The Chief Pilot provides leadership, regulatory oversight, and day-to-day management of its Part 135 flight operations. The Chief Pilot is a required management position under 14 CFR Part 119, reports directly to the Director of Operations, and works closely with the Director of Operations, Director of Maintenance, Training Department, Safety Manager, Cargo Manager and Department, and FAA Certificate Management Team. The Chief Pilot must be experienced Part 135 aviation and has strong leadership skills, sound operational judgment, extensive knowledge of FAA regulations, Operations Specifications, training and checking requirements, recordkeeping management, and safety management principles.

About [redacted], LLC

What We Do at [redacted]

At [redacted], we deliver fast, flexible, and reliable air charter services across Hawaii and beyond. Our mission is to move what matters—safely, efficiently, and with a personal touch.

Why Join Us?

We’re more than just an air carrier—we’re a tight-knit team with a passion for aviation, precision, and service. What sets us apart? Our commitment to safety, our can-do spirit, and the trust we’ve built with clients who count on us to deliver—every time.

Ready to take flight with a company that values your skills and fuels your growth? [redacted] is where your aviation career takes off.

Description

Job Responsibilities

1. Flight Operations Management

• Exercise operational control as authorized and assigned by [redacted] and ensure flights are conducted safely in accordance with applicable regulations, Operations Specifications, [redacted] manuals, policies, and procedures.

• Provide leadership and day-to-day oversight of [redacted] pilots and flight operations.

• Maintain qualification as Pilot in Command in at least one type of aircraft operated by [redacted].

• Schedule flight crews for duty and ensure crew assignments comply with applicable qualification, currency, flight time, duty time, rest, and operational requirements.

• Manage pilot payroll, including review and verification of pilot schedules, duty assignments, applicable pay items, and payroll information.

• Coordinate closely with Operations Control, Maintenance, the Cargo Manager and cargo personnel, Safety, Training, and [redacted] leadership to support safe and efficient operations.

• Exercise the authority and perform the duties assigned to the Chief Pilot by [redacted]'s manuals, Operations Specifications, and applicable regulations.

2. Crew Resource Management

• Ensure flight crewmembers remain properly trained, qualified, current, and authorized for assigned duties.

• Maintain pilot standardization and ensure compliance with [redacted] manuals, policies, procedures, Operations Specifications, and applicable federal aviation regulations.

• Oversee pilot training, checking, proficiency, and qualification programs in coordination with the Training Manager and Director of Operations.

• Administer [redacted]'s Second-in-Command Professional Development Program (SIC PDP) in accordance with applicable regulations, FAA requirements, Operations Specifications, and company procedures.

• Revise the General Training Manual (GTM) as needed to maintain an effective, current, and compliant training program.

• Participate in pilot recruiting, interviewing, selection, onboarding, evaluation, and development.

• Conduct periodic performance reviews of pilots to assess professional standards, operational performance, regulatory compliance, standardization, and adherence to company policies and procedures.

3. Regulatory Compliance Management

• Maintain effective working relationships with the FAA and other regulatory agencies.

• Participate in FAA SAS activities, surveillance, inspections, audits, and certification or authorization projects.

• Ensure flight operations records are properly maintained, including pilot training, qualification, checking, currency, duty and flight time records, and other records required by applicable regulations, Operations Specifications, and company manuals.

• Ensure appropriate pilot records and qualification information are maintained, including compliance with Pilot Records Database (PRD) requirements.

• Maintain all flight operations manuals, publications, and controlled documents at their current revisions and ensure they are published electronically within [redacted]'s flight operations management software.

• Assist with revisions to company manuals, training programs, Operations Specifications, and operational policies and procedures.

• Administer [redacted]'s TSA 12.5 security program and ensure applicable flight operations personnel and activities comply with program requirements.

• Coordinate and communicate with the Hawaii Department of Transportation (HDOT) and airport operations management regarding airport planning, projects, construction activities, operational impacts, and compliance matters affecting [redacted] operations.

4. Safety Management

• Support [redacted]'s Safety Management System (SMS) and promote a positive, professional safety reporting culture.

