Lead AI Behavior Designer

Overview:

Join your favorite vacation-rental marketplace as a content leader raising the bar for guest and host interactions with AI customer support. You’re a writer first—in the past, you may have been called a conversation designer, a content designer, or a content strategist. Nowadays, you don’t just design for “the happy path”—a single right answer or carefully constructed dialog flow. You direct probabilistic AI systems to operate within a range of acceptable behaviors, safety guardrails, and nuanced brand guidelines. 

In this role, you’ll shadow our in-house lead for 2 months before taking the reins when they step out on 6-month leave. You’ll be expected to lead a team of 3 writers and work across product and engineering teams to ensure model output aligns with brand goals. It’s a portfolio-defining opportunity at an inclusive company that’s globally recognized for redesigning the way the world travels. 

The Details:

  • 8 month contract (1099 only)
  • Starts June 1, 2026
  • 40 hours per week

What You'll Do:

On a typical day, you might

  • Translate brand strategy into system prompts and logic gates that govern AI agent behavior
  • Define and measure model interactions; perform evals, fine-tune output, and build auto-rater agents
  • Provide vision, feedback and mentorship to a team of three conversation designers
  • Create “gold-standard” chat conversations and UI copy used to train models
  • Problem-solve with eng/PMs to ensure feasibility, implementation, and ideal UX

We're Looking for Someone with:

  • Understand and leverage model capabilities/dynamics to shape agent behavior
  • Be comfortable working with linguistic, psychological, and technological inputs
  • Maintain a flexible mindset; think systemically about desired behaviors and outcomes
  • Demonstrate pitch-perfect voice matching skills and tonal sensitivity
  • Have +10 years experience on product/UX teams
  • Have +7 years experience in conversation design
  • Have hands-on experience designing for generative and/or agentic AI
  • Navigate the tension between creative brand voice, safety, feasibility and compliance
  • Provide a portfolio showcasing AI and conversation design work (we understand AI projects are often under NDA; we're most interested in seeing your logic and design thinking on AI work)
  • Have bulletproof writing, editing, and proofreading skills
  • Master the manager's schedule: sync regularly with stakeholders while carving out deep-work blocks
  • Work during US business hours

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