AI Experience Specialist

We started  to help maximize lives–both the lives of our customers and the lives of our team – so that everyone can experience all that life has to offer. For our employees, our promise is that  is more than just a job; it’s an opportunity to unlock one’s potential, where learning is celebrated and impact is realized.

We are more than a fast-paced, high-growth tech company; we care about our people and take career progression seriously. This is your career and our aim is to supercharge it through the people, the work, and the programs that fuel who we are.

Our mission is to make customer support easy and financially efficient. We are obsessed with reducing the time, contacts, and steps it takes to solve a customer’s problem or question, and believe that effective AI Support is the cornerstone to our success.

In this role, you'll shape the way we communicate and support our customers through our AI Agents—both chat and voice —across multiple channels and partners. You will own all things related to AI Agent communication, training, and experimentation, including playbook creation for both text-based chat flows and voice conversational design. You'll collaborate directly with cutting-edge AI partners to create and optimize playbooks that ensure customers receive clear, helpful, and consistent support regardless of whether they're chatting or calling.

This is a unique opportunity to blend communication strategy, AI playbook management, and data-driven insights to impact our North Star: customer satisfaction directly.

This role is part of the newly formalized, AI Agent Experience Team focused solely on the training, performance, and optimization of our AI Agents. We believe  Customer Support is positioned to lead the industry curve in AI Agent support coverage and capabilities. Through experimentation and listening to our customers' experiences, we advocate for continuous AI experience evolution and shape our partners’ roadmaps.

This team works closely across multiple Operations sub-functions - including Business Operations, Technical Account Management, and Engineering.

• Design, build, and continuously optimize AI chatbot playbooks and conversational flows.
• Monitor and analyze Chatbot performance (CSAT, resolution rates, deflection), identifying opportunities to improve resolution and customer experience.
• Collaborate with cross-functional teams to refine conversational design and ensure a smooth customer journey.
• Build clear documentation and escalation paths for when AI self-service cannot fully resolve a customer issue.
• Analyze bot feedback and performance trends to identify key drivers of satisfaction and friction.
• Translate feedback into actionable recommendations for AI product, operations, and support.

• Degree in Data Analytics, Communications, Marketing, Business, or a related field.
• Experience developing and optimizing chatbot playbooks and conversational flows, with an understanding of voice AI conversation design, including VUI principles, prompt engineering, and multi-turn dialogue management.
• Exceptional written and verbal communication skills, with experience writing and refining scripts for customer-facing AI across both chat and voice channels, including attention to conversational pacing and natural language patterns.
• Strong analytical skills with the ability to interpret CSAT, NPS, and chatbot performance data and turn them into actionable insights.
• Proficiency in CRM software and data analytics tools (e.g., Excel, Looker, Google Analytics) to extract insights and track bot performance.
• Hands‑on experience designing error recovery paths, escalation logic, and timeout handling for AI‑driven customer interactions.

• Hands‑on experience in AI chatbot management (e.g., Ada, Poly, Decagon, Intercom, Drift) or customer automation platforms.
• Exposure to travel, fintech, or SaaS industries.
• Knowledge of communication frameworks (e.g., neurolinguistic programming, Fogg Behavior Model).
• Strong project management skills with a proven ability to manage multiple priorities.

Work from anywhere in the…