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Wing (Alphabet) Cover

Assistant Chief Pilot

Wing (Alphabet)
Durham, North Carolina, United States Full Time USD 140,000 - 148,000 p.a. Sep 19, 2026

About the Job

Wing is looking for an Assistant Chief Pilot to join our Flight Operations team. This role is based onsite in Dallas, Texas. As our Assistant Chief Pilot, you will play a pivotal leadership role in shaping the future of autonomous aviation. Reporting directly to the Chief Pilot, you will inspire, lead, and empower o...

Note: This position is subject to Wing’s Drug and Alcohol testing policy in accordance with company procedures and DOT/FAA regulatory requirements. Wing is a Zero Tolerance Drug Free Workplace. All prospective employees in FAA/DOT-regulated roles are subject to pre-employment drug testing. Any applicant applying to ...

Assist the Chief Pilot in overseeing the safe and compliant daily operation of Wing’s delivery business in the United States, including ongoing commercial delivery operations and demonstrations/tests for regulators and other external stakeholders

Key Responsibilities

Wing is looking for an Assistant Chief Pilot to join our Flight Operations team. This role is based onsite  in Dallas, Texas. As our Assistant Chief Pilot, you will play a pivotal leadership role in shaping the future of autonomous aviation. Reporting directly to the Chief Pilot, you will inspire, lead, and empower our Pilot-in-Command (PIC) Managers and sUAS Flight Operators, ensuring operational excellence, mission readiness, and continuous team development across Wing's commercial drone delivery service. If you are an experienced leader with 8+ years of managing-high performing teams in safety-critical environments and are passionate about driving cutting-edge flight operations, we want to hear from you. 
Work closely with the Chief Pilot to manage PIC operational performance, availability, readiness, and scheduling
Work closely with the Chief Pilot to support Policy, Regulatory, Operations, and other teams
Maintain qualification for and function as a Part 135 Pilot-in-Command for Wing’s highly autonomous drone delivery service on a regular basis
Function as a people manager for a team of 3-5 PIC Managers
Enable professional and skill development of the PIC Managers and PICs on your team
Assist the Chief Pilot with ensuring the readiness and availability of PIC Stations and Operations Rooms and associated equipment
Facilitate onboarding of newly hired crew members
Exercise specific delegated operational authority on behalf of the Chief Pilot or Director of Operations, including as a duty Remote Operations Control Center supervisor 
Directly support Wing’s public and government outreach efforts 
Maintain strict confidentiality when dealing with sensitive information
Travel within the United States (up to 20%) required and sometimes for extended periods

Required Skills & Abilities

8+ years of experience with commercial/civil or public UAS operations or university-level education and training in civil UAS operations or military equivalent
5+ years of people management experience with 5+ direct reports or more in aviation, transportation, or other safety-critical operations
3+ years of experience as a PIC in Part 135 commercial drone delivery operations or equivalent, and a passion for aviation and the ongoing development of this new industry. 
Current FAA Part 107 Remote Pilot certificate. If applicable, Part 107 recurrent certificate: only the ALC-677 course is accepted
Current driver’s license and clean driving record within the last 36-months
Must hold a valid FAA Third Class Medical Certificate (or higher) with an issuance date within the previous 36 months 
Extensive knowledge and experience working with an aviation regulatory framework
A determination to recruit and foster the development of diverse teams
Experience with technical or engineering record keeping methods and tools
Experience working with web-based monitoring and control systems
Ability to communicate clearly in spoken and written English
Ability to work a rotating 7-day schedule within crew duty time limits, including weekends and holidays
Willingness to travel to complete initial and recurrent training
Ability to work independently and in teams while still maintaining rigorous attention to detail
Ability to maintain attention to detail for extended periods in a monitoring role  
Willing to meet Pilot Records Database (PRD) consent requirements 
The US base salary range for this full-time position is the salary range below + bonus + equity + benefits. Wing’s salary ranges are determined by role, level, and location. Your recruiter can share more about the specific salary range for your location during the hiring process.
Salary Range
$140,000—$148,000 USD
Wing is an

Qualifications

Experience: 3 years experience

Apply now

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