Regional Chief Pilot – Northeast Base 

Location: Westchester County Airport (KHPN) – White Plains, NY (Mandatory On-Site) 

Quick Facts: Schedule, Compensation & Benefits

• Position Type: Full-Time, Permanent W2 Leadership Position

• Compensation: $160,000 – $180,000 per year (Commensurate with leadership depth).

• Schedule: Monday – Friday base schedule.

• The Flight/Office Mix: Designed perfectly for a pilot transitioning into long-term aviation management. This is 95% in-office leadership and 5% line flying/training. You will take to the skies roughly once every two weeks, flying local Northeast routes (e.g., Teterboro, NJ, New York regional corridors).

• Fleet Type & Training: Operations are built around the Pilatus PC-12. If you do not hold a PC-12 type rating, our client will fully sponsor and assist you in obtaining this certification upon onboarding.

• Relocation Assistance: Available and negotiated on a case-by-case basis for the right top-tier leader. 

About Our Client

Our Client is a premier, award-winning Part 135 commuter and on-demand private charter operator providing exceptional air travel across North America and the Caribbean. Known for maintaining the highest standards of safety, aircraft quality, and crew culture, they have established themselves as an industry leader where pilots can truly build lasting careers.

This specific role is the ultimate next step for a charismatic, people-first pilot looking to transition into a highly visible, stable management position. As the Northeast Regional Chief Pilot, you will report directly to the overall Chief Pilot and serve as the operational backbone for the HPN base. You aren't just sitting in an office managing numbers—you will be the direct mentor, guide, and champion for a growing team of 95 pilots managing an impressive fleet of 38 aircraft.

The Role: Mentorship, Leadership & Operations

This position is heavily focused on developing people. A significant portion of your pilot crew consists of sharp, ambitious young aviators (primarily ages 22–26). Your mission is to mold them into elite professional pilots, teach them what it means to be phenomenal employees, and provide an accessible, transparent, and motivating leadership presence every single day.

Key Responsibilities:

• Pilot Mentorship & Leadership: Provide direct supervision, guidance, and daily support to 95 regional flight crewmembers. Address performance and operational issues with a constructive, coaching mindset.

• Operational Oversight: Work hand-in-hand with the Chief Pilot and company executives to support day-to-day flight operations, facilitate clear communication between crews and dispatch, and ensure tight operational control.

• Training & Checking: Conduct pilot evaluations, base-level standardization, ground/flight training, and recurrent proficiency checks as needed.

• Compliance & Administration: Maintain absolute regulatory compliance with FAA Part 135 requirements, company General Operations Manuals (GOM), and safety cultures. Assist with recruiting, interviewing, and onboarding new talent to the base.

Qualifications & Requirements

We are hunting for a magnetic, high-integrity aviator who works exceptionally well with people and commands the respect of a hangar floor.

Mandatory Criteria:

• Proven Leadership Background: Previous experience serving explicitly as an Assistant Chief Pilot, Base Lead, or Chief Pilot managing an aviation operation of at least 10+ pilots is mandatory.

• Part 135 Expertise: Minimum of 3 years of previous direct Part 135 operational experience as a pilot/ leader.

• Certifications & Medical: Must hold an FAA Commercial or ATP certificate with appropriate ratings, along with a valid FAA 1st Class Medical Certificate (required for line and training flights).

• Personality Profile: Must be highly charismatic, relatable, and genuinely passionate about mentoring young, early-career pilots. Strong conflict-resolution and interpersonal communication skills are vital.

Preferred Strengths:

• Certified Flight Instructor (CFI/CFII/MEI) background or previous experience as a Check Airman / Check Pilot is highly preferred and will fast-track your application.

Apply with [Company]

[Company] is proud to partner with this elite aviation trailblazer to find a world-class mentor and leader for the Northeast base. If you are ready to secure a stable Monday-to-Friday management schedule, run a massive 38-aircraft footprint, and leave a lasting legacy on the next generation of aviators, this is your moment.