Chief Pilot

About the role

The Chief Pilot is responsible for overseeing flight operations, ensuring the safety and efficiency of all flights, managing flight crews, and maintaining compliance with aviation regulations and company policies. This role requires strong leadership, extensive aviation experience, excellent organizational skills, and the ability to align aviation operations with corporate goals and objectives. The position leads pilot and flight attendant performance, training, operational standardization, regulatory compliance, budget management, vendor coordination, and continuous improvement while promoting a culture of safety, professionalism, precision, and exceptional customer service across the flight department. Location: Rochester, New York. Full‑time, Aviation.

Responsibilities

• Safety and Regulatory Compliance: Promote and sustain a culture of safety; ensure all flight operations comply with FAA regulations, company policies, the Aviation Operations Manual, SOPs, and other authorities; lead Safety Management System initiatives, risk management, and incident reporting; participate in the Emergency Response Plan as a member of the Aviation Huddle Group.
• Flight Operations Leadership: Oversee and manage all flight operations to ensure safety, efficiency, service, and compliance; lead pilots, flight attendants, and Assistant Chief Pilots; collaborate with senior aviation leadership to align operations with corporate goals; supervise Assistant Chief Pilots; facilitate positive communication across the flight department.
• Training and Crew Development: Recruit, train, supervise, coach, and develop pilots and flight attendants; conduct performance evaluations; ensure pilots maintain required certifications, qualifications, training records, and readiness; manage and monitor flight crew training programs; strengthen leadership continuity and professional development.
• Operational Excellence and Precision: Develop, implement, and continuously improve SOPs for flight operations; stay current on industry trends and best practices; collaborate with Scheduling, Maintenance, and other stakeholders to support efficient aircraft utilization; drive consistency, discipline, attention to detail, and sound operational decision‑making.
• Customer Service and Passenger Experience: Ensure a high level of customer service for corporate clients, passengers, and internal stakeholders; address and resolve flight‑operation issues promptly; foster a safe, seamless, discreet, and professional passenger experience; build trust with internal customers, passengers, leadership, and cross‑functional partners.
• Administrative and Leadership Support: Manage the pilot training budget; optimize resource allocation for cost‑effective, reliable operations; monitor and control operational expenses; maintain vendor contracts; keep accurate operational, pilot, training, and compliance records; support audits, inspections, regulatory reviews, internal projects, and continuous‑improvement initiatives.
• Role Model and Professional Standards: Set the standard for professionalism, safety, precision, accountability, and service; lead by example and reinforce expectations for disciplined, compliant, and ethical operations; model integrity, preparation, respect, and sound judgment in all interactions.

Non‑Flying Responsibilities

• Dedicate approximately 10–20 hours per week of non‑flying time to strategic and operational leadership, safety, compliance, training, customer service, budget management, workforce planning, and continuous‑improvement initiatives.
• Lead department priorities, operational planning, and execution of flight‑operations objectives.
• Review and improve procedures, training materials, pilot readiness, and operational documentation.
• Advance safety initiatives, risk‑management practices, and proactive reporting culture.
• Coach pilots, flight attendants, and Assistant Chief Pilots while reinforcing expectations for professionalism, precision, service, and accountability.
• Contribute to projects, audits, process improvements, vendor management, budget oversight, and cross‑functional coordination with Scheduling and Maintenance.

Core Competencies

• Accelerate impact by challenging old ways and pursuing more efficient approaches.
• Balance workload, urgency, and business needs; set clear priorities and remove barriers.
• Model disciplined execution and accountability; drive department‑wide results through safe, reliable, compliant, and efficient flight operations.
• Prioritize work that strengthens operational performance, crew readiness, customer service, and alignment with business goals.
• Encourage idea‑sharing, respectful debate, and inclusive participation; ensure everyone feels heard.
• Promote collaboration, resolve conflict fairly, and recognize team contributions.
• Communicate expectations, priorities, and feedback clearly; create open dialogue and constructive feedback; share accurate information to keep alignment.
• Develop self and others through coaching, feedback, and continuous learning; support team growth plans and careers.
• Embrace change by adjusting plans quickly, guiding the team through change, encouraging smart risks, and modeling resilience.

Requirements

• Current FAA Airline Transport Pilot Certificate.
• Current FAA First Class Medical Certificate.
• Minimum 5,000 total flight hours, including 3,000 hours as Pilot‑in‑Command.
• Minimum 10 years of aviation‑operations experience, with at least 5 years in a leadership role.
• Type rating for at least one aircraft type operated by the company.
• Qualified under the Constellation Leasing LLC training program to act as Pilot‑in‑Command on one of the aircraft types.
• Ability to be away from home for extended periods to support domestic and international operations.
• Valid U.S. passport and driver’s license.
• Residence within one hour of Rochester International Airport (KROC).
• Successful completion of background investigation and pre‑employment drug screening.
• Demonstrated knowledge of the Company Operations Manual, training manuals, SOPs, and civil aviation regulations.
• Attendance at approved simulator training in the jet aircraft the pilot is type‑rated in within the previous 12 months.

Preferred Qualifications

• Bachelor’s degree, associate degree in Aviation Management, or NBAA Certified Aviation Manager certification.
• Gulfstream G280 and/or GVII type rating(s) preferred.
• International flight experience.
• Experience in IS‑BAO and/or Safety Management System (SMS) environments.
• Previous flight‑instruction experience or Certified Flight Instructor (CFI) certificate.

Pay

Salary range: $285,500.00 – $386,200.00 per year. Compensation is based on cost of labor and may vary according to factors such as location, education, qualifications, experience, skills, seniority, performance, and business needs.

Benefits

• Paid time off
• Medical, dental, and vision insurance
• 401(k) retirement plan
• Additional eligible employee benefits