Chief Pilot, Boeing 757 - Global VIP Charter (Florida-based)

Pilot Assessments

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.

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Vacancy posted 2 days ago

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