Direct entry Captain Type rated Learjet

Company Description

HIGHTAIL Air Charter, LLC is a United States–based air charter company headquartered in Wheeling, Illinois. The organization focuses on safe, reliable, and responsive private air transportation services for a variety of clients. Team members work in a professional environment that values sound judgment, operational excellence, and customer service. The company offers opportunities to operate well‑maintained aircraft while working closely with a small, dedicated team.

HIGHTAIL Air Charter is committed to regulatory compliance, safety, and continuous improvement in its flight operations.

This full‑time, on‑site Direct Entry Captain position is based in Pinedale, WY and requires a type rating on the Learjet 35A/31/55. The Captain is responsible for the safe and efficient conduct of all phases of flight operations, including pre‑flight planning, fuel calculations, performance planning, weather evaluation, and post‑flight documentation. Daily duties include conducting thorough pre‑flight and post‑flight inspections, monitoring aircraft systems, coordinating with dispatch and ground personnel, and ensuring compliance with all applicable FAA regulations and company procedures.

The Captain will brief passengers, provide a professional and courteous onboard experience, and maintain high standards of crew resource management and cockpit discipline. The role also involves maintaining currency and proficiency through training, adhering to safety management practices, and supporting operational readiness, including occasional irregular schedules, weekends, and holidays as required.

• Current and valid FAA Airline Transport Pilot (ATP) certificate with a Learjet 35A/31/55 type rating and current First Class Medical certificate.
• Minimum flight time consistent with company and regulatory requirements for Captain, including substantial multi‑engine turbine and jet experience.
• Demonstrated proficiency in IFR operations, high‑performance and high‑altitude flying, and operating into and out of diverse airports and weather conditions.
• Strong understanding of FAA regulations, company operating procedures, and safety management systems, with a proven record of regulatory compliance.
• Excellent decision‑making, situational awareness, and crew resource management skills, with the ability to manage workload and prioritize safety under time pressure.
• Professional communication and interpersonal skills, including the ability to interact effectively with passengers, crew members, dispatch, and maintenance teams.
• Ability to work an on‑site, full‑time schedule in Pinedale, WY, including variable hours, overnights, weekends, and holidays as operationally needed.
• Proficiency with modern avionics, flight planning software, and electronic flight bag (EFB) systems; comfortable with technology and digital documentation.
• High standard of professionalism, reliability, and integrity, with a focus on customer service and representing the company positively at all times.