Onward
and upward

Milwaukee, WI

Must reside within a one-hour drive of Milwaukee. Relocation benefits are available for the right candidate. 

Jet OUT is seeking a System Chief Pilot to help lead pilot operations across the company and support the continued growth and standardization of our flight department. Reporting to the Director of Operations, the System Chief Pilot serves as a key operational leader responsible for pilot standardization, hiring, pilot development, disciplinary oversight, check pilot functions, FAA interaction, operational policy support, and strengthening culture and accountability across the organization.

The System Chief Pilot will provide leadership across our multi-base operation and directly oversee multiple Base Chief Pilots. We are seeking a leader who is fully bought in, leads with professionalism and accountability, and wants to help build a flight department known for high standards, strong culture, and operational credibility.

The ideal candidate is a strong communicator and mentor with high credibility among pilots. This person must be organized, visible, extroverted, and comfortable leading from the front while balancing operational standards with a practical understanding of line flying. 

• Provide company-wide leadership and oversight for flight crew operations across all bases
• Directly supervise Base Chief Pilots and support the consistent execution of company standards across the system
• Lead pilot standardization initiatives and promote consistent application of SOPs, policies, and operational expectations
• Participate in pilot recruitment, interviewing, selection, onboarding, retention, and development
• Support pilot accountability through performance management, coaching, and disciplinary processes as needed
• Serve in check pilot functions and conduct or oversee required training and checking events in accordance with company authorization and regulatory requirements
• Work closely with the Director of Operations on operational policy, pilot-related procedures, and flight operations initiatives
• Assist with FAA interactions related to pilot qualifications, standards, manuals, and operational oversight
• Support manual, SOP, and checklist development and revision
• Promote a culture of professionalism, mentorship, accountability, and pilot engagement
• Maintain close coordination with training, scheduling, dispatch, and base leadership to support operational continuity
• Serve as a pilot in the CJ4 on a recurring basis, with an expected flying cadence of approximately one week every other week
• Travel to other company bases as needed, approximately 20% of the time 

• Minimum 5,000 hours total time
• Minimum 3,000 hours multi-engine
• Minimum 2,000 hours turbofan
• Minimum 1,500 hours turbojet PIC
• ATP certificate with AMEL privileges
• Current First Class Medical Certificate
• Previous experience in Part 135 and/or Part 121 operations
• Previous leadership experience in a flight department or air carrier environment
• Strong working knowledge of FAA regulations, air carrier pilot qualification requirements, and operational standards
• Valid driver’s license
• FCC Restricted Radiotelephone Operator Permit 

• CE-525 type rating
• Previous Chief Pilot, Assistant Chief Pilot, Base Chief Pilot, or similar flight operations leadership experience
• Previous check pilot experience
• Previous Part 135 experience
• Experience leading pilot standardization across a multi-base operation
• Experience working directly with the FAA in an operational leadership role
• International operational experience
• Strong reputation for mentorship, professionalism, and pilot credibility

• 401(K) with Company Matching
• Health, Dental, and Vision Insurance
• Short-term Disability
• Long-term Disability
• Group Term Life Insurance
• HSA
• 3 weeks PTO
• Holidays off

Milwaukee, WI

• Part 135 and co-ownership program
• 7/7 schedules with built-in flexibility
• Not on call 24/7
• The majority of our trips return to base the same day
• No airline travel to where your trip begins

• ATP Pilot Certificate AMEL
• Current 1st Class Medical Certificate
• 3,500 Total Time
• 1,500 Turbine PIC
• Valid Driver’s License Valid US Passport with no restrictions FCC Operator Permit
• Able to travel unrestricted to Canada, Mexico, and all countries in the Caribbean
• No incidents, accidents, or FAA sanctions within the last five years
• Ability to lift 50-75 LBS

• CE-525 PIC type rating
• 250 hours in type
• 2,500 hours multi-engine
• Proficient in ProLine 21 Avionics Suite
• Part 121 or part 135 Experience

• 401(k) with company matching
• Health, Dental, and Vision Insurance
• HSA
• Loss of Medical Insurance, short and long-term disability
• Life Insurance
• Paid Meals
• Paid Vacation
• 11% profit-sharing contribution to employee 401(k)

• From $135,000 per year 

To meet the bonus criteria applicants must first be approved by insurance to act as PIC after completion of Jet OUT Captain OE (25 hours), already hold a PIC CE-525 type rating, and successfully complete initial training.

