Senior Manager, Technology Delivery

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.

Full-time

We are seeking an experienced Senior Manager, Technology Delivery to lead complex software development and system integration initiatives, as well as ensure successful delivery of technology solutions. The ideal candidate will have deep knowledge of the Software Development Life Cycle (SDLC), experience working closely with development teams, and a proven ability to manage technical projects in an Agile environment. Experience in the airline industry is highly desirable.

The incumbent will be comfortable learning and adapting to the intricacies of the Tradewind environment, happy liaising with stakeholders at all levels, and keen to apply their years of expertise to plan, execute and deliver projects of all levels of complexity.

• Oversee the planning, execution, and delivery of large-scale projects from initiation to completion.
• Develop and manage project plans, timelines, budgets, and resource allocation.
• Ensure compliance with organizational standards, methodologies, and best practices.
• Identify and mitigate project risks, issues, and dependencies.
• Communicate project status, progress, and outcomes to stakeholders and executive leadership.
• Foster collaboration across departments and maintain strong vendor relationships.
• Drive continuous improvement in project management processes and tools.
• Provide positive, team-oriented collaboration and customer service with all internal and external stakeholders, project partners, and business users.
• Other duties as assigned.

• Bachelor’s degree (4-year degree) in Computer Science, Information Technology, Engineering, or related field.
• PMP (Project Management Professional) certification required.
• 10–15 years of progressive project management experience, with a strong technical focus.
• Proven experience managing software development projects and working with development teams.
• Hands‑on involvement in requirements gathering, sprint planning, and SDLC processes.
• Strong understanding of Agile and Waterfall methodologies.
• Excellent communication and leadership skills.
• Proficiency with project management and Agile tools (e.g., Azure Dev Ops, MS Project, Jira).

• Experience in the airline industry a plus.
• Familiarity with cloud platforms, APIs, and integration projects.
• Advanced degree (MBA or equivalent).

• Able to lift up to 60 lbs.
• Available to work weekends, holidays, and provide after‑hours accessibility to personnel and leadership.
• 50% travel required across the Northeast Region, Southeast Region, Bahamas and limited time in the Caribbean.
• Prolonged periods of desk work using a computer.
• Exposure to outdoor elements including heat, cold, rain, wind, and sun during ramp and operational duties.

• Comprehensive health and voluntary insurance plans
• Retirement plan with company match
• Paid time off
• Standby travel on select Tradewind Aviation scheduled flights
• Discounted standby travel benefits on numerous major and regional US and international airlines
• A rewarding career path with opportunities for growth and advancement throughout the organization

$120,000 - $150,000 per year