Lead Captain (PIC) — Challenger 350 | GYY-Based, Chicago Area

Pilot Assessments; Wheeling (IL); On-site; USD 280,000 - 325,000; Full time

Benefits offered by this job

Health insurance

401(k) with company match

Paid time off

Life and disability insurance

Job summary

Pilot Assessments is seeking a highly experienced Challenger 350 captain to lead daily flight readiness, safety, and an extraordinary owner experience in a dynamic, owner-centric setting.

You will manage schedules and communications, coordinate with the regional team, and ensure CFR compliance while mentoring crew members and maintaining peak aircraft readiness at our Wheeling, IL base.

Qualifications

• 4,000 total flight time required.
• 2,000 PIC recommended.
• 1,500 jet / 500 jet PIC.
• 1,000 turbine / 1,000 turbine PIC.
• 1,000 multi-engine / 500 multi-engine PIC.
• 300 instrument time.
• Challenger 350: 500 PIC in type preferred.

Responsibilities

• Serve as the primary contact for Challenger 350 aircraft and trip matters.
• Plan and execute safe, efficient flights under applicable CFRs.
• Manage duty, flight, and rest periods to meet requirements.
• Provide proactive communication on standby assignments and reports.
• Oversee and maintain EFB hardware, apps, and data integrity.
• Ensure navigation charts, publications, and manuals are current.
• Coordinate trip logistics with leadership and concierge team.
• Offer schedule flexibility to support owner needs, including nights/weekends.
• Mentor crew members and uphold Jet Linx values.
• Maintain current medical and make proactive flight decisions.

Skills

Total flight time

PIC experience

Challenger 350 experience

Turbine experience

Instrument rating

First-class medical

Part 142 training

Education

Bachelor’s degree

CAM certification

Tools

EFB hardware

Job description

The Opportunity

Own the standard of excellence for a Challenger 350 operation. You’ll lead daily flight readiness, champion safety and compliance, and deliver a concierge-level experience to our aircraft owner. This is a visible, trusted role for a seasoned captain who thrives in dynamic, owner-focused environments.

What You’ll Do

• Serve as the primary contact for aircraft and trip matters related to the Challenger 350.
• Plan and execute safe, efficient flights in accordance with Federal Aviation Regulations and Jet Linx procedures (Part 91/135).
• Manage duty, flight, and rest periods to meet company and CFR requirements.
• Maintain proactive, timely communication on standby assignments, trip notifications, position calls, and pre-/post-flight reports.
• Oversee and maintain EFB hardware, applications, and data integrity.
• Ensure navigation charts, publications, and company manuals remain current.
• Partner with the Regional Vice President and concierge team to coordinate trip logistics and owner preferences.
• Exercise schedule flexibility to support aircraft and owner needs, including nights, weekends, and holidays.
• Mentor additional crew members, fostering a culture of professionalism aligned with Jet Linx core values.
• Maintain a current first-class medical and apply strong, proactive decision-making in all phases of flight.

What You’ll Bring

• Flight time minimums:
  • 4,000 total time
  • 2,000 PIC
  • 1,500 jet / 500 jet PIC
  • 1,000 turbine / 1,000 turbine PIC
  • 1,000 multi-engine / 500 multi-engine PIC
  • 300 instrument
  • Challenger 350: at least 500 PIC in type
• Training: Initial or recurrent Part 142 training in type within the last 24 months (preferred).
• Credentials: Current first-class medical, valid passport, FCC Restricted Radio Operator License, ability to obtain a U.S. driver’s license, and proof of eligibility to work in the United States.
• Compliance: Pass pre-employment drug screening and participate in random drug and alcohol testing; complete an FAA Pilot Records Database review with a System Chief Pilot.
• Travel: Unrestricted travel to EU, Canadian, and Caribbean countries.
• Education: Bachelor’s degree or equivalent work experience required; CAM certification preferred.
• Location: Live within—or be willing to relocate within—a two-hour call-out of the home base.
• Work environment: Frequent work around aircraft/terminals; ability to move up to 50 pounds regularly.

Pay & Benefits

• Base salary: $280,000 – $325,000 annually (commensurate with location, aircraft size, education, training, and experience)
• Health: Medical, dental, and vision insurance
• Retirement: 401(k) with 6% company match
• Time off: Paid time off
• Coverage: Company-paid life and short-term disability

Ready to Lead?

If you’re a high-time Challenger 350 captain who leads by example, communicates with clarity, and delivers a best-in-class owner experience, we’d love to connect.