Base Chief Pilot - Milwaukee, WI

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Milwaukee (WI)

On-site

USD 120,000 - 180,000

Full time

4 days ago

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Benefits offered by this job

401(k) match

Health insurance

Short-term disability

Long-term disability

Life insurance

Health Savings Account

PTO 3 weeks

Holidays off

Job summary

Jet OUT in Milwaukee, WI seeks a Base Chief Pilot to lead pilots at the Milwaukee base. You will report to the System Chief Pilot and ensure consistent execution of Jet OUT procedures, training support, and pilot development.

The role blends leadership with line flying, requires strong communication, and demands a visible, mentor-focused approach to maintain safety and operational discipline 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 required.
Current First Class Medical Certificate required.
Minimum 3,500 hours total time.
Minimum 1,500 hours multi-engine time.
Minimum 500 hours turbofan time.
Must reside within one hour of Milwaukee area or relocate.
FCC Radiotelephone Permit required.

Responsibilities

Supervise pilots assigned to the Milwaukee base and serve as primary contact.
Report to System Chief Pilot and maintain base communications on operations and staffing.
Maintain CJ4 PIC proficiency and lead by example as a line pilot and base leader.
Support standardization and adherence to Jet OUT procedures and policies.
Mentor new hires and participate in pilot development and interviews as needed.
Coordinate with Training Manager and other leaders to ensure readiness.
Conduct regular performance reviews and provide coaching to pilots.
Address performance or disciplinary matters at base level and escalate when needed.

Skills

Leadership

Mentoring

Communication

Education

ATP certificate with AMEL privileges

First Class Medical Certificate

FCC Restricted Radiotelephone Operator Permit

Tools

CE-525 type rating

CJ4 operating experience

Job description

About Jet OUT

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.

Base Chief Pilot, Full-Time

Location: Milwaukee, Wisconsin

About Jet OUT

As we continue to grow, our base leadership team plays a critical role in maintaining the standards, communication, and professionalism that define our operation. The Base Chief Pilot is one of the most visible leaders in the pilot group and serves as the primary connection between assigned flight crews, base operations, and company flight department leadership.

Position Summary

Jet OUT is seeking a Base Chief Pilot for our Milwaukee, Wisconsin base. Reporting to the System Chief Pilot, the Base Chief Pilot provides day-to-day leadership, mentorship, and operational oversight for pilots assigned to the Milwaukee base.

This is a flying leadership role designed for a pilot who is respected on the line, comfortable holding standards, and committed to supporting a professional, accountable, and pilot-focused culture. The Base Chief Pilot will help ensure consistent execution of Jet OUT procedures, support training and checking activities, assist with pilot development, and serve as a trusted resource for both pilots and flight department leadership.

This role is intended for a pilot leader who wants more than a title — someone who wants to help build, lead, and protect the standard at one of Jet OUT’s most important bases.

The ideal candidate is approachable, organized, credible, and visible. This person should be comfortable leading by example, communicating directly, resolving issues professionally, and helping build a base culture that reflects Jet OUT’s standards across the system.

Key Responsibilities

Serve as the direct supervisor and primary point of contact for pilots assigned to the Milwaukee 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 a 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.

Position Details

Full-time leadership position
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
Aircraft: Citation CJ4

Required 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
Current First Class Medical Certificate
Minimum 3,500 hours total time
Minimum 1,500 hours multi-engine time
Minimum 500 hours turbofan time
Valid driver’s license
FCC Restricted Radiotelephone Operator Permit
Must reside or be willing to relocate within one hour of the Milwaukee area
Strong working knowledge of FAA regulations, company manuals, f light operations standards, and professional pilot expectations
Demonstrated ability to lead, mentor, and communicate effectively with pilots

Preferred Qualifications

CE-525 type rating
Citation CJ4 operating experience
100 hours or more in CE-525C aircraft
Previous Part 135 PIC experience
Previous check pilot, instructor, training captain, lead pilot, assistant chief pilot, or base leadership experience
International operating experience

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