10 February 2026

flyExclusive | C208 Chief Pilot

United States

Caravan Chief Pilot - Miami, Florida

Position Type: Full Time

Job Summary and Objective

The Chief Pilot is responsible for directing the operation of the flight department's airline pilots. This role is critical in ensuring operational excellence, safety, and regulatory compliance within the flight department.

Essential Functions

  • Conducts indoctrination and refresher training for pilots.
  • Reviews and forwards pilot performance reports to the Federal Aviation Administration (FAA).
  • Addresses operational and personal issues with subordinates to enhance morale and efficiency.
  • Studies technical manuals and government regulations to ensure company training manuals are compliant and adapted to aircraft types.
  • Represents the company in advisory capacities during contract negotiations with the pilots' union.
  • Accompanies flights to observe pilot performance.
  • Conducts training classes on emergency procedures and survival equipment.
  • Directs the preparation of flight-crew schedules and personnel assignments.
  • Interviews and hires flight personnel.
  • Pilots aircraft on scheduled flights as needed.
  • Conducts or supervises all flight crew personnel training activities.
  • Advises the Director of Operations regarding flight crew personnel training.
  • Assists the Director of Operations in formulating, coordinating, and implementing operations policies and training.
  • Ensures aircraft are properly equipped for applicable operations.
  • Disseminates information to crewmembers regarding routes, airports, NOTAMs, NAVAIDs, company policies, and regulations.
  • Maintains proficiency as Pilot-in-Command.
  • Establishes and leads company operational best practices and the safety review panel.
  • Schedules flight crewmembers and assigns Pilot-in-Command duties.
  • Prepares and maintains proficiency records, pilot files, flight schedules, duty time records, reports, and correspondence.
  • Submits all flight personnel reports to the Director of Operations.
  • Maintains current aircraft copies of the Operations Manual.
  • Ensures all flight crew personnel are certified and supervised according to Federal Aviation Regulations.
  • Assists the Director of Operations in exercising operational control of flight activities.
  • Delegates functions while retaining ultimate responsibility.
  • Holds authority to apply for and receive Operations Specifications Parts A, B, C, D, and E.
  • Serves as the Twelve-Five Standard Security Program (TFSSP) alternate Aircraft Operator Security Coordinator (AOSC).
  • Ensures Aircraft Flight Manuals are maintained in a current manner.
  • Conducts audits of Pilot Training Records and Pilot Duty Records.
  • Monitors and reviews pilot training programs for effectiveness.
  • Conducts periodical reviews of International Training programs, manuals, and/or ARINC policies and procedures for FAA/ICAO compliance.
  • Performs other assignments as deemed appropriate by the Director of Operations.
  • Meets the requirements of 14 CFR 119.69(d) and 119.71.

Skills and Abilities

  • Positive attitude and strong representation of company core values.
  • Self-starter with high motivation and initiative.
  • Strong interpersonal and communication skills (oral and written).
  • Effective time management.
  • Attention to detail.
  • Focus on excellence.
  • Adaptability.
  • Accountability and ability to have difficult conversations.
  • Excellent leadership and training capabilities.
  • Ability to work under pressure with accuracy, efficiency, and confidence.
  • Proficiency in Microsoft Office Suite (Outlook, Teams, Excel, etc.).
  • Exceptional critical thinking, communication, and presentation skills.
  • Ability to multi-task, prioritize, and manage time effectively.
  • Flexibility to work variable shifts, including weekends and holidays.

Other Cognitive Processing

  • Memorization
  • Reasoning and connecting ideas
  • Quick learning
  • Problem identification and solving
  • Multi-tasking
  • Detail orientation

Competencies

  • Microsoft Office Suites

Supervisory Responsibilities

  • Pilots

Work Environment

  • Exposure to loud noises from airplane machinery and jet engines.
  • Typical outdoor and industrial/hangar environments.

Physical Demands

  • Ability to see and hear clearly.
  • Ability to read, comprehend, and speak English clearly.
  • Ability to climb, twist, bend, crouch, stoop, kneel, and crawl.
  • Ability to move in tight quarters.
  • Ability to sit, stand, and walk for extended periods.
  • Ability to work in all weather conditions as needed.
  • Ability to regularly push/pull up to 70 pounds.
  • Ability to regularly lift/move up to 50 pounds.

Dress Code and Uniform

  • Well-groomed appearance.
  • Adherence to department dress code.

Travel Required

Must be local to Miami, Florida (Home Base: TMB).

Qualifications

Required Education and Experience

  • Minimum of 3 years previous experience as a pilot-in-command in Part 135 operations within the 6 years preceding position.
  • A minimum of 2,500 hours total flight time and at least 500 hours of turbine PIC time in a Part 135 environment.
  • Minimum of 3 years of experience operating the Cessna Caravan C208, with both land and seaplane experience required.
  • Free of any documented flight violations, mishaps, or incidents in the past 10 years.
  • Current FAA Medical Certificate (1st class).
  • FAA Certificate (Commercial Pilot with Instrument Rating).
  • Must be authorized to work lawfully in the United States; must provide two forms of Federal Identification.
  • Candidates must successfully complete a comprehensive background check prior to employment.

Preferred Education and Experience

  • Bachelor's degree in aviation or equivalent industry experience.
  • Experience as a check airman is preferred, but candidates with significant Seaplane Flight Instructor time will be considered.
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