Chief Pilot

AVIATION ADVISOR INC; Kenosha, Northern (WI, KY); Hybrid; USD 120,000 - 180,000; Full time

Job summary

Aviation Advisor, Inc. is seeking a Chief Pilot to lead and oversee all flight operations personnel, training programs, and SMS initiatives. This leadership role requires active line flying as PIC when needed and ongoing regulatory compliance across Part 135 and Part 91 operations.

The Chief Pilot will collaborate with the Director of Operations and Safety Manager to maintain top safety standards, standardize procedures, and manage crews across multiple aircraft in a dynamic aviation environment.

Qualifications

• Meets all FAA qualifications for Chief Pilot under 14 CFR Part 119.
• ATP certificate for the category of aircraft operated by the company.
• Current FAA First-Class Medical Certificate.
• Qualified to serve as PIC on at least one aircraft.
• FAA Parts 91, 119, and 135 familiarity.

Responsibilities

• Lead and supervise all flight operations staff.
• Oversee pilot training programs and standards.
• Maintain Safety Management System and promote a Just Culture.
• Develop and enforce SOPs and standard checklists.
• Ensure regulatory compliance and readiness for FAA inspections.
• Serve as PIC when required and fly as needed.
• Collaborate with operations, maintenance, and leadership to drive excellence.

Skills

Leadership

Safety management

Regulatory compliance

Communication

Education

Bachelor’s degree in aviation, business, or related field

CFI, CFII, and MEI

Tools

WYVERN

IS-BAO

Flight Ops Software

Job description

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 bothPart 135andPart 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 withcompany 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 operationalobservations.

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 OperatingProcedures (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 implement improvements that enhance safety and efficiency.

Ensure flight crews remain informed of changes to regulations, operational procedures, and company standards.

Regulatory Compliance

Ensure flight operationsand relatedactivities are conducted incompliance with:

FAA Regulations

Company General Operations Manual (GOM)

Safety Management System requirements

Applicable industry standards and best practices

Maintain readiness forFAA inspections, audits, and regulatory reviews.

Support compliance with industry accreditation standards including:

IS-BAO

ARGUS

Ensure corrective actions resulting from audits or inspections are completedeffectively andon schedule.

Operational Communications

Receive, review, and take appropriate action regarding aeronautical information affecting the safety of flight operations

Disseminate operational and safety-related information to flight crews and operational personnel

Ensure timely communication of changes to regulations, procedures, manuals, notices, and company policies

Serve as a liaison with external vendors, training providers, regulations, and organizations that may affect flight operations.

Personnel Leadership and Welfare

Provide leadership, mentorship, and professional development opportunities for flight department personnel.

Oversee the welfare, performance, and professional conduct of pilots and flight operations personnel.

Participate in hiring, onboarding, evaluations, disciplinary actions, and retention initiatives.

Foster a positive and collaborative working environment.

Support succession planning and long-term pilot development initiatives.

Required Qualifications

Meets all FAA qualifications for ChiefPilot under 14CFRPart119.

Holds a valid Airline Transport Pilot (ATP) Certificate for the category of aircraft operated by the Aviation Advisor, Inc.

Holds a current FAAFirst-Class Medical Certificate.

Qualified inaccordance with the Company’s approved training program to serve asPilot-in-Command on at least one aircraft operated by Company.

FAA Parts 91, 119, and 135

Safety Management Systems (SMS)

Operational Control principles

Crew Resource Management (CRM)Demonstrated leadership, communication, and organizational skills.

Strong problem-solving and decision-making abilities.

BART experience preferred

Preferred Qualifications

Previous FAA-approved Chief Pilotexperience.

Experience with WYVERN, IS-BAO, and Safety ManagementSystems.

Experience conducting pilot evaluations, line checks, and standardization

programs.

Bachelor’s degree in aviation, Business, Management, or a related field.

CFI, CFII, and MEI

Physical Requirements

Ability to perform dutiesas a required flightcrewmember.

Ability to maintainFAAmedical certification requirements.

Ability to travel as required.

Ability to sit, stand, walk, climb aircraftstairs,and work inairport and aviation environments.

Ability to respond to operational matters outside normal business hours.

The Chief Pilotoperatesin a dynamic aviation environment that requires regular interactionwith flightcrews, maintenance personnel,schedulers, regulators, auditors, customers,and executive leadership. This position requires flexibilityand availability to support operational and safety needs beyond traditional business hours.

Compensation

The salary will be determined based on factors such as the candidate's experience, geographic location, and other relevant considerations.

Aviation Advisor, Inc. is an equal opportunity employer that is committed to diversity and inclusion in the workplace. We prohibit discrimination and harassment of any kind based on race, color, sex, religion, sexual orientation, national origin, disability, genetic information, pregnancy, or any other protected characteristic as outlined by federal, state, or local laws.

This policy applies to all employment practices within our organization, including hiring, recruiting, promotion, termination, layoff, recall, leave of absence, compensation, benefits, training, and apprenticeship. Aviation Advisor, Inc. makes hiring decisions based solely on qualifications, merit, and business needs at the time.