About This Role
Aviation Advisor, Inc. is seeking a Chief Pilot in Kenosha, Wisconsin, to lead and oversee flight operations personnel, training programs, safety initiatives, and operational compliance. The role combines administrative leadership with regular line-pilot duties, including serving as Pilot-in-Command on scheduled and charter flights when assigned. The Chief Pilot will oversee crews operating under Parts 135 and 91, support the company Safety Management System, maintain standardization across the fleet, prepare the operation for FAA and industry audits, and work closely with operations, maintenance, safety, training, and executive leadership.
Duties & Responsibilities
- The Chief Pilot organizes, staffs, supervises, and directs company flight operations and provides leadership for all flight-department personnel while continuing to fly regularly as operational needs require. Duties include serving as PIC on scheduled and charter flights, exercising limited operational-control authority as authorized by the Director of Operations, managing functions affecting flight safety, and promoting professionalism, accountability, safety, and operational excellence. The role administers initial, recurrent, upgrade, differences, and special-emphasis training
- maintains qualification, certification, and training records
- monitors pilot proficiency
- ensures crew currency
- and conducts or oversees line checks, standardization evaluations, and operational observations. The Chief Pilot supports the SMS by promoting safety reporting and Just Culture, investigating and addressing safety risks, applying risk-mitigation measures, participating in safety-review meetings, and analyzing safety reports, operational data, and trends. Additional responsibilities include developing and maintaining checklists and SOPs, ensuring compliance with the GOM, training manuals, SOPs, FAA regulations, operations specifications, and company policies, maintaining readiness for FAA inspections and audits, supporting WYVERN, IS-BAO, and ARGUS compliance, completing corrective actions, distributing aeronautical and operational information, coordinating with vendors and training providers, and leading hiring, onboarding, evaluations, professional development, welfare, conduct, retention, and succession-planning initiatives for flight personnel.
Requirements
- Required qualifications include meeting all FAA qualifications for a Chief Pilot under 14 CFR Part 119
- holding a valid Airline Transport Pilot Certificate for the category of aircraft operated by Aviation Advisor, Inc.
- holding a current FAA First-Class Medical Certificate
- and being qualified under the company's approved training program to serve as Pilot-in-Command on at least one company-operated aircraft. The posting also requires knowledge of FAA Parts 91, 119, and 135, Safety Management Systems, operational-control principles, and Crew Resource Management, together with demonstrated leadership, communication, organizational, problem-solving, and decision-making skills. BART experience is identified as preferred. Additional preferred qualifications include previous FAA-approved Chief Pilot experience
- experience with WYVERN, IS-BAO, and Safety Management Systems
- experience conducting pilot evaluations, line checks, and standardization programs
- a bachelor's degree in aviation, business, management, or a related field
- and CFI, CFII, and MEI credentials. The position requires the ability to perform duties as a flight crewmember, maintain FAA medical certification, travel as needed, work in airport and aviation environments, and respond to operational matters outside normal business hours.