0025 - Chief Pilot

Alaka'i Services Group Inc / Po'e Hana Group, Inc.

$120K — $150K *
Aerospace & Defense
11 - 15 years of experience
Job Overview by Ladders

Qualifications

  • 11+ years of experience in logistics or aviation operations
  • Comprehensive knowledge of flight operations and safety regulations
  • Proven ability to lead major technical assignments
  • Strong skills in evaluating performance and driving project success
  • Technical expertise across multiple projects or teams
  • Experience in supervising and mentoring personnel

Responsibilities

  • Direct all flight operations to ensure safety and compliance
  • Supervise recruitment and training of pilots
  • Establish standard operating procedures for the flight department
  • Conduct flight proficiency evaluations and check-rides
  • Manage crew scheduling and fatigue risk systems
  • Liaise with civil aviation authorities for regulatory compliance
  • Advise on aircraft procurement and strategic flight planning

Benefits

  • Support for travel to various operational sites
  • Participation in cross-functional collaboration
  • Opportunities for professional development and training
  • Engagement in high-impact assignments in dynamic environments
  • Ability to influence operational effectiveness and project outcomes
Full Job Description
Job Purpose

The purpose of this position is to support mission-critical logistics, sustainment, operational, facilities, training, and mission-enabling activities in support of U.S. Government and Department of Defense objectives throughout the Indo-Pacific region. Personnel in this role contribute to the planning, coordination, execution, and sustainment of complex operations in dynamic and geographically dispersed environments. The position supports operational readiness, resource integration, mission effectiveness, and stakeholder collaboration while ensuring compliance with applicable policies, procedures, and security requirements. Duties are performed in support of contingency, expeditionary, and steady-state operations and may require coordination with Government personnel, mission partners, and cross-functional teams to achieve program objectives.

Position Overview/Functional Role:

This role directs all flight operations to ensure the highest standards of safety and regulatory compliance. Supervises the recruitment, training, and performance evaluation of all pilots within the organization. Establishes standard operating procedures and flight manuals to maintain consistency across the flight department. Conducts regular check-rides and flight proficiency evaluations to certify crew competency. Manages crew scheduling and fatigue risk management systems to optimize operational readiness. Liaises with civil aviation authorities to ensure the organization meets all legal and certification requirements. Advises executive leadership on aircraft procurement, operational budgets, and strategic flight planning. Oversees the safety management system (SMS) to proactively identify and mitigate operational risks. Serves as a technical subject matter expert during incident investigations or emergency response activations.

Job Duties and Responsibilities

The job duties and responsibilities of this position include, but are not limited to, the following:
  • Work at various sites, both CONUS and OCONUS, with travel as required.
  • Perform duties associated with the assigned functional role.
  • Perform additional duties as assigned.


Skill Level Requirements - Senior
  • 11+ years' experience
  • Possesses and applies a comprehensive knowledge across key tasks and high impact assignments.
  • Plans and leads major technical assignments.
  • Evaluates performance results and recommends major changes affecting short-term project growth and success.
  • Functions as a technical expert across multiple project assignments.
  • May supervise others.


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