Chief Pilot

We are seeking an experienced aviation leader to join a well-established aviation team as our current Chief Pilot retires. Based at our dedicated hangar facility at Hanscom Field in Bedford, Massachusetts, we operate three Gulfstream aircraft (two G650ER
s and a G500) in support of the company’s global business activity.

Our flight department is built around three priorities: safety, grounded in a just culture; providing a superior service experience in every facet of the department; and a continuous focus on operational excellence. The Chief Pilot leads the Flight Operations team and is responsible for ensuring our pilots are prepared, qualified, and supported to conduct safe, consistent, and effective aircraft operations. Serving as both a people leader and an active line pilot, the Chief Pilot works closely with the Director of Aviation and Aviation Leadership Team to provide operational oversight and maintain the standards and culture necessary to support these priorities and the department’s mission.

Responsibilities:

Team Leadership & Culture: Leads the Flight Operations (pilot) team, fostering a culture of trust, engagement, and shared accountability.

• Leads the Flight Operations team within Corporate Aviation.
• Fosters a culture of trust, respect, and open communication by modeling behavior that embodies Liberty Mutual's Identity and Values, remaining highly engaged with the pilot team, and soliciting input to keep a sharp focus on operational excellence.

Cross-Functional Coordination & Leadership Engagement: Represents Flight Operations within the Aviation leadership team, ensuring alignment across the department.

• Works closely with the Corporate Aviation leadership team — including attending and actively participating in Aviation Leadership Team / Safety Officer meetings — to ensure effective communication and coordination among all personnel groups in support of the department's goals and objectives.

Recruiting, Onboarding & Pilot Development: Partners with the Director of Aviation to build the pilot team, from hiring through onboarding.

• Works with the Director of Aviation to identify and hire captains and first officers.
• Responsible for onboarding, indoctrination, and training of new pilots.

Training & Qualification Standards: Establishes and maintains the training curriculum, qualification standards, and standardization program for all pilots.

• Establishes and periodically reviews the training curriculum and performance standards (safety, technical, and service) in coordination with the Director of Aviation and Aviation leadership team, ensuring pilots have the aircraft systems, equipment, and operating limitations knowledge necessary for safe operations on each assigned type, and that standards remain current with fleet, mission, and regulatory changes.
• Tracks and ensures pilots meet all training, qualification, and administrative requirements, including flight reviews, medical certificates, and recurrent training due dates.
• Establishes and manages pilot standardization processes to maintain consistency of training and evaluation across the pilot group.
• Leads pilot-side planning for fleet changes, including transition training and manual updates for new aircraft types.

Core Flight Operations Management:Oversees and supports daily flight operations.

• Serves as the pilot group's primary resource for day-to-day operational matters, including crew assignments aligned to departmental needs, qualifications, and mission requirements.
• Guides pilots on safety, technical, and service performance standards, working collaboratively to address deficiencies as they arise.
• Supports pilots in coordinating with Maintenance, Passenger Services, and Operations Support on daily operational matters,…