIRED EDUCATION AND EXPERIENCE

• Fluent in English and Spanish (reading, writing, speaking, and comprehension).
• Able to efficiently use a computer for operational tasks with experience in using Microsoft Word, PowerPoint, and Excel.
• Demonstrates strong team leadership, staff development, conflict resolution, and negotiation abilities, combined with strategic planning and decision-making skills.
• Must be self-motivated and a team player with strong communication skills.
• Able to work under pressure and within time constraints to ensure timely flight dispatch.
• Possesses in-depth knowledge of airport operations and services, ensures safety and security compliance with FAA, TSA, and ICAO regulations, and brings a detail-oriented, proactive, and innovative approach to achieving operational excellence.
• Must always project a professional image.

PHYSICAL REQUIREMENTS

• Able to lift 60 lbs. at a time.
• Available to work weekends and holidays and require after-hours accessibility for personnel and management.
• Some travel required
• Prolonged periods of sitting at a desk and working on a computer.
• Exposed to outdoor elements such as rain, wind, and sun.

BENEFITS

• Competitive salary
• Medical, Dental, Vision, FSA/DCA and 401(k) plan.
• Paid vacation and sick days
• Paid Parental Leave
• Fun, dynamic team with opportunities for rapid advancement
• Travel benefits on various US and International airlines