Chief Pilot

Career Area: Business Services Job Description: Your Work Shapes the World at Caterpillar Inc. When you join Caterpillar, you're joining a global team who cares not just about the work we do – but also about each other. We are the makers, problem solvers, and future world builders who are creating stronger, more sustainable communities. We don't just talk about progress and innovation here – we make it happen, with our customers, where we work and live. Together, we are building a better world, so we can all enjoy living in it. Caterpillar has an exciting opportunity for a Chief Pilot within Caterpillar Aviation Services. This role provides leadership and operational oversight for Caterpillar's corporate flight operations while also serving as a qualified pilot supporting company aircraft. The Chief Pilot is responsible for maintaining the highest standards of flight safety, operational readiness, regulatory compliance, pilot performance, and professional conduct. This individual will lead a team of professional pilots and cabin safety professionals supporting executive travel and partner closely with aviation leadership, maintenance, scheduling, and flight operations teams to ensure safe, efficient, and reliable operations. This highly visible leadership position supports Caterpillar's executive leadership team and requires strong judgment, technical aviation expertise, communication skills, and the ability to lead in a dynamic corporate aviation environment. What You Will Do Flight Operations Leadership Lead and oversee day-to-day pilot operations within Caterpillar Aviation Services. Provide operational leadership for Caterpillar's corporate flight department, ensuring adherence to safety standards, regulatory compliance, operational readiness, and service excellence. Provide leadership, coaching, and development to a team of approximately 10 pilots and 3 cabin safety professionals. Maintain pilot standards, operational readiness, regulatory compliance, flight section budget, and flight department procedures. Ensure effective pilot scheduling, reserve coverage, and crew availability to meet corporate travel requirements. Promote a culture of safety, professionalism, accountability, and operational excellence. Flight Operations & Safety Serve as a qualified pilot supporting executive transportation requirements worldwide. Support executive transportation activities for Caterpillar's senior leadership team, including executive officers, Group Presidents, Senior Vice Presidents, and other key stakeholders. Ensure flight planning, weather criteria, aircraft performance, and weight and balance requirements have been met prior to flight operations. Conduct or ensure completion of aircraft pre-flight inspections and passenger briefings in accordance with FAA regulations. Maintain compliance with FAA regulations, company policies, customs requirements, immigration requirements, and international operating requirements. Serve as the department leader for pilot safety standards and operational discipline. Support Safety Management System (SMS) initiatives and continuous improvement activities. Team Leadership & Development Provide coaching, mentorship, and professional development for flight crews. Partner with aviation training leadership to ensure pilot qualifications, certifications, and currency requirements are maintained. Support pilot recruiting, selection, development, and succession planning activities. Evaluate operational effectiveness and identify opportunities to improve procedures, safety, and efficiency. Business Partnership & Operational Coordination Collaborate with maintenance, scheduling, and aviation support personnel to maximize aircraft availability and operational readiness. Support executive transportation requirements while balancing safety, regulatory requirements, and operational efficiency. Serve as a trusted advisor on aviation operations, pilot standards, and flight department performance. What You Have FAA Airline Transport Pilot (ATP) Certificate. First-Class Medical Certificate issued by an FAA-certified physician. Minimum 10 years of relevant aviation experience including international flight operations. Significant fixed-wing flight experience, typically demonstrated by 3000+ flight hours . Instrument flight experience, including experience operating in complex aviation environments. Experience operating within a FAR Part 91 corporate aviation environment strongly preferred. Experience in one or more of the following: Corporate Aviation Operations FAR Part 135 Operations FAR Part 121 Aviation Operations Military Aviation Operations Demonstrated leadership experience supervising or leading pilots, cabin safety professionals (FA’s), aviation teams, or flight operations. Strong knowledge of FAA regulations, corporate aviation operations, and aviation safety standards. Exceptional leadership, organizational, decision-making, and communication skills. Clean safety and regulatory record with no accidents or violations. What Will Put You Ahead Gulfstream GVII and/or GVIII Type Ratings. Experience operating Gulfstream G500 and G700 aircraft. Experience in comparable large-cabin corporate aircraft. Chief Pilot, Assistant Chief Pilot, Chief of Training, Lead Captain, or Flight Operations leadership experience. Military aviation leadership experience. Experience supporting executive and corporate flight department operations. Experience managing pilot scheduling, crew readiness, training programs, and operational standards. Strong background in aviation safety programs and Safety Management Systems (SMS). Education Bachelor's degree and/or equivalent experience preferred. Why Join Us Opportunity to lead a highly respected corporate aviation operation supporting Caterpillar's global leadership team. Direct influence over flight operations, pilot development, safety standards, and operational excellence. Join a modern Gulfstream fleet supporting worldwide business operations. Leadership succession opportunity within Caterpillar Aviation Services. Frequent interaction with executive leadership and exposure to strategic business priorities. Additional Information Location: Fort Worth, Texas Relocation Assistance: Available for those who qualify Aviation Resume: Aviation-specific resume requested in addition to a traditional resume Executive Exposure: Frequent interaction supporting executives, including C-Suite leadership, Group Presidents, and Senior Vice Presidents Fleet: Modern Gulfstream fleet supporting global business operations Summary Pay Range: $177,720.00 - $266,590.00 Compensation and benefits offered may vary depending on multiple individualized factors, job level, market location, job-related knowledge, skills, individual performance and experience. Please note that salary is only one component of total compensation at Caterpillar. Benefits: Subject to plan eligibility, terms, and guidelines. This is a summary list of benefits. Medical, dental, and vision benefits* Paid time off plan (Vacation, Holidays, Volunteer, etc.)* 401(k) savings plans* Health Savings Account (HSA)* Flexible Spending Accounts (FSAs)* Health Lifestyle Programs* Employee Assistance Program* Voluntary Benefits and Employee Discounts* Career Development* Incentive bonus* Disability benefits Life Insurance Parental leave Adoption benefits Tuition Reimbursement * These benefits also apply to part-time employees Posting Dates: October 5, 2026 - October 19, 2026 Any offer of employment is conditioned upon the successful completion of a drug screen. Caterpillar is an Equal Opportunity Employer, Including Veterans and Individuals with Disabilities. Qualified applicants of any age are encouraged to apply. Not ready to apply? Join our Talent Community .