Scottsdale, AZ (SDL) - Non-Commutable

• Part 135 and Co-Ownership program
• 7/7 schedules with built-in flexibility
• Not on call 24/7
• The majority of our trips return to base the same day
• No airline travel to where your trip begins

• 401(k) with company matching
• Health, Dental, and Vision Insurance
• HSA
• Loss of Medical Insurance, short and long-term disability
• Life Insurance
• Paid Meals
• Paid Vacation
• 11% profit sharing contribution to employees 401(k)

• ATP Pilot Certificate AMEL
• Current 1st Class Medical Certificate
• 3,500 TT
• 1,500 Turbine PIC
• Valid Driver’s License
• Valid US Passport with no restrictions
• FCC Operator Permit
• Able to travel unrestricted to Canada, Mexico, and all countries in the Caribbean.
• No incidents, accidents, or FAA sanctions within the last five years
• Ability to lift 50-75 lbs.

• CE-525 PIC type rating
• 250 hours in type
• 2,500 hours multi-engine
• Proficient in ProLine21 Avionics Suite
• Part 121 or part 135 Experience

• To meet the bonus criteria applicants must first be approved by insurance to act as PIC after completion of Jet OUT Captain OE (25 hours), already hold a PIC CE-525 type rating, and successfully complete initial training.

Dallas, TX - Non-Commutable

• Part 135 and Co-Ownership program
• 7/7 schedules with built-in flexibility
• Not on call 24/7
• The majority of our trips return to base the same day
• No airline travel to where your trip begins

• 401(k) with company matching
• Health, Dental, and Vision Insurance
• HSA
• Loss of Medical Insurance, short and long-term disability
• Life Insurance
• Paid Meals
• Paid Vacation
• 11% profit sharing contribution to employees 401(k)

• ATP Pilot Certificate AMEL
• Current 1st Class Medical Certificate
• 3,500 TT
• 1,500 Turbine PIC
• Valid Driver’s License
• Valid US Passport with no restrictions
• FCC Operator Permit
• Able to travel unrestricted to Canada, Mexico, and all countries in the Caribbean.
• No incidents, accidents, or FAA sanctions within the last five years
• Ability to lift 50-75 lbs.

• CE-525 PIC type rating
• 250 hours in type
• 2,500 hours multi-engine
• Proficient in ProLine21 Avionics Suite
• Part 121 or part 135 Experience

• To meet the bonus criteria applicants must first be approved by insurance to act as PIC after completion of Jet OUT Captain OE (25 hours), already hold a PIC CE-525 type rating, and successfully complete initial training.

Fort Lauderdale, FL

• Part 135 and Co-Ownership program
• 7/7 schedules with built-in flexibility
• Not on call 24/7
• The majority of our trips return to base the same day
• No airline travel to where your trip begins

• ATP Pilot Certificate AMEL
• Current 1st Class Medical Certificate
• 3,500 Total Time
• 1,500 Turbine PIC
• Valid Driver’s License Valid US Passport with no restrictions FCC Operator Permit
• Able to travel unrestricted to Canada, Mexico, and all countries in the Caribbean
• No incidents, accidents, or FAA sanctions within the last five years
• Ability to lift 50-75 LBS

• CE-525 PIC type rating
• 250 hours in type
• 2,500 hours multi-engine
• Proficient in ProLine 21 Avionics Suite
• Part 121 or part 135 Experience

• 401(k) with company matching
• Health, Dental, and Vision Insurance
• HSA
• Loss of Medical Insurance, short and long-term disability
• Life Insurance
• Paid Meals
• Paid Vacation
• 11% profit-sharing contribution to employee 401(k)

• From $135,000 per year 

To meet the bonus criteria applicants must first be approved by insurance to act as PIC after completion of Jet OUT Captain OE (25 hours), already hold a PIC CE-525 type rating, and successfully complete initial training.

