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.
Responsibilities- 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.
Qualifications- 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.
