Chief Pilot & Flight Operations Leader (Part 135/91)

Pilot Assessments; Kenosha (WI); On-site; USD 180,000 - 240,000; Full time

Job summary

Aviation Advisor, Inc. seeks a Chief Pilot to lead flight operations, training, safety initiatives, and compliance across Part 135 and Part 91.

The role includes serving as PIC on scheduled and charter flights and partnering with operations, maintenance, safety, and leadership to drive standardization and readiness for audits. You will oversee training programs, record maintenance, line checks, and performance evaluations while promoting Just Culture and safety across the fleet.

Qualifications

• Demonstrated leadership and supervision across flight operations.
• Experience promoting safety culture and Just Culture.
• Strong knowledge of FAA Part 119/135/91 regulatory frameworks.

Responsibilities

• Serve as Pilot-in-Command on scheduled and charter flights.
• Organize and staff flight operations; mentor flight-department personnel.
• Manage safety and compliance programs; support audits and improvements.
• Develop and maintain checklists and SOPs per FAA and company policies.
• Lead hiring, onboarding, and performance evaluations for flight personnel.
• Coordinate with operations, maintenance, safety, and executive teams.

Skills

Leadership

Communication

Organizational

Problem-solving

Decision-making

Safety culture

Education

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

CFI, CFII, MEI credentials

Tools

WYVERN

IS-BAO

ARGUS

BART

Job description

The Opportunity

As Chief Pilot, you will lead flight operations personnel, training programs, safety initiatives, and operational compliance across Part 135 and Part 91 operations-while serving as Pilot-in-Command on scheduled and charter flights as assigned. You will partner with operations, maintenance, safety, training, and executive leadership to drive standardization, readiness for audits, and continuous improvement.

What You'll Lead & Do

• Serve as Pilot-in-Command (PIC) on scheduled and charter flights when assigned.
• Organize, staff, supervise, and direct company flight operations; provide leadership and mentorship for all flight-department personnel.
• Exercise limited operational-control authority as authorized by the Director of Operations; manage functions affecting flight safety and performance.
• Administer initial, recurrent, upgrade, differences, and special-emphasis training; ensure standardization across the fleet.
• Maintain qualification, certification, and training records; monitor pilot proficiency and crew currency; conduct or oversee line checks, standardization evaluations, and operational observations.
• Support the SMS: promote safety reporting and Just Culture; investigate and mitigate risks; participate in safety-review meetings; analyze safety reports, operational data, and trends.
• Develop and maintain checklists and SOPs; ensure compliance with the GOM, training manuals, SOPs, FAA regulations, Operations Specifications, and company policies.
• Maintain readiness for FAA and industry audits; support compliance with WYVERN, IS-BAO, and ARGUS; complete corrective actions as required.
• Distribute aeronautical and operational information; coordinate with vendors and training providers to optimize training quality and scheduling.
• Lead hiring, onboarding, performance evaluations, professional development, conduct and welfare initiatives, retention, and succession planning for flight personnel.
• Partner closely with operations, maintenance, safety, training, and executive teams to promote professionalism, accountability, safety, and operational excellence.

What You'll Bring

• Meets all FAA qualifications for a Chief Pilot under 14 CFR Part 119.
• Holds a valid Airline Transport Pilot (ATP) certificate for the category of aircraft operated by Aviation Advisor, Inc., and a current FAA First-Class Medical.
• Qualified under the company’s approved training program to serve as PIC on at least one company-operated aircraft.
• In-depth knowledge of FAA Parts 91, 119, and 135, Safety Management Systems, operational-control principles, and Crew Resource Management.
• Demonstrated leadership, communication, organizational, problem-solving, and sound decision-making skills.
• Ability to perform flight crewmember duties, maintain medical certification, travel as needed, work in airport/aviation environments, and respond to operational matters outside normal business hours.

Preferred Qualifications

• Previous FAA-approved Chief Pilot experience.
• Experience with WYVERN, IS-BAO, ARGUS, and SMS.
• Experience conducting pilot evaluations, line checks, and standardization programs.
• Bachelor’s degree in aviation, business, management, or a related field.
• CFI, CFII, and MEI credentials.
• Experience with BART preferred.

Certifications & Licenses

• Required: ATP (unrestricted or restricted, as applicable) and current FAA First-Class Medical.

Role Details

• Base: Kenosha, Wisconsin (U.S.).
• Operations: Part 135 on-demand charter and Part 91 operations.
• Schedule: Flexibility required, including availability outside normal business hours based on operational needs.
• Travel: Travel as needed for operations, training, audits, and vendor coordination.

Aviation Advisor, Inc. is an equal opportunity employer.