Entry Level Pilot Jobs in Homestead, FL (NOW HIRING)

Awarded World's Best Small Ship Cruise line, Windstar Cruises is known for intimate yacht style experience and unique voyages to the world's best small ports and hidden harbors. Its three sailing yachts and four all-suite yachts carry just 148 to 342 guests and cruise around the world. Our mission is to imagine and deliver personalized and immersive experiences 180 degrees from ordinary. We enrich people's perspective through inspired travel.

Our Mission: Enriching Lives Through Travel

Our Values: Guest Obsessed, Open and Inviting, Fun-Loving and Focused, Light-Hearted and Genuine, Casual Yet Polished, Safe and Responsible.

Job Summary:

 The Contact Center AI Lead supports the Training Supervisor in the day-to-day administration and upkeep of Windstar Cruises' contact center AI platform. This role is a hands-on contributor responsible for maintaining the accuracy, quality, and effectiveness of AI-assisted tools used across the full Vacation Planning team. In addition to internal platform support, the Contact Center AI Lead shares co-ownership with the Chat Lead of the guest-facing virtual agent, monitoring its performance, maintaining its content, and ensuring it consistently delivers an experience that reflects Windstar's brand standard. The Contact Center AI Lead is also a standing participant in the company's broader AI initiatives, providing operational insight and front-line perspective as new capabilities are evaluated, piloted, and deployed across the contact center.

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.

•  Assist the Training Supervisor with the ongoing administration of the contact center AI platform, executing content updates, scripting revisions, and configuration changes as directed.
• Maintain AI knowledge bases, response libraries, and escalation logic to ensure accuracy across the full range of guest inquiries handled by the Vacation Planning team.
• Serve as a first-line resource for agents across the contact center who have questions about AI tool functionality, escalating platform issues to the Training Supervisor as needed.
• Coordinate with the Training Supervisor and technology partners to log, prioritize, and follow up on platform issues or enhancement requests.
• Co-own the performance and content of the guest-facing virtual agent alongside the Chat Lead, ensuring the tool delivers accurate, on-brand responses that reflect Windstar's guest experience standard.
• Monitor virtual agent interactions for accuracy, tone, escalation behavior, and guest experience quality; surface issues and coordinate corrections with the Training Supervisor and Chat Lead.
• Maintain and update virtual agent content in response to itinerary changes, policy updates, promotional launches, and seasonal shifts in guest inquiry patterns.
• Partner with the Chat Lead to review guest feedback and chat data, translating insights into scripting improvements and escalation logic refinements.
• Participate actively in ongoing AI initiatives across the contact center, including tool evaluations, pilot programs, and capability expansions, providing operational perspective and front-line feedback.
• Support the testing and documentation of new AI features or platform enhancements prior to team-wide rollout.
• Help identify opportunities where AI tooling could further support team efficiency, guest experience, or compliance and bring those ideas forward to the Training Supervisor.
• Stay current on developments in contact center AI, virtual agent technology, and hospitality industry applications to inform ongoing improvement efforts.
• Monitor AI-assisted interactions across all contact center functions, flagging errors or recurring performance gaps to the Training Supervisor for review and action.
• Assist with tracking and compiling AI performance data, including interaction volumes, escalation rates, and resolution accuracy, to support the supervisor's reporting to leadership.
• Help develop and maintain agent-facing job aids, quick-reference guides, and training materials related to AI tool use across all roles in the department.
• Provide cross-functional support across Training, QA, and AI functions, including cross-training and serving as backup coverage for aligned roles as needed.
• Other duties as assigned.

• Demonstrated proficiency with large language models (LLMs) and AI tools in a practical, hands-on capacity; this is a non-negotiable requirement.
• Entry-level candidates with demonstrated AI fluency and relevant project or coursework experience are encouraged to apply.
• Working understanding of how LLMs generate responses, handle context, and can be guided through prompting - able to apply this knowledge to evaluate AI output quality and identify where responses break down.
• Experience using AI tools in a professional or applied context, such as drafting and refining prompts, reviewing AI-generated content for accuracy and tone, or testing AI-assisted workflows.
• Familiarity with virtual agent or chatbot platforms, conversational AI tools, or contact center AI products; prior experience administering or maintaining such systems is a strong plus.
• Strong attention to detail with the ability to catch errors in AI-generated content that a less-experienced reader might miss, including tone mismatches, factual inaccuracies, and escalation of logic gaps.
• Clear written communication skills; able to draft scripts, update knowledge bases, and produce agent-facing materials that are accurate, concise, and on-brand.
• Collaborative and support-oriented by nature; this role is built around enabling others, and the right candidate finds satisfaction in making tools, teams, and processes work better.
• Proactive and curious; stays current on AI developments, asks good questions, and brings ideas forward without needing to own the outcome.

Benefits:

For full-time employees, Windstar offers a comprehensive benefits package including: Medical, Dental & Vision; HSA & FSA; Life & Disability; Accident, Hospital & Critical Illness; Pet Insurance; Vacation, Sick Time and paid Holidays; 401(k) with Company Match; Employee Assistance Plan; Education Assistance and Employee Discounts & Travel Deals.

EEO: 

Windstar is committed to a diverse and inclusive workplace. We are an equal opportunity employer. Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, pregnancy, genetic information, protected veteran status, or any other legally protected status.