AI Enabled Executive Assistant

About the job

ob Description: AI Enabled Executive Assistant Key Responsibilities1. Reservation Operations & Pipeline Monitoring* Monitor incoming reservations and ensure each booking moves smoothly through the reservation pipeline.* Coordinate with operators/partner companies to confirm availability, booking details, changes, and operational readiness.* Keep guests updated on availability, next steps, payment status, booking confirmations, and any changes to their reservation.* Track reservation issues such as operator non-availability, maintenance concerns, boat changes, schedule conflicts, missing information, or delayed responses.* Escalate urgent or unclear issues to the right internal team member while keeping the guest/operator informed.* Maintain clean notes, status updates, and reservation records so the team always has visibility on what is pending, resolved, or at risk.2. AI-Agent Monitoring & Human-in-the-Loop Troubleshooting* Monitor AI-agent-driven reservation communication to ensure automated guest/operator conversations are progressing correctly.* Review flagged conversations, failed loops, incomplete responses, or exceptions where the AI agent requires human intervention.* Step in quickly when automation cannot resolve an issue and communicate clearly with the guest, operator, or internal team.* Identify repeated AI workflow gaps and document where the process can be improved, simplified, or better automated.* Use sound judgment when relying on AI outputs; verify information before acting and avoid blindly depending on automated responses.3. Guest, Customer & Operator Communication* Handle guest, customer, and operator communication with professionalism, empathy, patience, and cultural awareness.* Ensure guests feel heard, supported, and confident throughout the reservation and travel coordination process.* Respond to inquiries, clarify details, follow up on pending responses, and provide timely updates where required.* Maintain a warm, clear, customer-friendly tone across email, chat, CRM/ticketing systems, and internal communication channels.* Support a strong customer experience by preventing small issues from becoming escalations.4. AI-Assisted Research & Operational Support* Use AI tools such as ChatGPT, Claude, Gemini, Perplexity, or similar platforms to conduct structured research and prepare summaries.* Support research related to travel/tourism operations, customer pain points, operator requirements, payment systems, country-specific rules, foreign exchange, tax considerations, terms and conditions, and internal process questions.* Review online communities, travel forums, social conversations, competitor activity, and market signals to understand customer/operator needs.* Turn research into clear, concise, actionable notes for the founder/leadership team.* Verify AI-generated research through reliable sources, documentation, and credible references.6. AI Tool Adoption, Process Improvement & Future Team Support* Continuously look for ways to improve personal productivity, communication quality, research output, and task execution using AI tools.* Create or improve simple workflows, checklists, templates, prompts, SOPs, and escalation steps for reservation operations.* Demonstrate curiosity and a self-learning mindset: research, test, experiment, and figure out solutions instead of waiting for step-by-step instructions.* Support future scaling of concierge/reservation agents by documenting workflows and helping create repeatable processes.* Be comfortable growing into a coordination or supervisory support role as reservation volume and customer service coverage expand.Required Skills & Qualifications* Prior experience as an Operations Assistant, Reservation Coordinator, Customer Support Specialist, Executive Assistant, Virtual Assistant, Travel/Hospitality Coordinator, or Founders Assistant.* Hands-on AI tool proficiency is required; candidates should be able to demonstrate practical use of ChatGPT, Claude, Gemini, Perplexity, or similar tools through certifications, AI course credentials, prompt examples, workflow samples, case studies, or a small portfolio of AI-enabled work.* Strong written and verbal communication skills, especially for guest/customer/operator communication.* High attention to detail with the ability to track many moving reservations, conversations, and follow-ups at once.* Experience with ClickUp, ticketing systems, CRM tools, shared inboxes, or operational dashboards is strongly preferred.* Strong research ability with the judgment to verify AI-generated information before using it.* Comfortable working in a fast-moving startup or scaling business environment where processes may evolve quickly.* Proactive problem-solver who can learn independently, watch tutorials, research solutions, test ideas, and improve the way work is done.* Ability to communicate with empathy, patience, cultural awareness, and professionalism across different geographies and customer types.* Ability to manage confidential information and customer details with discretion. US shiftSalary- 4-4.2 LPA