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Remote Caribbean Pilot Jobs (NOW HIRING)

TekSky

Chief Operating Officer

Tallahassee, FL · On-site +1

... Caribbean first, then across the U.S. and beyond. You will be asked what is proven and what is ... Strong Preference • Remote-market, island, or austere operating experience - particularly where ...

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All JobsCaribbean Pilot JobsRemote Caribbean Pilot Jobs

Remote Caribbean Pilot information

See salary details

$49.5K

$130.9K

$201K

How much do remote caribbean pilot jobs pay per year?

As of Jul 14, 2026, the average yearly pay for remote 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 are some unique challenges faced by remote Caribbean pilots, and how can they prepare for them?

Remote Caribbean pilots often encounter unique challenges such as unpredictable weather patterns, limited ground-based navigation aids, and operating from smaller, less-equipped airstrips. To succeed, pilots should stay updated with local meteorological resources, maintain strong communication with air traffic control, and be proficient in using onboard avionics for navigation. Building local knowledge of island terrain and airport procedures is also crucial, as is staying flexible to adapt to changing operational conditions.

What is the difference between Remote Caribbean Pilot vs Remote Caribbean Flight Instructor?

AspectRemote Caribbean PilotRemote Caribbean Flight Instructor
Required CertificationsCommercial Pilot License (CPL), Airline Transport Pilot (ATP) preferredCertified Flight Instructor (CFI), CPL often required
Work EnvironmentFlying aircraft, remote or offshore locations, sometimes virtual supportTeaching students remotely, virtual instruction, flight simulators
Employer & Industry UsageAirlines, charter companies, offshore operationsFlight schools, training organizations, virtual instruction platforms

The Remote Caribbean Pilot primarily involves flying aircraft in remote or offshore settings, requiring advanced pilot certifications. In contrast, the Remote Caribbean Flight Instructor focuses on teaching and training pilots remotely, often via virtual platforms, with certifications like CFI. Both roles are essential in the aviation industry but differ in responsibilities and work environment.

What are the key skills and qualifications needed to thrive as a Remote Caribbean Pilot, and why are they important?

To thrive as a Remote Caribbean Pilot, you need a commercial pilot's license, strong navigational skills, and thorough knowledge of Caribbean airspace regulations. Familiarity with weather tracking systems, aircraft avionics, and flight planning software is essential. Excellent communication, decision-making, and adaptability are important soft skills for managing diverse and dynamic flying conditions remotely. These skills help ensure safe, efficient operations and responsive handling of challenges unique to remote Caribbean aviation.

What are Remote Caribbean Pilots?

Remote Caribbean Pilots are licensed maritime professionals who guide ships safely into and out of Caribbean ports, often using remote technology to assist navigation and communication. These pilots possess specialized knowledge of local sea conditions, harbor layouts, and regulations unique to Caribbean waters. They work to ensure the safe and efficient movement of vessels, reducing the risk of accidents or delays. With advancements in technology, some pilotage services can now be provided remotely, enabling pilots to direct ships using real-time data and communication tools from a distance.
What cities are hiring for Remote Caribbean Pilot jobs? Cities with the most Remote Caribbean Pilot job openings:
What are the most commonly searched types of Caribbean Pilot jobs? The most popular types of Caribbean Pilot jobs are:
What states have the most Remote Caribbean Pilot jobs? States with the most job openings for Remote Caribbean Pilot jobs include:
Remote Caribbean Pilot jobs near you
Infographic showing various Remote Caribbean Pilot job openings in the United States as of July 2026, with employment types broken down into 2% As Needed, 87% Full Time, 10% Part Time, and 1% Contract. 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.
Chief Operating Officer

Chief Operating Officer

TekSky

Tallahassee, FL • On-site, Remote

Full-time

Posted 2 days ago

New

Job description

The Role
The COO is the operator-in-chief. This person owns execution across flight operations, maintenance, compliance, engineering, commercial delivery, and government-facing work. They are responsible for turning a compelling thesis into a live, scheduled, economically defensible cargo operation - in the Caribbean first, then across the U.S. and beyond.
You will be asked what is proven and what is still pending. What the real unit economics look like. What breaks in bad weather. What approvals are actually in hand. What the path into defense and government business really looks like. The right COO answers those questions from experience and judgment - not from a memo.
Non-Negotiable Experience
• Built and led complex aviation operations in a regulated, high-consequence environment - with personal accountability for safety, operating readiness, execution discipline, and economic performance in live flight operations. Scheduled Part 135 cargo experience is highly desirable.
• Direct FAA experience tied to bringing new or nonstandard operations to market: certification pathways, operating approvals, waiver and exemption strategy, and regulator-facing problem solving across multiple stakeholders.
• Ability to build constructive, credible working relationships with the FAA and international civil aviation authorities. Experience navigating the space where regulatory, political, and institutional considerations intersect - not just the formal technical process.
• Able to build, pressure-test, and defend a fully burdened aviation operating model - including maintenance, asset life, labor, insurance, compliance overhead, weather exposure, dispatch realities, and capital efficiency.
• Demonstrated ability to lead across functions: flight operations, maintenance, compliance, engineering, commercial execution, and government-facing work simultaneously.
Strong Preference
• Remote-market, island, or austere operating experience - particularly where local regulatory relationships, political dynamics, and operational execution must be managed in parallel.
• Civilian or military pilot experience, especially where it reflects real operational judgment in challenging environments. Flight instructor experience is also valuable.
• Military logistics or defense-mission exposure relevant to tactical resupply, field reliability, mission planning, or public-sector procurement. DoD acquisition fluency - including OTA or rapid-fielding pathways - is a real advantage.
• Experience converting customer interest into contracted demand: take-or-pay structures, government retainers, or repeatable institutional partnerships.
• Cold-chain or other high-reliability specialty logistics experience.
What We Are Not Looking For
• A large-airline executive who has never built in ambiguity.
• A last-mile drone specialist whose experience does not translate to heavier aircraft, longer routes, or serious regulatory and economic constraints.
• A technology executive who treats flight operations as someone else's problem.
• Anyone who approaches regulators as a box-checking exercise or autonomy as a science project.
What You Will Own
• Phase 1 commercial launch: scheduled Caribbean cargo operations from first flight to route-level EBITDA.
• Fully burdened unit economics: documented, verified, and defensible to institutional investors and the board.
• FAA and international regulatory strategy: approvals in hand, not pending assumptions.
• Fleet acquisition, readiness, and uptime across all operating aircraft.
• Commercial execution: take-or-pay contracts, carrier partnerships (FedEx, DHL, Amazon), and government retainers.
• Defense track entry: Army tactical resupply trials, SOFWERX demonstrations, and dual-use contract structure.
• Operational scaling from the Caribbean to U.S. and international markets.
Key Numbers You Will Be Accountable For
• 400 lbs payload | 200+ mile range | <$0.01/lb-mile operating cost
• Fleet uptime target: >80% through Phase 1
• Phase 1 gate: 6 months of on-time scheduled service on at least one Caribbean route
• At least one signed take-or-pay contract before Phase 2 capital is raised
• Regulatory approval in at least two Caribbean jurisdictions
• At least one DoD demonstration completed

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