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Contract Air Pilot Jobs (NOW HIRING)

Sherpa Air

Chief Pilot

Job Type Full-time Description The Chief Pilot is responsible for Sherpa Air flight operations to ... contract regulations * Ensures that flights are manned by technically competent and legally ...

New

Sherpa Air

Chief Pilot

Scottsdale, AZ · On-site

The Chief Pilot is responsible for Sherpa Air flight operations to include overall compliance ... contract regulations * Ensures that flights are manned by technically competent and legally ...

New

Blue Air Training

Pilot

North Las Vegas, NV · On-site

Pilot will operate company owned aircraft, including: OV-10 Bronco, PC-9, IAR-823 Brasov, Bell-206 ... Air-Support on another DoD contract. Recency requirement may be waived on a case-by-case basis ...

Textron

Pilot - Skillbridge

Cherry Point, NC · On-site

Air Force Contracts: Conduct flight operations from any of ATAC's permanent facilities (Eglin AFB ... Act as, or support the individual responsible for, pilot Scheduling, Training, NATOPS/Standards ...

Textron

Air Force Contracts: Conduct flight operations from any of ATAC's permanent facilities (Eglin AFB ... Act as, or support the individual responsible for, pilot Scheduling, Training, NATOPS/Standards ...

RAVN Aerospace

Pilot

Houston, TX

... contracts. The ideal candidate will possess a strong background in military tactical flying, particularly in ADAIR (Adversary Air) and Contracted Close Air Support (CCAS). This role will involve ...

RAVN Aerospace

Pilot

San Antonio, TX

... contracts. The ideal candidate will possess a strong background in military tactical flying, particularly in ADAIR (Adversary Air) and Contracted Close Air Support (CCAS). This role will involve ...

RAVN Aerospace

Pilot

San Antonio, TX · On-site

... contracts. The ideal candidate will possess a strong background in military tactical flying, particularly in ADAIR (Adversary Air) and Contracted Close Air Support (CCAS). This role will involve ...

RAVN Aerospace

Pilot

Houston, TX · On-site

... contracts. The ideal candidate will possess a strong background in military tactical flying, particularly in ADAIR (Adversary Air) and Contracted Close Air Support (CCAS). This role will involve ...

Blue Air Training

Pilot (Part-Time)

North Las Vegas, NV · On-site

Pilot will operate company owned aircraft, including: OV-10 Bronco, PC-9, IAR-823 Brasov, Bell-206 ... Air-Support on another DoD contract. Recency requirement may be waived on a case-by-case basis ...

Blue Air Training

Pilot (Part-Time)

Fort Smith, AR · On-site

Pilot will operate company owned aircraft, including: OV-10 Bronco, PC-9, IAR-823 Brasov, Bell-206 ... Air-Support on another DoD contract. Recency requirement may be waived on a case-by-case basis ...

Blue Air Training

Pilot (Part-Time)

Avon Park, FL · On-site

Pilot will operate company owned aircraft, including: OV-10 Bronco, PC-9, IAR-823 Brasov, Bell-206 ... Air-Support on another DoD contract. Recency requirement may be waived on a case-by-case basis ...

Textron

Pilot - Skillbridge (High Point)

High Point, NC · On-site

Air Force Contracts: Conduct flight operations from any of ATAC's permanent facilities (Eglin AFB ... Act as, or support the individual responsible for, pilot scheduling, training, NATOPS/Standards ...

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Contract Air Pilot information

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$49.5K

$130.9K

$201K

How much do contract air pilot jobs pay per year?

As of Aug 7, 2026, the average yearly pay for contract air pilot in the United States is $130,916.00, according to ZipRecruiter salary data. Most workers in this role earn between $100,000.00 and $155,000.00 per year, depending on experience, location, and employer.

What is a contract air pilot?

Contract Air Pilots are professional pilots who are hired on a temporary or per-assignment basis, rather than as full-time employees. They may operate a variety of aircraft, including private jets, cargo planes, or helicopters, depending on the needs of their clients. Contract Air Pilots often work for multiple employers, such as private individuals, corporations, or charter companies, and may be responsible for their own licensing, training, and insurance. This flexible arrangement allows both pilots and employers to meet short-term or specialized aviation needs. Contract pilots must comply with the same safety and regulatory standards as full-time pilots.

What are the key skills and qualifications needed to thrive as a contract air pilot?

To thrive as a Contract Air Pilot, you need a commercial pilot license, comprehensive flight experience, and up-to-date medical certification. Familiarity with various aircraft, flight management systems, and navigation tools is essential, and additional type ratings or instrument ratings are often required. Strong situational awareness, decision-making, and communication skills are crucial for handling dynamic flight conditions and coordinating with ground teams. These competencies ensure safety, regulatory compliance, and efficient operations in a role that often demands flexibility and adaptability.

What are some common challenges contract air pilots face when transitioning between different employers or flight operations?

Contract Air Pilots often encounter the challenge of quickly adapting to new aircraft types, company procedures, and operational protocols when moving between employers or assignments. Each organization may have unique safety standards, communication practices, and scheduling systems, requiring pilots to be highly adaptable and detail-oriented. Building rapport with new crew members and understanding the expectations of different flight departments are also essential for maintaining smooth operations and ensuring safety. Staying current with certifications and regulatory requirements across various jurisdictions can further add complexity to the role.

