Chief Pilot/Challenger 604 Pilot in Command (PIC)

Waltzing Matilda Aviation LLC

wmaviation.com  |  Hanscom AFB (Bedford, MA)

Chief Pilot / Challenger 604 PIC

Full-Time  •  FAR Part 135 / Part 119  •  Compensation: Up to $280,000

Position Summary

Waltzing Matilda Aviation (WMA) is seeking an experienced aviation professional to serve as Chief Pilot and Challenger 604 PIC. This combined role carries the regulatory responsibilities of a Part 119 Director of Operations / Chief Pilot alongside the line flying duties of a full-time Captain on the Challenger 604. The ideal candidate brings strong operational leadership, sound regulatory judgment, and an uncompromising commitment to safety. Compensation is up to $260,000 depending on experience.

Organizational Structure

Reports To: Director of Operations / CEO

Direct Reports: WMA Flight Crew

Base: Hanscom AFB (Bedford, MA)

Key Responsibilities

Part 119 Chief Pilot Duties

• Serve as the FAA-designated Chief Pilot under WMA’s Part 135 Operating Certificate, ensuring full regulatory compliance across all flight operations.
• Develop, maintain, and enforce WMA’s General Operations Manual (GOM), training programs, and standard operating procedures (SOPs).
• Oversee pilot qualification, recurrent training, proficiency checks, and currency requirements in coordination with the Director of Operations.
• Act as liaison with the FAA Principal Operations Inspector (POI) and manage certificate-related correspondence and audits in coordination with the Director of Operations.
• Assist the Director of Safety in safety management system (SMS) initiatives; investigate incidents and implement corrective actions.
• Review and approve flight schedules, crew pairings, duty/rest compliance, and waiver requests.
• Assist the Director of Operations with pilot hiring, onboarding, performance evaluations, and disciplinary processes.
• Monitor regulatory changes (FARs, ACs, NOTAMs) and ensure timely policy updates.
• Coordinate with Maintenance, Dispatch, and Charter Sales to ensure airworthy, legal, and customer-ready operations.
• Perform Check Airman duties for company 135.293 and 135.299 checks as required for the Challenger 604 pilots.

Challenger 604 PIC Duties

• Serve as Pilot-in-Command on the Challenger 604 for Part 91 Owner flights and charter flights operating under FAR Part 135.
• Conduct thorough preflight planning including weather, NOTAMs, fuel, alternates, customs/international requirements, and passenger briefings.
• Ensure all flights comply with WMA SOPs, the Approved Airplane Flight Manual, and applicable FARs.
• Maintain and complete all required flight logs, trip sheets, and regulatory documentation accurately and on time.
• Provide exceptional, professional service to WMA’s charter guests while upholding safety as the highest priority.
• Mentor and develop First Officers and junior crew members.
• Perform other duties as assigned in support of safe and efficient aircraft operations.

General Requirements

• FAA Airline Transport Pilot (ATP) Certificate – Multi-Engine Land
• Bombardier CL-604 Type Rating
• Current FAA First Class Medical Certificate
• FCC Radiotelephone Operator’s Permit
• All Part 119.71(c) requirements to be eligible for Chief Pilot assignment
• At least 23 years of age
• High school diploma or GED (college degree preferred)
• Must pass a 10-year background check and FAA Drug and Alcohol Program testing
• Legal authorization to work in and travel in/out of the United States without restriction
• Ability to lift items weighing up to 50 pounds

Flight Time Requirements

• Minimum 3000 hours total documented flight time
• Minimum 500 hours turbine time
• Minimum 250 hours PIC time in type

When evaluating applicants, consideration will be given to quality, quantity, recency, and verifiability of training; aircraft complexity; types of flight operations; and turbine PIC hours.

Preferred Qualifications

• Prior experience as a Part 119 Chief Pilot or Assistant Chief Pilot
• International flight experience
• College degree in Aviation, Aeronautical Science, or a related field
• Strong working knowledge of FAR Parts 91, 119, and 135
• Experience with SMS development and implementation

Compensation & Benefits

Salary: Up to $280,000 depending on experience

• 401(k) with company match
• Full benefits eligible role (medical, dental, vision, disability)
• Loss of License coverage – fully covered by employer
• Minimum monthly guaranteed days off
• Company AMEX for all business expenses
• Exceptional quality of life with a professional, safety-focused team

About Waltzing Matilda Aviation

Waltzing Matilda Aviation LLC (WMA) is an FAA-licensed Part 135 private jet charter operator based in the Boston area. WMA began Part 91 operations in June 2008 and has accumulated thousands of hours of safe, reliable flying. We own and operate our own aircraft as well as managed aircraft, and we believe in utilizing the latest technology to support the safest operations possible.

Our pilots practice “Safety Always” in every aspect of their work. We inspire air travel by keeping our promises to guests and team members, and we build loyalty through our core values of Safety, Convenient Service, and Reliability. Come take off with us.

Equal Opportunity Employer

WMA is committed to providing equal employment opportunities to all qualified individuals without regard to race, color, religion, sex, national origin, age, disability, sexual orientation, gender identity, genetic information, or any other protected characteristic as outlined by applicable laws. All employment decisions are based on merit, qualifications, and job-related factors. Reasonable accommodations are available for individuals with disabilities – please contact our Human Resources department.