[Company] is a family-owned, professionally operated private aviation company. Everything private aviation lives here: aircraft management, charter, maintenance, sales, flight training, FBO services, and charter brokerage. We were the first to bring every sector of private aviation under one brand, and the best of what we are building is still ahead of us.

But here is what you really need to know: the energy at [Company] is different, and you will feel it from day one. We move with purpose and intensity, thinking strategically, acting decisively, and tackling challenges head-on. This is not a place for coasting. We expect excellence, ownership, and the drive to do things right even when it is harder. We push hard because we genuinely want to elevate the lives of our clients, our aircraft owners, and the people right next to us. Growth is not just happening around us. We are driving it together.

Bring your energy, your expertise, and your commitment to excellence and expect us to meet you with the same. You will have a voice, a real seat at the table, and the opportunity to grow in a company that is genuinely invested in your future. Expect it all.

Our Core Values

• Safety First. Above all else, we operate with the safety of our Team Members, clients, and guests as our top priority. No exceptions, no shortcuts.

• Do the Right Thing for the Long Term. We act ethically, think strategically, and make decisions built for the future. Our Team Members are empowered to choose the harder right over the easier wrong.

• Take Care of Each Other. When we take care of our people, our people take care of our clients and each other. We show up, listen first, and lift each other up.

• Relationships Matter. Our relationships with Team Members, clients, vendors, and the communities we serve are the foundation of our success. We keep our word and build trust one interaction at a time.

• Maintain Positivity. We celebrate wins, lift each other up, and bring optimism and solutions to every challenge. The energy we create together is a choice, and we choose well. 

Your Competitive Edge

• Base salary of $175,000.00 – $225,000.00 (annualized), depending on experience, paid bi-weekly.

• This position is classified as FLSA Exempt.

• Relocation assistance is available for candidates relocating to the greater Indianapolis, IN area.

Our commitment to "Take Care of Each Other" shows up in everything we offer: generous benefits, competitive wages, paid vacation and holidays, excellent training programs, and discounted flight training. You will join a tight-knit family where leadership is compassionate, transparent, and empowers you to achieve success, both for the business and your personal growth. 

Where You Make Your Mark

The Chief Pilot leads the pilot organization and owns the standards to which [Company] aircraft are operated, carrying accountability for the health, standardization, development, and future capacity of the pilot group. This is an administrative and leadership seat first: day-to-day pilot support, tactical problem solving, and routine oversight are carried out by the Assistant Chief Pilots, while the Chief Pilot interprets what they report for trends, exposure, and risk and makes the decisions that change the department’s future state. Flying continues on a limited support schedule to sustain qualification and firsthand visibility into standardization, and is never used to cover crew shortages.

Leadership, Management and Accountability

• Lead, manage, and hold accountable the Assistant Chief Pilots, ensuring each carries genuine tactical leadership of an assigned pilot group and assigned fleet segment rather than deferring that work upward.

• Own hiring, promotion, qualification, performance, and discipline outcomes for the pilot group, deciding the matters the Assistant Chief Pilots recommend and participate in.

• Ensure quarterly conversations are completed across the entire pilot group through the Assistant Chief Pilot structure, and act on the concerns and trends they surface.

• Develop the leadership bench by identifying, preparing, and advancing future Assistant Chief Pilots, check airmen, and pilot instructors.

• Explain the reasoning behind decisions made from Assistant Chief Pilot reporting so that strategic judgment is taught rather than guessed at, managing exceptions and trends rather than the pilot population case by case.

Pilot Organization Health and Standardization

• Own the health of the pilot organization, including standardization, communication, morale, utilization, rest, and quality of life.

• Set department-wide standardization policy and the standards to which [Company] aircraft are operated, holding the Assistant Chief Pilots accountable for enforcement and reporting.

• Maintain type currency and personal credibility through a limited support flying schedule, flying to sustain qualification, observe standardization firsthand, and stay connected to what the line actually experiences.

• Treat any sustained increase in Chief Pilot flying load as a staffing signal requiring resolution rather than a flexible expectation of the role.

• Participate in the Event Review Committee and act on safety trends affecting the pilot group.

Aircraft Operating Environment and Documentation

• Ensure every aircraft presents a standardized, correctly documented, professionally maintained operating environment for each crew that arrives at it.

• Own required onboard manuals, checklist currency and configuration, EFB content, and aircraft presentation standards.

• Ensure pilot-facing operational information is accurate, current, and reachable without escalation.

• Maintain compliance with company policy, the applicable Federal Aviation Regulations, and the manuals required under 14 CFR Part 135.

• Exercise operational control as authorized, including the authority to initiate, conduct, divert, or terminate a flight, and ensure crewmember flight, duty, and rest records are complete and compliant. 

Forward Staffing, Training and Quality of Life

• Maintain a thirty, sixty, ninety, and one-hundred-eighty-day view of staffing, training, PTO, qualification, fleet, and quality-of-life exposure.

• Anticipate and resolve staffing and qualification gaps before they constrain the operation.

• Coordinate with Training and the Operational Control Center so that training demand, PTO, and utilization are planned against one another rather than in isolation.

• Support recruiting, selection standards, and onboarding for incoming pilots, and partner with the Director of Operations on crew planning and organizational development.

• Review the structured weekly health reports submitted by the Assistant Chief Pilots, acting on exceptions and directing what requires a decision above their scope.

Pilot-Facing Systems and Standards Adoption

• Own the effectiveness, not merely the availability, of pilot-facing systems including EFB, ForeFlight, Avianis, MySky, Vocus, and Web Manuals.

• Monitor adoption and resolve the friction that prevents crews from using the tools as intended.

• Eliminate recurring pilot-facing friction rather than repeatedly absorbing it into the department.

• Maintain a communication and reporting rhythm with the Director of Operations and senior leadership, providing timely visibility into crew performance, operational risk, and workforce trends.

• Complete special projects and initiatives as needed, embracing opportunities to contribute to [Company]’s continued growth and success.

Who Thrives in This Seat

The Skills You Carry In

• ATP certificate, with 5,000 hours total flying time and 3,000 hours total pilot-in-command time.

• Three years as pilot-in-command in Part 121 or Part 135 operations, and prior Chief Pilot or Director of Operations experience in a Part 135 operation.

• Prior experience leading a pilot group of twenty-five or more, with demonstrated ability to hold crew members accountable while supporting their development and retention.

• Type rating and currency in an aircraft on the [Company] fleet, or the ability to obtain and maintain one, sufficient to serve as pilot-in-command and to conduct pilot evaluations and line checks.

• Full working knowledge of aviation standards and safe operating practices, 14 CFR Chapter 1, the company’s Operations Specifications, maintenance and airworthiness requirements, and the manual required by 14 CFR 135.21.

• Must currently reside in, or be willing to relocate to, the greater Indianapolis, IN area; must successfully pass a background check and pre-employment drug screening; deep alignment with [Company] core values is non-negotiable.

• This position is designated FAA Safety Sensitive and is subject to DOT and FAA random drug and alcohol testing throughout employment.

What This Role Asks of You

• This is an on-site administrative and leadership role based in Fishers, IN; leadership and administrative responsibilities are central to the position, and flight duty is limited and scheduled around them.

• Must maintain an active FAA medical certificate and all currency requirements necessary to serve as pilot-in-command and to conduct pilot flight evaluations and line checks.

• Physically able to perform flight duties, including boarding and operating company aircraft, extended periods at the controls, and sustained periods of concentrated attention.

• Occasional travel is required to support crew development, standardization observation, operational needs, and client engagement across the [Company] fleet and network.

• Valid state driver’s license required.