What is the difference between Contract Air Pilot vs Commercial Pilot?

AspectContract Air PilotCommercial Pilot
CredentialsCommercial Pilot Certificate, possibly additional type ratingsCommercial Pilot Certificate, multi-engine ratings often required
Work EnvironmentCharter services, private contracts, on-demand flightsAirlines, charter companies, cargo carriers
Employer & IndustryPrivate clients, companies offering specialized flight servicesAirlines, freight, tourism

Contract Air Pilots typically operate on a freelance basis, providing specialized or on-demand flight services for private clients or companies. Commercial Pilots work for airlines or commercial operators, often with more structured employment. Both roles require a Commercial Pilot Certificate, but Contract Air Pilots often have more flexibility and varied work environments.

More about Contract Air Pilot jobs
What cities are hiring for Contract Air Pilot jobs? Cities with the most Contract Air Pilot job openings:
What states have the most Contract Air Pilot jobs? States with the most job openings for Contract Air Pilot jobs include:
What job categories do people searching Contract Air Pilot jobs look for? The top searched job categories for Contract Air Pilot jobs are:
Contract Air Pilot jobs near you
Infographic showing various Contract Air Pilot job openings in the United States as of August 2026, with employment types broken down into 91% Full Time, 7% Part Time, 1% Contract, and 1% Nights. Highlights an 97% Physical, 1% Hybrid, and 2% Remote job distribution, with an average salary of $130,916 per year, or $62.9 per hour.

Chief Pilot

Sherpa Air

Remote

Full-time

Medical, Dental, Vision, Retirement, PTO

Posted yesterday

New

Job description

Job Type
Full-time
Description
The Chief Pilot is responsible for Sherpa Air flight operations to include overall compliance related to scheduling, operations, maintenance coordination and safety procedures. The Chief Pilot is responsible for pilot training, maintenance test and functional flights, pilot records, and operational standards for all pilot personnel operating under FAA Part 135.
Must be able to operate independently in differing environments to include domestic and worldwide. Will interface with government and private sector customers on a daily basis.
Responsibilities:
  • Reports directly to the Director of Operations
  • Enforces operational standards of all company flight operations manuals across all aircraft and ensures compliance by all assigned company pilots
  • Implements and administers company standard operating procedures to ensure the highest standards of safety and quality of service
  • Directs and guides flight operations to ensure they are conducted in accordance with established company practices and procedures and in compliance with applicable government, FAA and contract regulations
  • Ensures that flights are manned by technically competent and legally qualified crew members to include review and approval of all Sherpa Air flight crews
  • Supervises activities and performance of Sherpa Air pilots and provides periodic written evaluations
  • Remains on-call for internal flight requirements supporting company
  • Manages Sherpa Air Dispatchers for domestic and international flights
  • Maintains PIC qualifications on at least one company aircraft
  • Ensures all Sherpa Air-owned or managed aircraft are properly equipped with aeronautical charts, Navigational Aids, etc. required for safe flight through various vendor subscriptions
  • Ensures that all flight crews document aircraft discrepancies and reports equipment malfunctions to appropriate personnel in a timely and accurate manner
  • Maintains records of activities, flight logs and training in accordance with company and FAA regulatory compliance requirements
  • Represents Sherpa Air by supporting our customers and presenting a professional pilot image to customers and the general public.
  • Exhibits a positive attitude and can adapt to change
  • Responsible for all pilots and flight crew personnel assigned to fly Sherpa Air operated aircraft
  • This job may operate in various field locations. This role routinely uses standard office equipment. Travel and deployment could be required.

Requirements
Minimum Qualifications:
  • Bachelor's degree preferred or relevant combination of education and experience
  • Must meet the Part 119 experience requirements listed in FAR 119.71(c)
  • FAA, ATP and Multi-Engine Fixed Wing ratings
  • FAA Class I Medical Certificate
  • Flight time experience: total time of 5,000 hours of which 2,000 must be multi-engine turbine
  • Must have 2,500 hours as PIC
  • Possess a valid US driver's license
  • Capable of lifting at least 50 pounds
  • Possess a current US Passport
  • Able to secure necessary VISA(s)
  • Self-motivated and able to work efficiently without direct supervision
  • Able to receive DoD or DHS SECRET Security clearance if applicable
  • Must be a US citizen
  • Must pass a background check and drug screening

Preferred Qualifications:
  • FAA Certified Flight Instructor (CFl) and/or Certified Flight Instructor Instrument (CFIl)
  • Experience with international flight operations
  • Experience with intemational flight operations NAT North Atlantic High Altitude
  • Hawker 1000 type rating

Background Screening/Check/Investigation:
Successful completion of a background screening/check/investigation will/may be required as a condition of hire.
ADA:
Sherpa Air will make reasonable accommodations in compliance with the Americans with Disabilities Act 1990
EEO/AA:
Sherpa Air does not discriminate based on race, color, national origin, sex, religion age, disability, sexual orientation, gender identity, veteran status, Height, weight, or marital status in employment or the provision of services and is an equal access/opportunity/affirmative action employer.
Benefits:
We offer a competitive benefits package, covering the cost of medical for you and your family; we also offer dental, vision, health and wellness benefits and a generous retirement savings plan. We believe that our employees can manage their workload and their personal life, therefore we extend a generous PTO policy. This allows our employees to balance their lives as they see fit.

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