Chief Pilot – Corporate Aviation (Gulfstream Fleet)

🧭 What you’ll lead and do

• Provide day-to-day operational leadership for the pilot group; set professional standards and ensure operational discipline across the flight department.
• Serve as a qualified pilot for worldwide executive transportation supporting Executive Officers, Group Presidents, Senior Vice Presidents, and other key stakeholders.
• Own safety, regulatory compliance, and operational readiness; guide adherence to FAA, company, customs, immigration, and international operating requirements.
• Ensure robust flight planning, including weather, aircraft performance, weight-and-balance, and pre-flight inspections; confirm passenger briefings in accordance with regulations.
• Lead pilot scheduling strategy, reserve coverage, and crew availability to meet corporate travel demands while maintaining crew currency and duty-time protections.
• Coach, mentor, and develop flight crews; partner with training leadership to manage qualifications, certifications, currency, and recurrent programs.
• Drive Safety Management System (SMS) initiatives, continuous improvement, and proactive risk management.
• Collaborate with maintenance, scheduling, and aviation support teams to maximize aircraft availability and dispatch reliability.
• Manage the flight-section budget and contribute to flight-department procedures, standards, and performance metrics.
• Support pilot recruiting, selection, development, and succession planning; advise aviation leadership on operational standards and improvements.

🧰 What you bring

• License: ATP Certificate (Unrestricted or Restricted) and FAA First-Class Medical.
• Total Flight Time: 3,000+ hours, with substantial fixed-wing and instrument experience in complex operational environments.
• Experience: 10+ years of relevant aviation experience, including international flight operations.
• Leadership: Demonstrated experience supervising or leading pilots, cabin safety professionals, aviation teams, or flight operations.
• Knowledge: Strong command of FARs, corporate aviation operations, and aviation safety standards.
• Record: Clean safety and regulatory history with no accidents or violations.
• Background: Experience in one or more of corporate aviation, FAR Part 135, FAR Part 121, or military operations; FAR Part 91 corporate aviation strongly preferred.

🌟 Preferred qualifications

• Gulfstream GVII/GVIII type ratings; time on G500 and/or G700 or comparable large-cabin corporate aircraft.
• Chief Pilot or flight-operations leadership experience; military aviation leadership and/or executive flight-department experience.
• Hands-on experience managing scheduling, crew readiness, training programs, operational standards, safety programs, and SMS.
• Bachelor’s degree and/or equivalent experience.

💼 What success looks like

• Flawless safety performance and regulatory compliance across domestic and international missions.
• High crew engagement, professional standards, and a proactive safety culture.
• Reliable executive travel supported by smart scheduling, strong readiness, and excellent service quality.
• Continuous improvement of procedures, training, efficiency, and departmental performance.

🎁 Benefits and growth

Join a respected corporate aviation team supporting Caterpillar’s global leadership, with direct interaction with C‑Suite leaders and a clear leadership succession pathway. Relocation assistance available for qualified candidates. Subject to plan eligibility, benefits include:

• Medical, dental, and vision coverage; Health Savings Account and Flexible Spending Accounts.
• Paid vacation, holidays, and volunteer time.
• 401(k) savings plans.
• Health and lifestyle programs; Employee Assistance Program.
• Voluntary benefits, employee discounts, and career development.
• Incentive bonus opportunities.
• Disability benefits and life insurance.
• Parental and adoption benefits.
• Tuition reimbursement.

📨 Ready to lead?

If you’re a safety-first leader who thrives in complex international operations and enjoys mentoring high-performing crews, we’d love to hear from you. Bring your Gulfstream expertise and elevate corporate aviation at Caterpillar.