Chief Pilot & Flight Operations Leader

Liberty Mutual Fire Insurance Co.; Bedford (MA); On-site; USD 180,000 - 240,000; Full time

Job summary

Liberty Mutual Fire Insurance Co. is seeking an experienced Chief Pilot to lead our Flight Operations team at Hanscom Field, Bedford, MA.

The Chief Pilot will oversee safety, pilot development, and operational excellence while serving as a hands-on line pilot. You will partner with the Director of Aviation and the Aviation Leadership Team to maintain high standards across the department and ensure effective communication with Maintenance, Passenger Services, and Operations Support.

Qualifications

• Seasoned aviation leader with experience directing flight operations.
• Experience building training curricula and qualification standards.
• Proven ability to recruit, onboard, and develop pilots.
• Strong focus on safety culture and operational excellence.

Responsibilities

• Lead the Flight Operations team and foster trust and accountability.
• Represent Flight Operations within Aviation leadership and coordinate with partners.
• Oversee onboarding, indoctrination, and ongoing pilot development.
• Establish training curriculum, qualification standards, and standardization program.
• Maintain pilot training currency, medical certificates, and recurrent training due dates.
• Manage fleet transition planning, including new aircraft type training.
• Ensure day-to-day flight operations and crew assignments meet mission needs.
• Coordinate with Maintenance, Passenger Services, and Operations Support.
• Address regulatory factors like TFRs and NOTAMs in operations.
• Develop operating standards and procedures for flight operations.
• Keep department manuals and aircraft publications current.
• Communicate process changes to all affected personnel.
• Lead cross-functional engagement with Aviation Leadership Team and Safety Officer meetings.

Skills

Leadership

Aviation operations

Team development

Safety culture

Cross-functional collaboration

Training & qualification

Job description

Liberty Mutual Fire Insurance Co. is seeking an experienced Chief Pilot to lead our Flight Operations team at Hanscom Field, Bedford, MA.

The Chief Pilot will oversee safety, pilot development, and operational excellence while serving as a hands-on line pilot. You will partner with the Director of Aviation and the Aviation Leadership Team to maintain high standards across the department and ensure effective communication with Maintenance, Passenger Services, and Operations Support.