Generative AI Conversation Designer


The world's largest vacation rental marketplace is looking for a lead conversation designer to help integrate generative AI into their support chatbot.

Of course, there’s no playbook, no roadmap, and we’re all figuring this out as we go. But senior leadership has a vision, and we’re looking for someone who can translate that into an actionable plan. You don’t have to have all the answers, but you’re not afraid to play around, experiment, and bring a strong perspective on how we can tame this powerful new technology to do what we conversation designers have always done—design empathetic, people-friendly experiences.

The Details:

6-month contract (1099)

Competitive hourly rate

Full-time, 40 hrs./wk.

Team: 2 content designers + eng + product + legal

What You'll Do:

  • Shape how generative AI gets built into a personalized support experience.
  • Translate leadership’s strategic vision into a content design plan.
  • Run controlled experiments to identify gaps in content, train LLM voice, and ensure chatbot interactions generate trust in support contexts.
  • Define thoughtful guardrails and design principles for generative AI chatbot.
  • Train LLM to adopt an on-brand, contextually relevant tone of voice.
  • Generate and review prompts to ensure high-quality output.
  • Test interactions and continuously refine the chatbot experience.
  • Prepare LLM training data sets and benchmark responses.
  • Audit content taxonomy for opportunities to expand AI capabilities.

We're Looking for Someone with:

  • 7-12 years of experience designing conversational experiences for VUI, chatbots, IVR, or virtual assistants
  • Strong interest and perspective on generative AI and LLM required
  • Experience integrating generative AI preferred
  • Track record of working on emerging technologies
  • Proficiency with ChatGPT—you’ve been playing with it, studying resources and skilling up
  • Ability to navigate ambiguity
  • Strong writing and project management skills
  • Portfolio of conversation design projects

Apply for this role

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