Dallas/Fort Worth, TX

Jet OUT is looking for a Base Chief Pilot to help support and maintain a high level of professionalism and safety within our flight department. The Base Chief Pilot will be the direct supervisor and primary point of contact for all pilots assigned to the base. Your primary role will be to support the pilots and other flight department personnel and facilitate positive communication channels between the base employees and the Jet OUT main office.

As Jet OUT’s Base Chief Pilot, you are to be highly knowledgeable on Jet OUT’s General Operations Manual, General Training Manual, Operations Specifications, and all other manuals used by the company, as well as the Federal Aviation Regulations and the AFM for aircraft kept at the base.

Your regular duties will include participating in interviews, hiring, onboarding, training, and mentoring new employees as well as performing recurrent training, checking events, and regular performance reviews for base pilots. You will also be responsible for handling interpersonal, performance, or disciplinary issues, coordinating local pilot schedules and training, implementing new and updated procedures, and other tasks necessary for the growth of Jet OUT.

Some travel to Milwaukee, WI and other current and future Jet OUT bases will be necessary, as well as other locations for training purposes and to support Jet OUT flight operations.

As a member of Jet OUT’s management, you will have other responsibilities outside of the flight department, specifically representing Jet OUT in dealings with the local FBO and any other service providers we use. You will also be responsible for safety and security roles and facilitating local drug tests. Additional tasks may be assigned by the CEO, COO, Director of Operations, or Chief Pilot as necessary for the growth of Jet OUT.

The Base Chief Pilot plays a vital role in maintaining the highest standards of safety and operational efficiency, contributing to the overall success of Jet OUT.

• Reports to the Chief Pilot.
• Maintains a close liaison with the Chief Pilot and Director of Operations about department operations.
• Maintains proficiency as a Pilot-in-Command on the CJ4.
• Participates in interviews, hiring, onboarding, and separation processes.
• Supervises local flight crew personnel.
• Mentor new hires.
• Coordinate with the Training Manager regarding the training of flight crews.
• Conducts or supervises training activities of flight crews.
• Conducts 135.293a and 135.299 checking events.
• Conducts regular performance evaluations.
• Manages local pilot flight schedules.
• Coordinates commuter pilot schedule.
• Handles local pilot performance, interpersonal, or disciplinary issues.
• Submits all reports regarding flight crew personnel to the Chief Pilot.
• Coordinates communication between local base and Jet OUT’s main offices.
• Ensures that all aircraft are properly equipped for applicable operations.
• Participates in regularly scheduled. meetings with Chief Pilot and/or Director of Operations.
• Assists Jet OUT in formulating operations policies, coordinates those policies, and coordinates operations and training.
• Assists with manual, SOP, and checklists updates.
• Responsible for crew flight and duty records and crew duties as required by operational and safety standards set forth by Jet OUT and the Federal Aviation Administration.
• Supervises distribution and posting of all information or memoranda relative to any changes affecting company policy, route information, navaids, NOTAMS, requesting of flying aids, aeronautical charts, etc.
• Ensures that all flight crew personnel are certified and supervised according to the requirements specified in the Federal Aviation Regulations.

• Minimum two years’ experience in Part 135 or Part 121 operations
• Minimum one year of experience as PIC in turbojet operations
• ATP Pilot Certificate AMEL
• Current 1st Class Medical Certificate
• 3,500 Hours Total Time
• 1,500 Hours Multi-Engine
• 500 Hours Turbofan
• Valid Driver’s License
• FCC Restricted Radiotelephone Operator’s Permit
• Must be located within one hour of FTW

• One year experience as PIC in Part 135 or Part 121 operation
• 4,000 Hours Total Time
• CE-525 Type Rating
• 100 Hours of CE-525C
• Bachelor’s degree
• Aviation Management Experience
• International Experience

• 401K with Company Matching
• Health, Dental, and Vision Insurance
• Short Term Disability
• Long Term Disability
• Group Term Life Insurance
• HSA
• 3 weeks PTO
• Holidays off

• $150,000 with regular raises for years of service

To meet the bonus criteria applicants must first be approved by insurance to act as PIC after completion of Jet OUT Captain OE (25 hours), already hold a PIC CE-525 type rating, and successfully complete initial training.