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Chief Pilot - Part 135 in Rapid City, South Dakota at Riddle s Group Save New Riddle s Group Rapid City, South Dakota, 57703, United States Posted on October 9, 2026 New job! Apply early to increase your chances of getting hired. Explore Related Opportunities Military Enlisted Tactical Operations and Air/Weapons Specialists and Crew Members jobs near me in South Dakota Jobs near me in South Dakota Military Enlisted Tactical Operations and Air/Weapons Specialists and Crew Members jobs Job Description Black Hills Aviation is part of the Riddle's Group, a family-owned company with a diverse portfolio of businesses throughout the region. Our aviation operation is based in Rapid City and is focused on providing safe, professional, and reliable aviation services. We are seeking an experienced Chief Pilot to lead our flight operations and play a key role in the development and management of our FAA Part 135 operation. This is a hands-on leadership position for an experienced aviation professional who understands the regulatory, operational, and safety responsibilities associated with Part 135 operations. Position Summary The Chief Pilot is responsible for the leadership and oversight of the company's flight crew and flight operations. This position ensures that flight operations are conducted safely and in accordance with FAA regulations, company policies, Operations Specifications, and applicable company manuals. The Chief Pilot will oversee pilot qualifications and training, crew scheduling, operational standards, safety, and regulatory compliance while working closely with company leadership and other aviation management personnel. The ideal candidate will have significant Part 135 experience and prior experience serving as a Chief Pilot, along with strong leadership, communication, and operational decision-making skills. This is an on-site role, located in the Rapid City, South Dakota area. Key Responsibilities Serve as the company's designated Chief Pilot for Part 135 operations, subject to FAA approval and qualification. Provide leadership, direction, and oversight to all flight crew members. Ensure flight operations comply with applicable FAA regulations, Operations Specifications, company manuals, and established safety procedures. Oversee pilot qualifications, currency, proficiency, training, and records. Coordinate initial, recurrent, upgrade, and other required pilot training. Maintain accurate pilot qualification and training documentation. Develop and manage pilot schedules while maintaining compliance with applicable crew qualification, duty, and rest requirements. Monitor flight operations and ensure pilots adhere to established company procedures and operational standards. Provide operational guidance regarding weather, routing, aircraft performance, airport considerations, and other flight-related matters. Promote sound aeronautical decision-making and a strong safety culture. Assist with development, implementation, and maintenance of company flight operations manuals, procedures, checklists, and training programs. Coordinate with maintenance personnel regarding aircraft availability, discrepancies, inspections, and operational readiness. Assist with operational planning as the Part 135 operation grows. Investigate and document operational incidents, irregularities, and safety concerns as appropriate. Ensure required FAA and company records are maintained accurately and timely. Maintain professional relationships with FAA personnel, customers, vendors, and aviation partners. Serve as Pilot in Command when assigned and appropriately qualified. Required Qualifications Previous experience serving as a Chief Pilot for a Part 135 operator. Minimum of 3 years of qualifying PIC experience under Part 135 or Part 121, consistent with applicable FAA requirements. Current FAA pilot certificate appropriate for the company's operation. Appropriate aircraft category, class, instrument, and type ratings as applicable. Qualified to serve as PIC in at least one aircraft used in the company's operation. Strong working knowledge of FAA regulations applicable to Part 135 operations. Demonstrated understanding of Part 135 operational control, safety, training, and compliance requirements. Strong leadership and communication skills. Excellent judgment and decision-making ability. Strong organizational skills and attention to detail. Ability to manage multiple operational priorities in a fast-paced environment. Must meet all applicable FAA, DOT, company, and regulatory requirements. What We're Looking For We're looking for an experienced aviation professional who can take ownership of the flight operation. This person needs to be comfortable balancing the operational demands of a growing aviation business with the regulatory and safety responsibilities of a Part 135 certificate. The Chief Pilot will have a significant role in establishing expectations for the pilot team, maintaining operational discipline, and ensuring that safety and compliance remain at the center of every flight. Prior Chief Pilot experience in a Part 135 environment is a key requirement for this position. Why Join BH Aviation? Leadership role within a growing aviation operation. Opportunity to help build and develop a Part 135 operation. Work with a family-owned company with diverse business operations. Professional aviation environment with a strong focus on safety and service. Competitive compensation and benefits package. Opportunity to fly as part of the position, as operationally appropriate. Located in Rapid City, with the Black Hills right outside your door. #riddles Scan to Apply Just scan this QR code to apply from your phone. Scan to Apply Not ready to apply yet? Enter your email and we'll send you a reminder to come back and apply. Remind Me Later Job Location Rapid City, South Dakota, 57703, United States Frequently asked questions about this position Similar Jobs In Rapid City, South Dakota Aircrew Scheduler Adams Communication & Engineering Technology, Inc. Ellsworth, South Dakota See Job Details