PASS™ by PilotAssessments
Prepare Today, PASS Tomorrow
Chief Pilot, Boeing 757 — Global VIP Charter (Florida-based)
✈️ Chief Pilot — Boeing 757 (Global VIP Charter)
Lead a boutique, worldwide VIP charter operation as the Chief Pilot for Freedom II Bermuda Limited. This hybrid Florida-based role blends frontline Boeing 757 flying with day-to-day leadership of a small, high-performing crew operating under a Bermuda Part 121 AOC.
🧭 The Opportunity
As Chief Pilot, you will champion safety, standards, and crew excellence while flying global missions on the Boeing 757. Reporting to the Director of Operations, you will shape a positive, inclusive culture and ensure seamless international operations across diverse destinations.
🧰 What You’ll Do
- Provide day-to-day operational leadership and foster a safety-first, inclusive crew environment.
- Oversee flight crew standards, SOP adherence, line checks, and professional development.
- Support recruitment, selection, and onboarding of flight crew; manage rostering and scheduling.
- Coordinate recurrent training and currency requirements, including long-range and international operations.
- Ensure regulatory compliance, including BCAA validations and OTAR processes.
- Serve as key liaison with the Director of Operations, training providers, regulators, and operational partners.
- Plan and operate international missions safely, punctually, and cost-effectively.
- Collaborate closely with cabin crew, dispatch, ground handlers, maintenance control, and ATC.
- Fly the Boeing 757 on worldwide VIP charter routes as rostered.
- Continuously improve SOPs, safety reporting, and operational resilience.
🌟 What You’ll Bring
- Strong Boeing 757 experience with proven international operating background.
- Sound judgment and the ability to lead by example.
- Professional, approachable, and calm under pressure with excellent people skills and discretion.
- BCAA and/or OTAR experience is helpful but not required.
🧾 Key Details
- Reporting Line: Director of Operations
- Base: Florida, United States (hybrid office/field)
- Travel: Significant international travel; tour-based flying with extended home time
Ideal candidates are adaptable, globally mobile, and committed to the highest standards of safety and service.
📨 How to Stand Out
Showcase recent Boeing 757 time, concrete examples of crew leadership, and any familiarity with BCAA validations or Bermuda AOC operations.