Freedom II is hiring a Chief Pilot – Boeing 757. This is a hybrid position with a Florida base to support our Bermuda Part 121 AOC.

This is a hands-on leadership role in a small, highly professional flight department operating long-range VIP charters worldwide. The flying may include extended periods on the road, followed by extended periods at home, so flexibility and a good understanding of this lifestyle are important.

The Chief Pilot reports to the Director of Operations and is responsible for the efficient management of Freedom II flight crews in accordance with OTAR requirements, company standards, and SOPs. The role includes flight crew oversight, standards, recruitment support, onboarding, BCAA validation paperwork, crew development, training coordination, rostering support, and day-to-day operational leadership.

We are looking for someone with strong Boeing 757 experience, sound judgment, international operating experience, and the ability to lead by example.

Because this is a small-company VIP charter environment, the right personality is just as important as the right qualifications. The successful candidate should be professional, approachable, calm under pressure, and able to communicate well with crews, clients, vendors, and regulators. Good people skills, discretion, and the ability to build trust within the team are essential.

BCAA/OTAR experience is helpful, but not required.

Please reach out directly to jobs@flyfreedom2.com if you are interested.

Freedom II Bermuda Limited

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