Challenger 300/350 Captain (Pilot in Command) – Chicago/Wheeling, IL

Pilot Assessments; Wheeling (IL); On-site; USD 180,000 - 240,000; Full time

Benefits offered by this job

Health, dental, and vision insurance

401(k) with company match

Paid time off

Company-paid life insurance

Company-paid short-term disability

Job summary

Pilot Assessments is seeking a highly experienced Pilot in Command to lead safe and compliant flight operations. You will exercise PIC authority, plan and brief trips, and ensure duty, flight, and rest compliance across CFRs and company procedures.

You will maintain readiness, manage EFB systems, demonstrate decisive leadership, keep medical and qualifications current, and support professional crews on every flight. Join a team that values safety, service, and operational excellence.

Qualifications

• 3,500 hours total time.
• 2,000 hours PIC (incl. 250 PIC in Challenger 300/350).
• 1,500 jet hours (incl. 500 jet PIC).
• 1,000 turbine hours (incl. 1,000 turbine PIC).
• 1,000 multi-engine hours (incl. 500 multi-engine PIC).
• 300 instrument hours.
• Initial or recurrent Part 142 training in type within past 24 months preferred.
• ATP eligibility; First Class Medical; valid US driver’s license; passport; FCC Restricted Radio License.
• Authorization to work in the United States; travel to EU, Canada, Caribbean destinations.
• Willing to complete drug screening and FAA PRBD review.
• Availability for nights, weekends, holidays; two-hour call-out radius or willing to relocate.
• Bachelor’s degree or equivalent work experience.
• Physical ability to move up to 50 lbs around aircraft and terminals.

Responsibilities

• Exercise Pilot in Command authority to ensure safe, compliant, and efficient flight operations in accordance with FARs and Jet Linx procedures.
• Plan, brief, and execute trips while managing duty, flight, and rest periods under company and CFR requirements.
• Remain mission-ready: maintain communication for standby assignments, trip notifications, position calls, and timely pre-/post-flight reports.
• Steward your EFB: maintain hardware, applications, and ensure navigation charts, publications, and company manuals are current.
• Demonstrate strong, proactive decision-making and professional crew leadership on every flight.
• Maintain a current First Class Medical Certificate and all required qualifications and records.

Skills

Total time

PIC hours

Jet hours

Turbine hours

Multi-engine hours

Instrument hours

Education

Bachelor's degree or equivalent

Job description

What you'll do

• Exercise Pilot in Command authority to ensure safe, compliant, and efficient flight operations in accordance with FARs and Jet Linx procedures.
• Plan, brief, and execute trips while managing duty, flight, and rest periods under company and CFR requirements.
• Remain mission-ready: maintain communication for standby assignments, trip notifications, position calls, and timely pre-/post-flight reports.
• Steward your EFB: maintain hardware, applications, and ensure navigation charts, publications, and company manuals are current.
• Demonstrate strong, proactive decision-making and professional crew leadership on every flight.
• Maintain a current First Class Medical Certificate and all required qualifications and records.

What you bring

• Flight experience minimums:
  • 3,500 hours total time
  • 2,000 hours PIC (including 250 hours PIC in Challenger 300/350 type)
  • 1,500 jet hours (including 500 jet PIC)
  • 1,000 turbine hours (including 1,000 turbine PIC)
  • 1,000 multi-engine hours (including 500 multi-engine PIC)
  • 300 instrument hours
• Training & currency: Initial or recurrent Part 142 training in type within the past 24 months preferred.
• Certificates & documents: Ability to obtain an ATP; current First Class Medical; valid U.S. driver's license; current passport; FCC Restricted Radio License.
• Eligibility & travel: Proof of authorization to work in the United States; unrestricted ability to travel to EU, Canadian, and Caribbean destinations.
• Compliance: Willing to complete required drug screening and random testing; authorize and pass an FAA Pilot Records Database review with a System Chief Pilot.
• Schedule & lifestyle: Availability for nights, weekends, and holidays; residence within a two-hour call-out of base (or willingness to relocate).
• Education: Bachelor's degree or equivalent work experience.
• Physical demands: Comfortable working in/around aircraft and terminals; able to frequently move up to 50 lbs.

Benefits & rewards

• Comprehensive health, dental, and vision insurance
• 401(k) with 6% company match
• Paid time off
• Company-paid life insurance
• Company-paid short-term disability

Ready to captain your next chapter?

Bring your Challenger 300/350 expertise to a team that values safety, professionalism, and service excellence. If you meet the requirements above and are ready to fly, we'd love to hear from you.