Chief Pilot Jobs (NOW HIRING)

Alerion is looking for a Chief Pilot to join our Flight Operations Leadership Team.

The Chief Pilot serves as a key member of the Flight Operations leadership team and is responsible for the professional standards, regulatory compliance, operational readiness, and performance of all assigned flight crew within Alerion Aviation’s Part 135 operation. This role ensures safe, efficient, and compliant flight operations while supporting the company’s commitment to exceptional service delivery and operational excellence.

Reporting directly to the Director of Operations (DO), the Chief Pilot exercises delegated authority consistent with 14 CFR Part 119 requirements and provides daily operational leadership to the pilot group. The Chief Pilot champions a strong safety culture, supports strategic operational objectives, and ensures alignment with company values, FAA regulations, Operations Specifications, and Safety Management System (SMS) principles.

The Chief Pilot leads by example through visible engagement with crews, proactive communication, and consistent reinforcement of safety, professionalism, accountability, and customer service standards.

Regulatory Authority

The Chief Pilot exercises authority as defined under 14 CFR Part 119 and company delegation from the Director of Operations. The position is responsible for ensuring assigned flight crew operate in accordance with applicable regulations, company procedures, training requirements, and safety standards.

Leadership & Personnel Management

• Provide leadership, supervision, and direction to all assigned flight crew while fostering a culture of safety, professionalism, accountability, engagement, and service excellence
• Ensure pilot staffing levels support operational reliability, aircraft coverage, and business growth objectives
• Provide operational leadership coverage in the absence of the Director of Operations
• Maintain effective two-way communication with pilots through briefings, bulletins, meetings, and direct engagement
• Promote strong pilot morale and professional development across the flight operations department
• Support recruiting, interviewing, selection, onboarding, and retention of qualified flight crew
• Conduct performance evaluations and provide coaching, mentoring, and corrective guidance when required
• Participate in disciplinary actions in coordination with executive leadership and Human Resources
• Represent Flight Operations internally and externally with customers, regulators, airport authorities, and industry partners
• Support departmental initiatives that improve operational efficiency, standardization, and service quality
• Partner cross-functionally with Maintenance, Scheduling, OCC, Safety, Training, and Client Services to ensure coordinated operational execution.

Operational Oversight & Flight Crew Management

• Exercise delegated operational control responsibilities consistent with company policy and regulatory requirements
• Ensure flights are conducted in compliance with 14 CFR regulations, Operations Specifications, company manuals, and approved procedures
• Coordinate with Scheduling, Crew Planning, Maintenance Control, to ensure adequate crew coverage and operational continuity
• Monitor pilot utilization to ensure balanced workloads and regulatory compliance with flight and duty limitations
• Review and approve pilot schedules, training assignments, and time-off requests
• Ensure all assigned pilots are current, qualified, and properly trained prior to flight assignment
• Maintain oversight of pilot qualifications, currency tracking, and aircraft-specific authorizations
• Serve as Pilot-in-Command (PIC), check Airman, and/or Instructor Pilot when designated and as required to support operational needs
• Assist the Director of Operations in execution of the company Emergency Response Plan (ERP)

Training & Standardization

• Oversee development, implementation, and continuous improvement of pilot training programs
• Ensure compliance with Part 135 training requirements and company-approved training curricula
• Maintain standardization across fleets, crews, and operating practices
• Coordinate with Training Providers and internal Check Airmen to maintain training availability and effectiveness
• Monitor training performance trends and implement corrective or enhancement initiatives
• Support qualification program approvals, curriculum revisions, and regulatory submissions when required

Safety, Compliance & Regulatory Oversight

• Ensure full compliance with FAA regulations, Operations Specifications, company manuals (GOM, SOPs, Training Manuals), and internal policies
• Promote active participation in the company Safety Management System (SMS)
• Reinforce proactive reporting culture consistent with Just Culture principles
• Monitor flight operations to identify hazards, trends, and risk mitigation opportunities
• Support internal safety investigations and corrective action implementation
• Maintain a strong working relationship with the FAA Certificate Management Office (CMO)
• Represent Flight Operations during regulatory audits, inspections, and third-party evaluations (ARGUS, Wyvern, IS-BAO, internal audits)
• Ensure compliance with Drug & Alcohol Testing Program requirements and Pilot Records Database (PRD) obligations
• Maintain accurate pilot qualification records, training documentation, flight/duty records, and regulatory tracking systems
• Ensure operational manuals, checklists, and publications remain current, standardized, and compliant
• Support data-driven safety initiatives using FAA Data Collection Tools (DCTs) and internal performance monitoring programs.

Customer Experience & Operational Excellence

• Reinforce service expectations consistent with Alerion Aviation’s client experience standards
• Support pilots in balancing safety, compliance, and premium service delivery
• Assist in resolving operational service issues impacting customers or aircraft owners
• Represent Flight Operations during owner meetings and operational briefings when required

Strategic & Organizational Support

• Assist the Director of Operations in executing departmental strategy and operational initiatives
• Support fleet integration, aircraft transitions, and operational readiness planning
• Participate in audit preparation and continuous improvement initiatives
• Provide input into policy development, SOP revisions, and operational enhancements
• Support implementation of new technologies, procedures, and regulatory requirements

Required Qualifications & Experience

• Must meet Chief Pilot qualification requirements under 14 CFR §119.71
• Must meet all Alerion Aviation Pilot requirements.
• Airline Transport Pilot (ATP) Certificate required
• Type rating in at least one aircraft operated by the company preferred (or ability to obtain).
• Minimum 3,000 hours Total Flight Time
• Previous leadership experience within a Part 135 environment required
• Strong working knowledge of Part 119 and Part 135 regulatory framework
• Experience participating in FAA inspections, certificate management interactions, and regulatory compliance activities
• Experience supporting ARGUS, Wyvern, IS-BAO, or similar audit programs preferred
• Experience with FAA Data Collection Tools (DCTs) preferred
• Demonstrated ability to lead, mentor, and manage professional pilot teams
• Strong organizational, decision-making, and communication skills
• High attention to detail and strong commitment to procedural compliance
• Strong collaboration skills across Maintenance, Safety, Scheduling, and executive leadership teams
• Ability to support a 24/7 operational environment, including weekends and holidays when required
• Pass a DOT pre-employment drug test
• Pass a TSA required fingerprint-based criminal history records check in compliance with TSA Security Program Standards and 49 CFR 1544.229 and 49 CFR 1544.230
• Authority to work in the United States.

Preferred Qualifications:

• Check Airman experience
• Instructor Pilot experience
• 2,000 hours Multi PIC Time preferred
• Safety Management System (SMS) leadership involvement
• Prior experience supporting multi-fleet or geographically distributed operations
• Previous experience serving as Chief Pilot or Assistant Chief Pilot in a Part 135 operation

Alerion Aviation

Alerion Aviation is a boutique aircraft management company with one of the largest private fleets in South Florida. We specialize in hands-on service, personalized aircraft care, and a transparent, safety-first approach that has earned us Platinum Elite status — one of the rarest designations in private aviation.

Our team is what makes us different. With decades of collective experience, each member brings deep expertise, human-first, and total accountability to every client interaction. We offer:

• Medical: Company sponsors 100% premium for Employee and 50% premium for dependent on select plans
• Dental and Vision Plan options
• Group Life and AD&D
• Voluntary Life and AD&D
• 401(K) Retirement Plan and Match program
• Health Savings Account (HSA)
• Monthly Phone Allowance
• Employer Paid Known Crewmember Badging
• Paid Time Off