Director of Operations - New Haven, Connecticut

Company/Organization: Fly the Whale

Position: Pilot-Fixed Wing

Job Type: Permanent

Posted: 3/9/2026 8:23:46 PM

Description:

This is an opportunity with a successful aviation organization known for strong employee loyalty and a collaborative team environment.

This role is structured for a strong leader who appreciates stability, clear expectations, and the ability to step into a well-supported operation and lead it long-term.

Position Overview

The Director of Operations has overall authority and responsibility for managing the flight department, including operational control, compliance oversight, crew leadership, and coordination with maintenance and regulatory agencies.

Key Responsibilities

• Oversee Part 135 on demand and scheduled flight operations in compliance with FARs
• Execute policies and plans related to crew members, dispatchers, and operational control
• Coordinate and train check airmen
• Maintain oversight of aircraft movement and utilization through delegated personnel
• Oversee the Dispatch department, including day to day decision making together with Maintenance and Customer Service/Sales
• Oversight/development of the Safety Management System (SMS)
• Partner with Maintenance to align aircraft inspections and usage
• Maintain Operations Specifications, GOM, and essential manuals
• Ensure reporting and communication requirements with FAA and TSA
• Oversee FAR 119.59 record keeping
• Conduct or supervise company training programs
• If qualified, may occasionally fly to support operational oversight

What Makes This Role Appealing

• Well-established aviation organization with long-term stability
• Supportive, close-knit team culture
• Opportunity to own the role and provide steady leadership

Requirements

• Airline Transport Pilot Certificate
• 3 years of experience within the last 6 years as Pilot-in-Command under Part 121 or Part 135
• Minimum 3 years of management or supervisory experience
• Strong leadership presence and collaborative decision-making style
• Subject to pre-employment background check and motor vehicle report review
• Maintain valid driver's license and endorsements as required per position
• Subject to pre-employment physical, medical evaluation, and drug screen due to the safety sensitive nature of this position
• Knowledge & experience with Part 91/135 C208 Amphibian seaplane operations preferred but not required.

Job Type: Full-time
Pay: $140,000.00 - $165,000.00 per year, based upon experience 
Work Location: In person, New Haven, CT

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