Wings Air Helicopters is seeking a Chief Pilot to lead our flight operations department. The Chief Pilot will oversee pilot training, standardization, and compliance, ensuring all operations meet FAA and company standards. This position requires a strong background in rotorcraft operations under 14 CFR Parts 91 and 135, as well as proven leadership and communication skills. Wings Air conducts a large variety of missions that include tours, charters, HAA organ/blood/tissue transfers, aerial photography/cinematography, flight instruction, powerline patrol, and wildlife surveys. Currently we operate a fleet that consists of AS350s, an AS355N, and an R44 II out of Westchester County Airport (KHPN). We are currently expanding operations and will have an auxiliary base out of Pompano Beach, FL (KPMP). The chief pilot will be expected to occasionally travel to Florida.

Primary Responsibilities

• Manage and supervise company flight operations under Parts 91 and 135
• Ensure compliance with FAA regulations, company manuals, and Operations Specifications
• Oversee pilot hiring, training, qualification, and recurrent programs
• Conduct and coordinate pilot proficiency checks and flight evaluations
• Maintain pilot records, currency, and qualification documentation
• Serve as primary liaison with the FSDO and company POI
• Promote and maintain a strong safety culture through participation in the company SMS
• Collaborate with the Director of Operations and Director of Maintenance to ensure efficient, safe, and compliant operations
• Perform flight duties as needed to support operational requirements

Job Requirements:

• Part 119.71(d) requirements must be met or will be met by January 2026
• Commercial Rotorcraft License
• Instrument Rating
• CFI Rating
• R44 SFAR Endorsement
• Strong communication skills and attention to detail
• U.S. citizen, or have legal authorization to work in the United States

Preferred:

• Prior Chief Pilot/Management experience
• ATP Rotorcraft
• Prior experience as a Training Captain or Check Pilot in a Part 135 organization
• Strong knowledge of greater NYC area airspace
• AS350/AS355 experience
• Proficient with Microsoft Word & Excel, Adobe Acrobat, and Google Suite
• Familiarity with ARGUS and WYVERN