Milwaukee Base Chief Pilot — Lead, Mentor & Standards

Jet OUT; Milwaukee (WI); On-site; USD 150,000 - 210,000; Full time

Job summary

Jet OUT is seeking a Base Chief Pilot for the Milwaukee, WI base to provide day-to-day leadership, mentorship, and operational oversight for pilots assigned to the Milwaukee base, ensuring adherence to Jet OUT procedures and safety standards.

This role combines on-the-ground leadership with line flying; you will mentor crews, support training, manage schedules, and coordinate with the System Chief Pilot and Training Manager to maintain a strong, pilot-focused culture across the base.

Qualifications

• Minimum two years of experience in Part 135 and/or Part 121 operations.
• Minimum one year of experience as PIC in turbojet operations.
• ATP certificate with AMEL privileges.
• Minimum 3,500 hours total time.
• Minimum 1,500 hours multi-engine time.
• Minimum 500 hours turbofan time.
• FCC Restricted Radiotelephone Operator Permit.
• Must reside within one hour of Milwaukee, WI area.
• Strong working knowledge of FAA regulations, company manuals, flight operations standards, and professional pilot expectations.
• Demonstrated ability to lead, mentor, and communicate effectively with pilots.

Responsibilities

• Serve as the direct supervisor and primary point of contact for pilots assigned to the Milwaukee, WI base.
• Report to the System Chief Pilot and maintain close communication regarding base operations, pilot performance, staffing, scheduling, and operational needs.
• Maintain proficiency and currency as CJ4 Pilot-in-Command and lead by example as a professional line pilot and base-level flight department leader.
• Support pilot standardization and the consistent execution of Jet OUT policies, SOPs, checklists, manuals, and operational expectations.
• Serve as the assigned on-call Base Chief Pilot when scheduled, providing timely leadership support for pilot, operational, safety, crew readiness, and base-level issues requiring Chief Pilot involvement outside normal business hours.
• Mentor new hires, support pilot development, and participate in pilot interviews, selection, onboarding, and retention efforts as requested.
• Assist with recurrent training, local training coordination, pilot readiness, and required checking events, including 135.293 and 135.299 events, when authorized and qualified.
• Coordinate with the System Chief Pilot, Training Manager, Scheduling, Dispatch, and other operational leaders to support flight crew readiness and base performance.
• Conduct regular pilot performance reviews and provide coaching, feedback, and development support.
• Address pilot performance, interpersonal, or disciplinary matters at the base level, escalating when appropriate.
• Manage and coordinate local pilot schedules in alignment with company operational needs.
• Support base-level communication, implementation of updated procedures and policies, safety and security initiatives, local service provider relationships, and other duties assigned in support of Jet OUT’s growth, safety, and operational performance.
• Milwaukee, Wisconsin-based role
• Reports to the System Chief Pilot
• Monday through Friday core schedule
• Combination of office leadership responsibilities and line flying
• Occasional evening, weekend, and on-call availability required based on operational needs , including assigned on-call Base Chief Pilot coverage
• Some travel to other Jet OUT locations may be required
• Must reside within one hour of the Milwaukee area

Skills

Leadership

Mentorship

Communication

FAA regulations knowledge

Pilot-in-Command leadership

Staff supervision

Education

ATP certificate with AMEL privileges

Job description

Jet OUT is seeking a Base Chief Pilot for the Milwaukee, WI base to provide day-to-day leadership, mentorship, and operational oversight for pilots assigned to the Milwaukee base, ensuring adherence to Jet OUT procedures and safety standards.

This role combines on-the-ground leadership with line flying; you will mentor crews, support training, manage schedules, and coordinate with the System Chief Pilot and Training Manager to maintain a strong, pilot-focused culture across the base.