Chief Pilot

Aviation Advisor, Inc.; Kenosha (WI); On-site; USD 180,000 - 240,000; Full time

Job summary

Aviation Advisor, Inc. in Kenosha, WI seeks a Chief Pilot to lead flight operations, training, SMS, and regulatory compliance under the Air Carrier Certificate.

The role combines executive oversight with active line pilot duties to support safe, efficient flight operations. You will organize and supervise flight department personnel, maintain training records, oversee audits, and ensure SOPs and manuals meet FAA standards.

Qualifications

• Meets FAA qualifications for Chief Pilot under 14 CFR Part 119.
• Holds ATP certificate for the operator’s aircraft category.
• Current FAA First-Class Medical Certificate.

Responsibilities

• Lead and direct all flight operations and certify safe, compliant performance.
• Oversee pilot training programs; ensure FAA-approved training and records.
• Maintain and enforce SOPs, checklists, and regulatory compliance programs.
• Oversee safety management system activities and safety reporting.

Skills

Strategic leadership

Safety culture

Regulatory knowledge

Communication

Education

Bachelor’s degree in aviation/related field

Tools

WYVERN

IS-BAO

CRM

Job description

Position Summary

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.

Pilot

Kenosha WI

Full-time

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
• Air Carrier Operations Specifications
• 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:
• WYVERN
• 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 as Pilot-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.
• Strog 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.

Work Environment

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.

Exempt Status

Exempt

EOE Statement

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.