Jet Aviation Staffing - Chief Pilot, Challenger, Bedford, MA, Bed

Behind every seamless journey, is the perfect team. Since 1983, Jet Aviation Staffing has been supporting the industry’s most prominent aviation companies by attracting and placing top talent. With thousands of direct hire placements of crew members, maintenance professionals, support staff, management and executive positions, and many more disciplines, we continue to perfect the art of staffing. When you want to find the very best career opportunity, you can rely on a team of dedicated professionals. On behalf of our external customers, Jet Aviation Staffing upholds in-depth and extensive standards to ensure we are recommending the best talent. Dedicated to the details, our expertise ensures a perfect career opportunity match for each of our candidates and a seamless experience for our customer.

Position Summary

The Chief Pilot is responsible for the safe, efficient, and professional operation of the corporate flight department. This position provides leadership and day-to-day oversight of flight operations, flight crew, scheduling, training, standardization, and regulatory compliance for a private FAR Part 91 operation. The Chief Pilot works closely with the Aviation Director, aircraft owner or representative, maintenance personnel, cabin crew, and other internal and external partners to ensure each mission is executed safely, discreetly, efficiently, and to the highest standards of service.

The successful candidate will be a hands-on leader and active line pilot who demonstrates sound judgment, strong operational discipline, exceptional communication skills, and a service-oriented approach appropriate for a private corporate aviation environment.

Essential Duties and Responsibilities

Provide leadership and operational oversight for all flight activities conducted under FAR Part 91.

Serve as Pilot in Command as required and maintain currency and proficiency on assigned aircraft.

Promote a safety-first culture and ensure flight operations are conducted in accordance with applicable FAA regulations, company policies, aircraft limitations, and established operating procedures.

Develop, maintain, and continuously improve flight department policies, procedures, manuals, standard operating procedures (SOPs), and operating standards.

Exercise sound operational judgment regarding flight planning, weather, airport suitability, crew readiness, aircraft performance, international requirements, and overall mission risk.

Coordinate flight crew scheduling and staffing to ensure appropriate trip coverage, crew qualifications, rest, availability, and continuity of service.

Oversee pilot training, recurrent training, checking, currency, medical certificates, and qualification records.

Maintain accurate flight department records and ensure required operational documentation is current and properly maintained.

Participate in the recruitment, interviewing, selection, onboarding, development, and performance management of flight crew members.

Coach and mentor pilots, establish clear performance expectations, and foster a collaborative and professional crew environment.

Coordinate closely with maintenance personnel to support aircraft availability, discrepancy management, maintenance planning, and safe return-to-service decisions.

Partner with cabin crew, scheduling, aviation management, and external service providers to deliver seamless trip execution and an exceptional passenger experience.

Support domestic and international trip planning, including permits, customs, handling, security, ground transportation, and other mission-specific requirements as appropriate.

Maintain familiarity with international operating requirements and ensure crews are properly prepared for worldwide operations.

Participate in Safety Management System (SMS) activities, risk assessments, safety reporting, emergency response planning, and investigation of operational irregularities or incidents.

Identify operational risks and recommend practical solutions that support safety, reliability, service, and cost effectiveness.

Assist with annual operating plans, staffing requirements, training budgets, and other flight department planning as requested.

Develop and maintain productive relationships with the FAA, training providers, FBOs, vendors, OEM representatives, and other aviation partners as appropriate.

Protect the confidentiality and privacy of the aircraft owner, passengers, family members, guests, business activities, travel schedules, and flight department information.

Demonstrate flexibility to support changing schedules, short-notice travel, weekends, holidays, extended trips, and international missions as required by the operation.

Perform other aviation-related duties as assigned by the Aviation Director, aircraft owner, or designated representative.

Leadership and Service Expectations

Lead by example with professionalism, integrity, discretion, accountability, and sound decision-making.

Maintain a calm, solutions-oriented approach in dynamic and time-sensitive operating environments.

Build a strong team culture centered on safety, communication, mutual respect, standardization, and service.

Communicate effectively with principals, executive staff, family office personnel, crew members, and aviation partners.

Anticipate operational and passenger needs while maintaining appropriate boundaries between safety requirements and service expectations.

Represent the flight department professionally at all times.

Minimum Qualifications

FAA Airline Transport Pilot (ATP) certificate with appropriate airplane category and class ratings.

Current FAA First-Class Medical Certificate.

Appropriate type rating for the assigned aircraft, or ability to obtain the required type rating prior to assuming flight duties.

Minimum 5,000 hours total flight time preferred, with substantial turbine and multi-engine experience.

Demonstrated experience as Pilot in Command in corporate or business aviation; large-cabin or comparable aircraft experience preferred where applicable.

Strong working knowledge of FAR Part 91 operations, FAA regulations, flight planning, aircraft performance, international operations, and aviation safety practices.

Prior Chief Pilot, Lead Captain, Standards Captain, Director of Aviation, or comparable leadership experience strongly preferred.

Demonstrated experience managing or mentoring professional flight crews.

Excellent written and verbal communication skills.

Strong organizational, analytical, problem-solving, and decision-making skills.

Ability to work independently, manage competing priorities, and respond effectively to schedule changes.

Ability to travel domestically and internationally and work a flexible schedule based on operational requirements.

Valid passport and ability to meet all applicable travel and entry requirements.

Preferred Qualifications

Bachelor’s degree or equivalent combination of education and aviation experience.

Current or recent experience on the assigned aircraft type.

Extensive international and oceanic operating experience.

Experience with a corporate aviation Safety Management System (SMS), emergency response planning, and operational risk management.

Experience helping establish, transition, or improve a self-managed corporate flight department.

Knowledge of aviation budgeting, vendor management, training programs, and flight department administration.

NBAA Certified Aviation Manager (CAM) or other relevant professional certification is a plus.

Physical Demands and Work Environment

The physical demands described below are representative of those required to successfully perform the essential functions of this position. Reasonable accommodations may be made to enable qualified individuals with disabilities to perform essential job functions.

Ability to sit, stand, walk, reach, bend, climb aircraft stairs, and work in and around aircraft and airport environments.

Ability to lift and move baggage, supplies, or equipment consistent with normal flight department operations.

Ability to work in varying weather conditions, noise levels, time zones, and operational environments.

Must meet all medical, physical, and regulatory requirements necessary to perform ass

Jet Aviation provides equal employment and affirmative action opportunities to applicants and employees without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, protected veteran status, or disability.