Chief Pilot & Flight Ops Strategist

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

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.