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Chief Pilot

Job in Kenosha, Kenosha County, Wisconsin, 53142, USA
Listing for: AVIATION ADVISOR INC
Full Time position
Listed on 2026-09-20
Job specializations:
  • Transportation
    Airport Operations & Services
  • Management
    General Management, Airport Operations & Services
Salary/Wage Range or Industry Benchmark: 120000 - 180000 USD Yearly USD 120000.00 180000.00 YEAR
Job Description & How to Apply Below

We are seeking a Chief Pilot to lead and oversee flight operations personnel and training programs. This role is responsible for the overall management, supervision, and leadership of flight operations, with accountability for ensuring that all company flight activities conducted under the Air Carrier Certificate are carried out safely, efficiently, and in full regulatory compliance. The Chief Pilot also plays a critical role in ensuring that the flight department meets its safety management objectives.

In this position, the Chief Pilot will provide strategic leadership and operational oversight for flight crews, including overseeing crew members operating under both
Part 135
and
Part 91
, as well as pilot training, standardization, operating procedures, and safety initiatives, while actively supporting the Company’s Safety Management System (SMS). As a key member of the operational leadership team, the Chief Pilot will work closely with the Director of Operations, Director of Maintenance, Safety Manager, and executive leadership to drive operational excellence and maintain the highest standards of safety, regulatory compliance, and crew performance.

Essential Duties and Responsibilities Flight Operations Leadership

Organize, staff, supervise, and direct all flight operations conducted by the Company.

Provide leadership and oversight of all flight department personnel.

This position requires regular flight duties, and the successful candidate is expected to actively serve as a line pilot while fulfilling Chief Pilot administrative responsibilities. The percentage of time spent flying will vary based on operational needs.

Serve as PIC on scheduled and/or charter flights as assigned.

Exercise limited operational control authority over Air Carrier Certificate as authorized by the Director of Operations.

Manage operational functions that directly impact operational control and flight safety.

Promote a culture of professionalism, accountability, safety, and operational excellence.

Ensure flight operations are conducted safely, efficiently, and in accordance with company standards.

Training Program Management

Organize, administer, and oversee all pilot training programs.

Ensure compliance with FAA-approved training requirements and company training standards.

Coordinate initial, recurrent, upgrade, differences, and special-emphasis training.

Maintain pilot qualification, certification, and training records.

Monitor pilot proficiency and operational performance.

Ensure all flight crew members maintain required qualifications and currency.

Conduct or oversee line checks, standardization evaluations, and operational observations.

Safety Management Systems (SMS)

Actively support and promote the company’s Safety Management System.

Ensure personnel under his or her authority actively participate in safety reporting and SMS activities.

Validate, investigate, and address identified safety risks and safety-risk management deficiencies in a timely and effective manner.

Ensure all operational processes and procedures incorporate applicable risk mitigation measures identified through the Safety Management System.

Participate in Safety Review Board meetings and safety committees.

Promote a Just Culture environment that encourages hazard identification and voluntary safety reporting.

Support organizational learning through analysis of safety reports, operational data,and trend monitoring.

Flight Standards and Standardization

Develop, implement, and maintain aircraft checklists and Standard Operating Procedures (SOPs).

Ensure compliance with the General Operations Manual, Training Manuals, SOPs, and company policies.

Maintain consistency and standardization across all aircraft types and flight crews.

Review operational practices and…

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