The Assistant Chief Pilot supports the Chief Pilot in managing daily flight operations, ensuring regulatory compliance, safety, and alignment with [Company]’s mission. Acting as a liaison between crews and leadership, the role promotes a strong safety culture and continuous improvement. This role supervises pilots, assists with training and evaluations, and addresses crew concerns, escalating issues as needed. At times, they perform line pilot duties, provide administrative coverage, and support the training department through instruction and evaluation. The Assistant Chief Pilot embodies and lives out [Company]’s mission and values.
This hybrid position is based at a [Company] base and from home, with travel to other [Company] bases as needed. Must live in either Minnesota or Wisconsin near a [Company] base.
Key Responsibilities:
Flight Operations & Regulatory Compliance:
Supports daily flight operations aligned with patient care, regulations, and SOPs
Monitors operational issues and coordinates with the Chief Pilot for resolution
Holds delegated FAA Tier 1 operational control under 14 CFR Part 135.77
Acts on behalf of the Chief Pilot when delegated; supervises pilots and ensures compliance with FARs, GOM, and training standards
Maintains check pilot certification and supports pilot evaluations and training records
Ensures accurate flight documentation and participates in compliance audits and monthly aviation meetings
Leadership & Talent Development:
Engages and mentors pilots, fostering a culture aligned with [Company]’s mission
Supports recruitment, retention, performance, and disciplinary documentation in collaboration with HR
Oversees scheduling, pilot orientation, and internal programs to support operational readiness
Collaboration & Communication:
Maintains a positive attitude, with open, honest, and respectful communication to all stakeholders
Provides on-time feedback that contributes to ongoing development of pilots
Work in collaboration with leaders from other departments to ensure the bases operate in a manner that supports [Company]’s patients, partners, and values
Quality, Safety & Risk Management:
Actively participates in [Company]’s Safety Management System (SMS) including reporting hazards and incidents encountered in daily operations
Understands, complies, and promotes the [Company] Safety Policy; and other safety duties as assigned by the Director of Aviation Safety, including:
Aviation Safety Representative
Assisting in the investigative process for Incident Reports
Assisting in the Base Safety program
Minimum Requirements:
1–3 years of strong leadership experience
Commercial pilot certificate and instrument Rating for category and class of aircraft (ATP in category meets this requirement)
2000 hours total flight time
1500 hours flight hours in category
1000 hours PIC in category
500 hours of rotorcraft turbine time
200 hours of cross
100 hours of unaided night - 50 hours of unaided night can be accepted with a minimum of 100 hours of aided night
50 hours of hood or actual time instrument time in flight in category (Simulator time does not count) A pilot that is dual qualified in fixed wing with 100 hours of actual instrument time can reduce this requirement to 25 hours
Proficient in Microsoft Office; able to travel and work flexible hours
Holds a valid driver’s license and FAA First or Second-Class Medical Certificate
Maintains currency in at least one [Company] aircraft; knowledgeable in 14 CFR Parts 91, 119, and 135
Possesses a Commercial Pilot Certificate with Instrument Rating (ATP acceptable)
Strong interpersonal, motivational, and team-building skills
Proven ability to foster an inclusive, collaborative, and ethical work environment
Skilled in conflict resolution, relationship building, and operational problem-solving
Customer-focused with effective communication and active listening abilities
Preferred Qualifications:
Bachelor’s degree in a related field
Certified Flight Instructor Instrument and Instructor Pilot Experience
Experience in coaching, mentoring, and developing a team
What We Offer:
Compensation: annual salary of $140,000 – $158,000 depending on experience
Additional $775 bonus for each front-line pilot shift picked up
Insurance starting the first of the month after date of hire:
Medical, Dental and Vision Insurance
Health Savings (HSA) on qualified plans plus an employer match
Employer Matching on 401(k)
Competitive Paid Time Off to foster a work/life balance
Life and AD&D, Short- and Long-Term Disability, Critical Illness and Accident Insurance
Cell Phone and Internet Stipends available
Annual $1500 reimbursement available for professional development
Compliance/HIPAA: Must perform work in the manner prescribed by documented work process in order to ensure compliance with all rules and regulations, accreditation standards and laws that apply, specifically work processes that involve billing practices, for avoiding activities that constitute fraud and abuses
Employment Status Requirements: [Company] does not sponsor employment visas of any kind. As a pre-condition of employment, all applicants must be authorized to work in the United States.
[Company] is committed to creating an inclusive workplace where all individuals are treated with respect and dignity. We are an Equal Employment Opportunity (EEO) employer and believe in providing equal employment opportunities to all employees and applicants without regard to race, color, religion, sex, sexual orientation, gender identity or expression, pregnancy, age, national origin, disability status, genetic information, veteran status, marital or family status, status with regard to public assistance, or any other characteristic protected by federal, state, or local laws.
Our commitment to an equitable workplace extends to all aspects of employment, including recruitment, hiring, promotions, transfers, training, working conditions, compensation, benefits, and termination. We are dedicated to maintaining a workplace that is free of discrimination, harassment, and retaliation, and where all individuals can thrive professionally.
If you require any accommodations to apply or participate in our hiring process, please contact [Company] human resources.