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Day Shift Caribbean Pilot Jobs (NOW HIRING)

AIRMED INTERNATIONAL

Fixed Wing Pilot

San Antonio, TX · On-site

$111K - $122K/yr

Pilot shift assignments consist of either a day duty period or a night duty period and are scheduled the month prior by the Base Lead Pilot to provide pilots sufficient opportunity to prepare their ...

Global Medical Response

Fixed Wing Pilot

San Antonio, TX · On-site

$111K - $122K/yr

Pilot shift assignments consist of either a day duty period or a night duty period and are scheduled the month prior by the Base Lead Pilot to provide pilots sufficient opportunity to prepare their ...

Makers Air

Chief Pilot

Fort Lauderdale, FL

This hands-on leadership role is responsible for overseeing pilot performance, regulatory ... Caribbean, and Canada for periods of days to weeks as required for training, repairs or other ...

AIRMED INTERNATIONAL

Fixed Wing Pilot

San Antonio, TX · On-site

$111K - $122K/yr

Pilot shift assignments consist of either a day duty period or a night duty period and are scheduled the month prior by the Base Lead Pilot to provide pilots sufficient opportunity to prepare their ...

Global Medical Response

Fixed Wing Pilot

San Antonio, TX

$111K - $122K/yr

Pilot shift assignments consist of either a day duty period or a night duty period and are scheduled the month prior by the Base Lead Pilot to provide pilots sufficient opportunity to prepare their ...

Makers Air

Chief Pilot

Fort Lauderdale, FL

This hands-on leadership role is responsible for overseeing pilot performance, regulatory ... Caribbean, and Canada for periods of days to weeks as required for training, repairs or other ...

Makers Air

Chief Pilot

Fort Lauderdale, FL · On-site

This hands-on leadership role is responsible for overseeing pilot performance, regulatory ... Caribbean, and Canada for periods of days to weeks as required for training, repairs or other ...

Makers Air

Chief Pilot

Fort Lauderdale, FL · On-site

This hands-on leadership role is responsible for overseeing pilot performance, regulatory ... Caribbean, and Canada for periods of days to weeks as required for training, repairs or other ...

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All JobsDay Shift Caribbean Pilot Jobs

Day Shift Caribbean Pilot information

See salary details

$49.5K

$130.9K

$201K

How much do day shift caribbean pilot jobs pay per year?

As of Jul 31, 2026, the average yearly pay for day shift caribbean pilot in the United States is $130,916.00, according to ZipRecruiter salary data. Most workers in this role earn between $100,000.00 and $155,000.00 per year, depending on experience, location, and employer.

What is the difference between Day Shift Caribbean Pilot vs Day Shift Caribbean Captain?

AspectDay Shift Caribbean PilotDay Shift Caribbean Captain
CertificationsCommercial Pilot License, Caribbean-specific certificationsSame as Pilot, plus Captain-specific endorsements
Work EnvironmentAircraft operation, flight planning, navigationSupervising crew, overseeing flight safety, decision-making
Industry UsageAirlines, charter services in Caribbean regionAirlines, private charters, cruise line support

The main difference between a Day Shift Caribbean Pilot and a Day Shift Caribbean Captain is the level of responsibility. Pilots operate the aircraft and handle navigation, while Captains oversee the entire flight operation, supervise crew, and make critical safety decisions. Both roles require similar certifications, but the Captain holds a higher leadership position within the flight crew.

What cities are hiring for Day Shift Caribbean Pilot jobs? Cities with the most Day Shift Caribbean Pilot job openings:
What states have the most Day Shift Caribbean Pilot jobs? States with the most job openings for Day Shift Caribbean Pilot jobs include:
What job categories do people searching Day Shift Caribbean Pilot jobs look for? The top searched job categories for Day Shift Caribbean Pilot jobs are:
Day Shift Caribbean Pilot jobs near you
Infographic showing various Day Shift Caribbean Pilot job openings in the United States as of July 2026, with employment types broken down into 34% Locum Tenens, 2% As Needed, 51% Full Time, 8% Part Time, 1% Contract, and 4% Summer. Highlights an 94% Physical, 1% Hybrid, and 5% Remote job distribution, with an average salary of $130,916 per year, or $62.9 per hour.

Northeast Regional Chief Pilot

Tradewind Aviation

East White Plains, NY • On-site

$155K - $200K/yr

Full-time

Medical, Retirement, PTO

Posted 29 days ago

Job description

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 www.flytradewind.com
Requirements
About the Candidate / Role
Tradewind Aviation is seeking dedicated and experienced Regional 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 Tradewind's safety culture.
This is primarily an in-office role, with limited flying responsibilities.
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.

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 Range:
$155k-$200k a year

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