Assistant Chief Pilot

About the role

Wing is looking for an Assistant Chief Pilot to join the Flight Operations team in Dallas, Texas. Reporting directly to the Chief Pilot, you will inspire, lead, and empower 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. The position is subject to Wing’s Drug and Alcohol testing policy and FAA/DOT regulatory requirements.

Responsibilities

• 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.
• 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%) as required, sometimes for extended periods.

Requirements

• 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 in aviation, transportation, or other safety‑critical operations.
• 3+ years of experience as a PIC in Part 135 commercial drone delivery operations or equivalent, with a passion for aviation and industry development.
• 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 a clean driving record within the last 36 months.
• Valid FAA Third Class Medical Certificate (or higher) issued within the previous 36 months.
• Extensive knowledge and experience working within an aviation regulatory framework.
• 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 maintaining rigorous attention to detail.
• Ability to maintain attention to detail for extended periods in a monitoring role.
• Willingness to meet Pilot Records Database (PRD) consent requirements.
• Subject to Wing’s Drug and Alcohol testing policy; pre‑employment drug testing required; prior positive test disqualifies.

Pay

Salary range $140,000 — $148,000 USD, plus bonus, equity, and benefits.

Schedule

Rotating 7‑day schedule within crew duty time limits, including weekends and holidays; up to 20% travel within the United States.