Chief Pilot

FlyUSA • Tampa, FL

1d • Onsite

About The Position

At FlyUSA, we're redefining the private aviation experience from start to finish. As leaders in the industry, we provide comprehensive solutions that meet the unique needs of our clientele. We're not just about flying; we're about delivering unparalleled service and creating memorable journeys. Position Overview: FlyUSA is seeking an experienced Chief Pilot to lead our Part 135 operations with the same precision and passion that define our flights. This leadership role combines operational oversight, active flying responsibilities, and strategic team development. The ideal candidate is a proven aviation leader who understands the technical and regulatory demands of Part 135 operations and knows how to build trust, inspire pilots, and foster a culture of unity, professionalism, and accountability. Location: Corporate Headquarters – Clearwater, Florida (with flexibility for a home base) Why FlyUSA? At FlyUSA, we are redefining what it means to lead in private aviation. We do not just operate aircraft. We deliver experiences defined by precision, excellence, and care. Every member of our team plays a vital role in creating the standard for safety, service, and professionalism that our clients have come to expect. As Chief Pilot, you will help shape that standard from the front line. You will lead a talented and growing pilot group, guide operational performance, and inspire a culture built on trust, accountability, and pride. This is more than a leadership position. It is an opportunity to influence how private aviation is experienced. FlyUSA offers a comprehensive benefits package designed to support both your career and your life. Our medical plans are affordable and flexible, with options that keep coverage accessible to all team members. We provide a 401(k) with company match, voluntary disability and life insurance, and a range of additional benefits that promote stability and peace of mind. If you are looking to lead a world-class operation, join a company that values its people as much as its performance, and be part of something exceptional, FlyUSA is where you belong. Apply today and help us continue to raise the bar for private aviation. Equal Opportunity Employer FlyUSA Inc. provides equal employment opportunities to all employees and applicants and prohibits discrimination and harassment of any type, ensuring that all employment decisions are based on qualifications, merit, and business needs.

Requirements

• Proven experience as a Chief Pilot or Director of Operations under Part 135.
• Minimum three years as Pilot in Command under Part 121 or 135 operations.
• Demonstrated success leading a pilot group of 25 or more.
• In-depth understanding of FAA and ICAO regulations.
• Valid Airline Transport Pilot certificate and current medical.
• Minimum 5,000 total flight hours.
• Strong leadership, communication, and decision-making skills.
• Ability to thrive in a fast-paced, client-focused environment.
• Extensive experience in corporate or charter aviation.

Nice To Haves

• Type ratings in HS-125, CE-500 or DA-2000.
• Bachelor’s degree in aviation or related field.
• Prior experience operating Hawker 800, Citation Ultra, and/or Falcon 2000 aircraft.

Responsibilities

• Provide leadership and vision for all flight operations, ensuring safety, compliance, and operational excellence.
• Maintain full adherence to Part 135 regulations and company policies.
• Lead, mentor, and motivate a growing team of pilots while promoting collaboration, consistency, and exceptional service standards.
• Perform flight duties on qualified aircraft and lead by example in the cockpit.
• Partner with Maintenance, Scheduling, and HR to ensure seamless coordination across departments.
• Oversee pilot training, qualifications, and recurrent programs in alignment with regulatory and company standards.
• Participate in pilot hiring, onboarding, and career development initiatives.
• Ensure operational readiness by maintaining aircraft documentation, checklists, and performance data.
• Develop and execute strategies to improve safety, efficiency, and team engagement across the fleet.

Benefits

• FlyUSA offers a comprehensive benefits package designed to support both your career and your life.
• Our medical plans are affordable and flexible, with options that keep coverage accessible to all team members.
• We provide a 401(k) with company match, voluntary disability and life insurance, and a range of additional benefits that promote stability and peace of mind.

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Number of Employees: 101-250 employees