Chief Pilot at Privateflite Aviation LLC – Sellersburg, Indiana

PrivateFlite Aviation is expanding — and we are building the leadership team to scale with it. As a vertically integrated aviation platform offering FBO services, FAA Part 145 Maintenance, Aircraft Management, and Part 135 Charter, we control the full client experience. Our charter operation is growing, our fleet is expanding, and our infrastructure investment is accelerating.

We are seeking a Chief Pilot who can lead from the front — operationally, culturally, and strategically. This is a key leadership role inside a scaling charter operation.

Mission: Provide the Ultimate Client Experience.

· Integrity

· We Before Me

· Commitment to Excellence

· Service-Centered Leadership

· Level 10 Attitude

· Always Be Winning

The Chief Pilot reports directly to the Director of Operations and is responsible for the performance, compliance, and professional development of all flight crew members. The Chief Pilot must meet the qualifications of 14 CFR §119.71(b) and be eligible to exercise Operational Control under §135.77.

· Lead all initial, recurrent, and upgrade training programs.

· Ensure compliance with FAA regulations, Ops Specs, and company SOPs.

· Oversee crew scheduling and duty/rest compliance.

· Exercise Operational Control under 14 CFR §135.77.

· Maintain pilot qualification records and regulatory documentation.

· Oversee AFM revisions and manufacturer updates.

· Recruit, mentor, and standardize flight crew members.

· Collaborate with Safety, Maintenance, Sales, and Flight Control departments.

· ATP Certificate with appropriate aircraft ratings.

· Qualified to serve as PIC in at least one company-operated aircraft.

· Meets 14 CFR §119.71 Chief Pilot requirements.

· Minimum 3 years PIC experience under Part 121 or 135 (per regulatory requirements).

· Strong knowledge of FAA regulations, Ops Specs, and Part 135 operations.

· Demonstrated leadership and decision-making capability.

· Previous supervisory or managerial leadership in flight operations.

· Prior Check Airman designation.

· Experience managing pilot training and standardization programs.

· Operational systems proficiency (scheduling, tracking, document management).

· Demonstrated commitment to safety culture and continuous improvement.

· Competitive executive-level salary

· 401(k)

· Health, Dental, Vision Insurance

· Life & Disability Insurance

· Paid Time Off