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Caribbean Aviation Jobs (NOW HIRING)

Tradewind Aviation

PR · On-site

For more details visit www.flytradewind.com ABOUT THE CANDIDATE / ROLE Tradewind Aviation is looking for a full-time San Juan Customer Service Supervisor to be based at our Caribbean base in San Juan ...

Tradewind Aviation LLC

PR · On-site

For more details visit www.flytradewind.com ABOUT THE CANDIDATE / ROLE Tradewind Aviation is looking for a full-time San Juan Customer Service Supervisor to be based at our Caribbean base in San Juan ...

Tradewind Aviation

Dispatcher

Oxford, CT · On-site

... Caribbean. For more details visit www.flytradewind.com ABOUT THE CANDIDATE / ROLE Tradewind Aviation is looking for a full-time Dispatcher to be based in Oxford, CT. Dispatchers ensure the safe and ...

Hertz

Private Aviation Specialist

Revere, MA · On-site

$22/hr

The Private Aviation Specialist will be responsible for assisting our private aviation business ... Caribbean, Latin America, Africa, the Middle East, Asia, Australia and New Zealand. The Hertz ...

Hertz

Private Aviation Specialist

Revere, MA · On-site

$22/hr

The Private Aviation Specialist will be responsible for assisting our private aviation business ... Caribbean, Latin America, Africa, the Middle East, Asia, Australia and New Zealand. The Hertz ...

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How much do caribbean aviation jobs pay per hour?

As of Jun 16, 2026, the average hourly pay for caribbean aviation in the United States is $21.54, according to ZipRecruiter salary data. Most workers in this role earn between $15.87 and $23.56 per hour, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive in the Caribbean Aviation position, and why are they important?

To thrive in Caribbean Aviation, professionals need a solid grounding in aviation operations, airline regulations, and safety standards, typically supported by an aviation degree or specialized certification such as an ATPL, AME, or FAA license. Familiarity with aviation management software, aircraft maintenance systems, and international flight planning tools is often required. Excellent communication, problem-solving skills, and adaptability to diverse multicultural environments set candidates apart in this sector. These abilities ensure safe, efficient, and customer-focused aviation operations across the unique geographic and regulatory landscape of the Caribbean.

What is a Caribbean Aviation job?

A Caribbean Aviation job involves working in the aviation industry within the Caribbean region, including roles in airlines, airports, air traffic control, and aircraft maintenance. These jobs can range from pilots and flight attendants to ground operations and aviation management. Due to the region's heavy reliance on air travel for tourism and trade, aviation professionals play a crucial role in ensuring safe and efficient transportation. Opportunities vary by country and employer, with some requiring specialized training or certifications.

What are some common challenges faced by professionals working in Caribbean Aviation?

Professionals in Caribbean Aviation often encounter unique logistical challenges due to the region’s geography, including operating flights between multiple islands and adapting to rapidly changing weather conditions. Navigating diverse regulatory requirements and maintaining strong safety standards across different jurisdictions is also essential. Teamwork and clear coordination are necessary, as aviation roles here frequently involve collaborating with local authorities, international airlines, and multicultural teams. Adapting quickly and staying informed about regional aviation updates will help you succeed and advance in this dynamic field.

More about Caribbean Aviation jobs
What are the most commonly searched types of Caribbean Aviation jobs? The most popular types of Caribbean Aviation jobs are:
What states have the most Caribbean Aviation jobs? States with the most job openings for Caribbean Aviation jobs include:
What job categories do people searching Caribbean Aviation jobs look for? The top searched job categories for Caribbean Aviation jobs are:
Caribbean Aviation jobs near you
Infographic showing various Caribbean Aviation job openings in the United States as of June 2026, with employment types broken down into 86% Full Time, and 14% Part Time. Highlights an 95% Physical, 1% Hybrid, and 4% Remote job distribution, with an average salary of $44,812 per year, or $21.5 per hour.
Customer Service Supervisor, San Juan

Customer Service Supervisor, San Juan

Tradewind Aviation

PR • On-site

Full-time

Medical, Retirement, PTO

Posted 13 days ago

Job description

Job Type
Full-time
Description
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 looking for a full-time San Juan Customer Service Supervisor to be based at our Caribbean base in San Juan, PR. This includes providing strong, positive leadership, guidance, and continuous training to the team in line with our company goals. They will promote and maintain a healthy work culture that produces excellent employee morale, and attracts the highest level of talent, while encouraging continuous growth. The Supervisor will consistently strive for top-tier customer service at every client interaction. Specifically, the San Juan Station Supervisor is responsible to:
RESPONSIBILITIES
  • Assist the San Juan Station Manager in overseeing and managing the Tradewind San Juan Station employees and services.
  • Ensure the day-to-day operation runs effectively in accordance with the established policies and procedures of the company and respective regulatory agencies
  • Be an expert in customer service
  • Efficiently coordinate and monitor all aspects of the operation
  • Ensure important information is being communicated appropriately between shifts
  • Liaison between company departments, vendors, and regulatory agencies
  • Develop and provide training and coaching to station personnel and vendors
  • Approve time off requests while maintaining appropriate staffing levels
  • Assist with recruitment and termination of employees
  • Responsible for always tracking and improving the quality of services provided by the San Juan Station
  • Measure and analyze employee performance and ensure all company procedures, protocols, and standards are followed by the employees
  • Be strategic in thought processes and decision-making
  • Develop and maintain documentation regarding employee conduct, client issues, feedback, and disciplinary actions
  • Take lead on service disruptions and direct appropriate follow-up
  • Observe safe ground handling procedures and maintenance of ground service equipment, including the performance of equipment checks
  • Ensure compliance of all safety procedures and airline policies
  • Ensure GOM procedures are always followed
  • Other duties as assigned by San Juan Station Manager or Caribbean General Manager

Requirements
QUALIFICATIONS
  • BS degree in a field related to business and/or management
  • 2 + years' work experience in a supervisory and leadership capacity, with general job knowledge
  • Able to proficiently read, write, speak, and understand English and Spanish
  • Able to work rotating shifts, schedules and able to work during nights, weekends and holidays
  • Able to successfully complete a background investigation, including FBI fingerprints and criminal history
  • Must be authorized to work in the U.S. or its territories without the need for future sponsorship
  • Must have a valid In-State Driver's License
  • Must be able to work under pressure and time constraints necessary to dispatch flights on time.
  • Must project a professional image
  • Proficient with Microsoft Word, Power Point and Excel
  • Self-motivated and a team player

PHYSICAL REQUIREMENTS
  • Ability to lift / push or pull, greater than or equal to 65 lbs.
  • Exposure to outdoor elements including heat, cold, rain, wind, and sun during ramp and operational duties.
  • Ability to communicate effectively on the phone and in meetings (in person or virtual)
  • Ability to use to operate a computer keyboard, mouse, and standard office equipment
  • Potential exposure to environmental factors such as: Aircraft fumes and exhaust

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

Part-time and Seasonal team members are eligible for specific benefits based on location and hours worked.

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