Director of Scheduling and Dispatch

About Tradewind:

Tradewind Aviation is a leading Part 135 commuter and on-demand private charter operator with operational bases at the Waterbury/Oxford, CT (OXC), Westchester, NY (HPN), Stuart, FL (SUA) and San Juan, PR (SJU) airports. Founded by aviation enthusiasts in 2001 on the premise that all flights deserve the highest quality aircraft, crew, and service, Tradewind provides personal air travel—both private and scheduled service—throughout North America and the Caribbean. 

For more details visit www.flytradewind.com 

Position Overview

The Director of Scheduling & Dispatch is a senior operational leader responsible for managing and developing Tradewind's Scheduling and Dispatch teams of more than 20 operations professionals supporting both Charter and Scheduled Service. This individual ensures seamless day-to-day operational execution and efficient fleet utilization in a 24/7/365 environment. 

Acting as a key cross-functional leader, the Director coordinates extensively with Sales, Services, Crew Planning, Flight Operations, Maintenance, and other internal stakeholders. This role drives operational excellence, ensures regulatory compliance, and fosters a culture of continuous improvement, collaboration, and professional development. 

 Essential Functions

• Leadership & Team Management 
• Lead, coach, and mentor a team of 20+ Scheduling and Dispatch professionals across multiple shifts in a continuous 24/7/365 operation. 
• Establish clear performance expectations, development plans, and succession planning for all team members. 
• Drive a culture of accountability, communication, and proactive decision-making. 
• Oversee recruiting, onboarding, and ongoing training to ensure operational consistency and workforce readiness. 

Scheduling & Dispatch Oversight

• Direct all Scheduling and Dispatch activities for both Charter and Scheduled Service operations. 
• Ensure efficient flight scheduling, routing, and release in alignment with company standards and regulatory requirements. 
• Oversee day-of-operations decision-making to manage disruptions, weather events, maintenance issues, and customer needs. 
• Maintain high standards of customer service by ensuring timely communication and operational reliability. 
• Achieve all key financial metrics  

Fleet Management & Optimization

• Oversee daily fleet utilization planning and strategic annual fleet allocation to maximize aircraft productivity and commercial performance. 
• Partner with Maintenance and Flight Operations to ensure aircraft readiness, balanced usage, and minimal operational disruptions. 
• Track fleet availability, usage rates, and reliability metrics to inform business decisions. 

Cross-Functional Coordination

• Collaborate closely with Sales to support charter quoting, aircraft available checks, and operational feasibility assessments. 
• Work with Crew Planning to ensure proper crew pairing, legal compliance, and efficient staffing around operational needs. 
• Serve as a key liaison with Flight Operations and Maintenance to support safe, efficient, and coordinated execution across departments. 
• Participate in operational planning, contingency strategy, and long-term growth initiatives. 

Operational Excellence & Compliance

• Ensure all dispatch and scheduling functions comply with FAA regulations, company policies, and safety management protocols. 
• Develop and refine standard operating procedures (SOPs) for Dispatch and Scheduling. 
• Identify opportunities for process enhancement, system improvements, and technology upgrades. 
• Achieve all key financial metrics and on time performance targets through efficient fleet utilization, resource management, and operational decision-making. 
• Monitor operational KPIs and create reports for senior leadership. 

Qualifications

• 5+ years of experience in part 135 aviation operations, with at least 2 years in a people leadership role. 
• Prior experience in part 135 scheduling, strongly preferred. 
• Demonstrated ability to lead large, multi-shift teams in high-tempo environments. 
• Strong understanding of flight operations, crew regulations, and PC12 aircraft performance. 
• Exceptional communication, decision-making, and crisis-management skills. 
• Proven ability to collaborate across departments and drive organizational alignment. 

Additional Skills & Abilities

• Clear, confident communicator with strong leadership presence. 
• Highly organized, detail-oriented, and solutions-driven. 
• Comfortable navigating ambiguity and making quick, informed decisions. 
• Committed to developing people and building strong operational teams. 
• Passionate about aviation and delivering exceptional customer experience. 
• Ability to communicate effectively on the phone and in meetings (in person or virtual) 
• Other duties as assigned  

Physical Requirements

• Ability to lift / push or pull >or =15 lbs.? 
• Available to work weekends, holidays, and provide after-hours accessibility to personnel and leadership. 
• Ability to use to operate a computer keyboard, mouse, and standard office equipment 

Working conditions

• Prolonged periods of sitting at a desk, use of computers and office equipment 
• Indoor Office setting with standard lighting and temperature 

Benefits

• Competitive salary 
• Medical, Dental, Vision, FSA/DCA and 401(k) plan. 
• Paid vacation and sick days 
• Paid Parental Leave 
• Fun, dynamic team with opportunities for rapid advancement 
• Travel benefits through various US and International airlines