• Participate in safety investigations, risk assessments, corrective actions, safety promotion, and Root Cause Analysis (RCA) investigations as directed by the Director of Operations.

• Support and participate in the implementation and administration of ASAP, LOSA, FOQA, and other applicable safety assurance programs.

• Coordinate with internal departments and company leadership to address operational risks and support continuous safety improvement.

Perform other duties as assigned by the Director of Operations or [redacted] leadership.

Required Qualifications 

The Chief Pilot must meet all applicable qualification requirements of 14 CFR § 119.71 for the operations conducted by [redacted], including the applicable pilot certificate, ratings, and required experience. 

• Hold the pilot certificates and ratings required by 14 CFR § 119.69 and 119.71 for the Chief Pilot position and the type of Part 135 operations conducted by [redacted]. 

• Meet the applicable recent pilot-in-command experience requirements prescribed by 14 CFR § 119.71. 

• Be qualified to serve as Pilot in Command in [redacted]'s operations, as applicable. 

• Possess a strong working knowledge of the 14 CFR Parts as applicable to [redacted] operations. 

• Have previous experience as a Training Captain in Part 135 or comparable commercial aviation operations. 

• Be proficient in Microsoft Office applications and the use of an iPad in an aviation operational environment. 

• Possess demonstrated leadership, communication, decision-making, organizational, and personnel management skills. 

• Be able to effectively interact with FAA inspectors, [redacted] leadership, pilots, maintenance personnel, the Cargo Manager and cargo personnel, customers, airport authorities, and other stakeholders. 

Appointment to the position is subject to satisfaction of all applicable regulatory requirements and FAA acceptance as required by 14 CFR Part 119.

Preferred Experience 

• Five or more years of recent experience as a Part 135 Chief Pilot. 

• Strong working knowledge of applicable federal aviation regulations and FAA Operations Specifications (OpSpecs). 

• Extensive experience working directly with FAA inspectors and Certificate Management Teams. 

• Familiarity with and user proficiency in the FAA Safety Assurance System (SAS) Portal. 

• User proficiency with WebOPSS, including the development, revision, and management of Operations Specifications. 

• Experience with the FAA Pilot Records Database (PRD). 

• Experience with TSA 12.5 security programs and applicable air cargo security requirements. 

• Highly knowledgeable regarding FAA required Drug and Alcohol (D&A) testing programs, including applicable regulatory and administrative requirements. 

• Experience with a Hazardous Materials Will-Carry program, including associated training, manual, and operational requirements. 

• Significant experience implementing and administering an FAA-compliant Safety Management System (SMS). 

• Experience with Aviation Safety Action Programs (ASAP). 

• Experience conducting or administering Line Operations Safety Audits (LOSA). 

• Experience with Flight Operational Quality Assurance (FOQA) or comparable flight data monitoring programs. 

• Previous experience as an FAA authorized Check Pilot.

• Experience developing, revising, and administering Part 135 manuals, training programs, policies, and procedures. 

• Experience managing pilot standardization, line checks, proficiency checks, recurrent training, and regulatory recordkeeping systems. 

• Operational experience with single and multi-engine turboprop airplanes in cargo operations. 

• Experience using aviation and workforce management software applications, including JetInsight, Fleet Manager, When I Work, and ForeFlight, or comparable systems. 

Job Type: Full-time

Base pay is $150,000 plus additional salary based on knowledge and experience.

Benefits:

• Health insurance

• Dental insurance

• Vision insurance

• Pharmacy Insurance

• 401(k) with company matching

Work Location: In person

[redacted] is committed to hiring a diverse workforce and sustaining and inclusive culture providing equal opportunities to associates and applicants for employment without regard to race, color, religion, gender, national origin, marital status, genetic information, age, disability, sexual orientation, gender identity or status as a Vietnam-era or special disabled veteran in accordance with applicable federal laws In addition, [redacted] complies with applicable state and local laws governing nondiscrimination in employment in every location where [redacted] has facilities. This policy applies to all terms and conditions of employment, including but not limited to hiring, placement, promotion, termination, layoff, recall, transfer, leave of absence, compensation and training. 

Salary

$140,000 - $165,000 per year