Chief Pilot Jobs in Wisconsin (NOW HIRING)

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.

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, WI 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, 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 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, 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

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

Ideal Candidate Profile

The successful candidate will be:

• Pilot-friendly and approachable

• Highly credible with line pilots

• A strong mentor and coach

• Organized, dependable, and detail-oriented

• Comfortable holding standards while maintaining trust and respect

• Visible and engaged with the pilot group

• Calm, professional, and constructive when resolving issues

• Committed to consistency, accountability, and operational discipline

• Able to balance line pilot perspective with leadership responsibility

• Focused on supporting a strong base culture and the continued growth of Jet OUT

Compensation and Benefits

Jet OUT offers a competitive compensation and benefits package for this leadership position.

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