Chief Pilot​/Challenger 604 Pilot in Command; PIC

Position: Chief Pilot/Challenger 604 Pilot in Command (PIC)
Waltzing Matilda Aviation LLC

| 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,…