Chief Pilot / Head of Flight Instruction Lakeland, FL | Full-Time | $100,000-$140,000 About Kingsky Flight Academy Kingsky Flight Academy is seeking an experienced aviation leader to serve as our Chief Pilot - Head of Flight Instruction . This is a senior leadership position responsible for the overall quality, consistency, and effectiveness of our flight instruction program. This is primarily an administrative leadership role, not a full-time flying position . While occasional flight evaluations, instructor proficiency checks, or instructional flights may be required, the majority of the role is focused on developing instructors, improving training quality, managing student progression, and leading the instructional department. Kingsky currently operates a fleet of 36 aircraft , serves approximately 300 active students , and employs approximately 70 flight instructors . The Chief Pilot provides leadership to this instructional team through Lead Instructors while ensuring a consistent, high-quality training experience for both students and instructors. Success in this role requires someone who enjoys coaching instructors, developing students, solving operational challenges, and building a culture centered on professionalism, accountability, safety, and continuous improvement. The Chief Pilot works closely with the Flight Standards Manager, Scheduling Manager, and Billing Manager as part of the Operations leadership team to ensure students receive an exceptional training experience from enrollment through graduation.

Reports to:

Vice President of Operations Compensation $100,000-$140,000 annual salary , based on experience and qualifications Performance bonus opportunities Medical, Dental, and Vision Insurance (following eligibility requirements) Paid Time Off What You'll Do Flight Instruction Leadership Lead, mentor, and develop Kingsky's flight instructor team through ongoing coaching, standardization, and professional development. Establish and maintain consistent instructional standards while promoting a culture of safety, professionalism, accountability, and continuous improvement. Observe instructors, provide meaningful feedback, and ensure instructional techniques and teaching methods meet Kingsky's expectations. Participate in the hiring, onboarding, mentoring, and performance development of flight instructors. Student Training & Progression Guide students through their flight training programs from start to finish , developing and monitoring training plans that incorporate ground school, flight training, online coursework, written examinations, and other required milestones to improve progression, retention, and training timelines. Track student grades, attendance, flight progress, training milestones, and overall performance , proactively identifying students who are falling behind or encountering obstacles and working with students and instructors to develop appropriate solutions. Conduct and document student progress meetings and prepare reports for leadership discussions regarding performance, training challenges, scheduling, goals, and overall student progress. Coordinate checkride scheduling with Designated Pilot Examiners (DPEs) and work with students and instructors to identify and schedule additional proficiency training when necessary to support checkride readiness. Operational Leadership Collaborate closely with the Flight Standards Manager, Scheduling Manager, and Billing Manager to support student progression and efficient day-to-day operations. Work with Scheduling to balance instructor utilization, student training plans, checkrides, and operational needs. Provide leadership during periods of growth by balancing instructor resources, student demand, and operational priorities. Participate in leadership meetings, using student progression and operational data to identify challenges, recommend solutions, and support strategic planning for the flight training department. Qualifications Required FAA Commercial Pilot Certificate FAA Flight Instructor Certificates (CFI, CFII, and MEI) Valid FAA First or Second Class Medical Certificate Minimum five years of flight instruction experience Extensive experience operating within 14 CFR Part 141 Demonstrated leadership experience managing, mentoring, or developing flight instructors Excellent communication, coaching, organizational, and problem-solving skills Strong administrative skills and proficiency with Microsoft Office and other operational software Preferred Assistant Chief Instructor, Chief Instructor, Check Instructor, or similar leadership experience Experience leading large instructor teams 2,500+ total flight hours 1,200+ hours of dual instruction given 300+ multi-engine flight hours Experience with FAA inspections, audits, and regulatory oversight Knowledge of FAA Order 8900.1, TSA training requirements, Training Course Outlines (TCOs), and Safety Management Systems (SMS) Physical Requirements Reasonable accommodations may be made to enable qualified individuals with disabilities to perform the essential functions of the position. While performing the essential duties of this position, the employee is regularly required to remain in a stationary position while working at a computer; communicate effectively with employees, students, and regulatory representatives; review training records and operational documentation; occasionally move throughout office, classroom, hangar, and ramp areas; and periodically conduct flight evaluations or proficiency flights as required. Work Environment This position is performed primarily in a professional office environment within an active Part 141 flight training operation. While occasional flying is expected to support instructor evaluations or operational needs, the majority of the role is administrative and leadership-focused . The successful candidate should be comfortable analyzing student performance, managing multiple training priorities, conducting student and instructor meetings, and collaborating with department leaders in a large, fast-paced flight training operation. Equal Opportunity Employer Kingsky Flight Academy is an Equal Opportunity Employer. Employment decisions are based on qualifications, merit, and business needs without regard to race, color, religion, sex, national origin, age, disability, protected veteran status, or any other status protected by applicable federal, state, or local law.

Pay:

$100,000.00 - $140,000.00 per year

Benefits:

401(k) Dental insurance Flexible schedule Health insurance Life insurance Paid time off Vision insurance Application Question(s): What is your total flight hours? What is your hours of dual instruction given? How many Multi-Engine flight hours? Do you have experience with FAA inspections, audits, and regulatory oversight? Do you have knowledge with FAA Order 8900.1, TSA training requirements, Training Course Outlines (TCOs), and Safety Management Systems (SMS)?

Education:

High school or equivalent (Required)

Experience:

Flight Instruction:

5 years (Required) operating within 14 CFR Part 141: 1 year (Required)

Assistant Chief Instructor :

1 year (Preferred)

Chief Instructor:

1 year (Preferred)

Check Instructor :

1 year (Preferred)

License/Certification:

FAA Commercial Pilot Certificate (Required) CFI, CFII, and MEI (Required) Ability to

Commute:

Lakeland, FL 33811 (Required)

Work Location:

In person