Supervisor of Operations
HybridDallas, Texas, United States
Job Summary
Lead the Vacation Planning Operations team by overseeing end-to-end booking processing from reservation creation through voyage close, ensuring accuracy across documentation, invoicing, and communications. Coach staff on performance and deliver training on new systems, AI tools, and updated workflows while managing irregular operations and redeployments. Partner with the AI & Technology team to support the deployment of AI-assisted workflows, identifying automation opportunities and translating system changes into team-ready training. Provide regular reporting on team performance and quality metrics to drive process improvements and throughput. This hands-on leadership role supports Windstar's contact center modernization, combining tactical oversight of daily booking operations with a forward-looking approach to technology integration and team development.
Required Qualifications
- 2+ years of contact center or reservations operations experience in roles of increasing responsibility
- Strong understanding of booking lifecycle operations, reservations systems, and post-booking processing workflows
- Proficiency with reservations and operations systems
- Strong written and verbal communication skills
- Excellent organizational and time management skills
- A proactive, solution-oriented mindset
- Deep familiarity with Windstar Cruises product, policy, and procedure (or the demonstrated ability to learn quickly)
- Full-time position available to work in a hybrid-model from Miami metro area, or remotely as long as you live in one of these states: AR, AZ, FL, LA, MN, TX, and WI
Desired Qualifications
- 1+ year of direct supervisory or team lead experience preferred
- Demonstrated experience managing teams with varied duties and skill levels
- Experience in the travel, hospitality, or cruise industry strongly preferred
- Experience with Seaware preferred
- Comfort working with AI-assisted tools and genuine curiosity about how technology can improve operational performance
- Prior experience with AI platforms, CRM automation, or workflow tools is a plus
- Intermediate to advanced proficiency in Microsoft Office (Excel, Word, Outlook, Teams), with the ability to train others on core usage
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