Chief Pilot – Milwaukee

Air Cargo Carriers
June 23, 2022
4940 S Howell Ave, Milwaukee, Wisconsin
Job Type


Under general supervision of the Director of Operations the Chief Pilot is responsible for the management of all flight and pilot activities.  


 The following is an overview: 

  •  Direct and supervise all pilot recruitment, interviewing, testing and final selection of pilots including upgrade training as coordinated with the Director of Operation.  Responsible for ensuring Human Resources has completed FAA required pre-employment and pilot background checks.
  • Responsible, directs and coordinates training of all pilots and ensures crewmember proficiency.
  • Oversight and supervision of the Training department including the director of training and staff.
  • Oversight and supervision the Flight following department (Dispatch) directs and coordinates crew scheduling, tracking and check ride activities. 
  • Responsible for the oversight and supervision of all flight crewmembers conducting their duties.
  • Disseminate information to all crewmembers pertaining to routes, airports, navigation aids, company policies and regulations. Ensures that all aircraft are properly equipped for applicable flight operations.
  •  Brief aircrews on operational and theater specific conditions.
  • Responsible for maintaining proficiency records, pilot files, flight schedules, duty time records, reports and correspondence pertaining to flight operations.
  • Monitor compliance with FAR’s and the company policies with regard to all flight crew operations, and dispatch.
  • Develop, update and audit Flight Operations Manual, Standard Operating Procedures and Training manuals as necessary.  This includes but is not limited to company policy and procedures.
  • Evaluate department structure and plan for continual improvement of the efficiency and effectiveness of the team and provide individuals with professional and personal growth.
  • Maintains proficiency as pilot in command and instructor pilot.
  • Ensures all policies/procedures included in the Flight Operations Manual are followed.
  • Tracks and reports fleet reliability and flight time averages to ensure maximum utilization.
  • Writes, reviews, update budget and maintain fiduciary responsibility to the company.
  • Assist company growth.
  • Liaison with FAA
  • Perform all necessary supervisory functions to effectively manage assigned personnel. 

Education Requirements

Minimum Education

  • Associates Degree Bachelor's Degree preferred



  • ATP   

Experience Requirements

Minimum Experience:        

  • 3 years experience
  • Minimum/2500 Hours Flight Experience Minimum/500 Hours Part 135/121 Flight Experience 


Preferred Experience:

  • Up to 5 years experience
  • Minimum/5000 Hours Flight Experience
  • Minimum/1000 Hours Part 135/121 Flight Experience
  • Experience as Chief Pilot or Director of Operations
  • Excellent written and verbal communication skills
  • Strategic thinking
  • Analytical and problem-solving skills
  • Independent decision-making skills 



Machine Skills:

Calculator, PC, telephone, fax machine  


Working Conditions:         

Indoor outdoor, all weather conditions, periods of long sitting.  Must be able to work all shifts as needed. Travel about 20-25% of the time.

Physical Strength:                 

Ability to load cargo, lifting up to 75 lbs. 


Vision Requirements:         

Correctable to 20/20 



Communicate effectively with others in the work environment and external customers 



Represent the company in a professional and positive manner 



Exchange information with others in the work environment and external customers  



Direct – Dispatch Manager & Director of Training - Indirect- N/A  

The above statements are intended to describe the general nature and level of work being  performed.  They are not intended to be construed as an all inclusive list of all responsibilities and skills required for the position.  Nothing in this job description restricts Management’s right to assign or reassign duties and responsibilities.

We are an equal opportunity employer and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, including sexual orientation and gender identity or expression, national origin, disability status, protected veteran status, or any other characteristic protected by law.   

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