Jet OUT is a growing Part 135 air carrier operating a Citation CJ4 fleet in a dynamic domestic and international environment. We are committed to professional standards, operational discipline, and a pilot-focused culture that values safety, accountability, consistency, and service. This role is designed for a leader who can help maintain high standards across the operation while building credibility and trust with line pilots, Base Chief Pilots, and flight department leadership.

Position Summary

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.

Key Responsibilities

• 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

Position Details

• Full-time leadership position

• Monday through Friday core schedule

• On-call availability required

• Minimal weekend availability expected when operationally necessary

• Approximately 20% travel to other bases and company locations

• Milwaukee area residency required, within one hour drive time

• Relocation benefits available

Required Qualifications

• 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

Preferred Qualifications

• 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

Ideal Candidate Profile

The successful candidate will be:

• Pilot-friendly and approachable

• Highly credible with line pilots and base leadership

• A strong mentor and coach

• Organized and dependable

• Comfortable holding standards while maintaining trust and respect

• Extroverted, visible, and effective in cross-functional communication

• Committed to building consistency and accountability across the operation

Benefits Benefits Include:

• 401(k) with company match

• Health, dental, and vision insurance

• Short-term disability

• Long-term disability

• Group term life insurance

• HSA

• 3 weeks PTO

• Holidays off

How to Apply

Please submit your cover letter and resume to Anne Pavlik

Pay: From $180,000.00 per year