Remote Chief Pilot Jobs in Florida (NOW HIRING)

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