The Senior Conversation UX Designer will define and elevate how Liberates insurance customers interact with Liberate’s AI-powered agents. You will lead the design of conversational experiences that combine the precision of enterprise workflows with the fluidity of natural human dialogue.

This is a high-impact, cross-functional role that requires creativity, systems thinking, and a deep understanding of how language, tone, and context drive user trust. You’ll partner with Product, Engineering, and Customer Success to create scalable, intuitive AI interactions that deliver measurable business outcomes across the insurance ecosystem.

Location: Boston or San Francisco (Berkeley) hybrid role (2 days/week in-office)

Key Responsibilities

Conversation Experience Strategy & Design Leadership

• Lead the design of end-to-end conversational experiences across Liberate’s voice and chat AI products.

• Define frameworks for dialogue design, persona tone, and multimodal user interactions that scale across customers.

• Create conversation architectures that balance automation efficiency with empathy and compliance in insurance workflows.

• Partner with Product and AI Engineering to translate complex insurer requirements into elegant, human-centered conversational flows.

• Conduct user research and usability testing to measure comprehension, satisfaction, and business impact.

• Mentor junior designers and establish conversation design best practices and documentation standards.

Advanced Prompt Design & LLM Optimization

• Design, test, and optimize prompts for large language models (LLMs) to achieve high response accuracy, consistency, and contextual relevance.

• Develop reusable libraries of prompt templates and dialogue flows that align with Liberate’s product taxonomy.

• Collaborate with AI engineers to refine tone, structure, and interaction logic within the model.

• Analyze interaction data and feedback loops to continuously improve conversation design and AI performance.

• Lead internal experimentation around new prompt engineering techniques and model capabilities.

Cross-Functional Collaboration & Enablement

• Partner with Customer Success and Implementation teams to tailor conversational frameworks for each insurer’s environment.

• Collaborate with Product Marketing to ensure conversational tone aligns with Liberate’s brand voice and value propositions.

• Serve as the design voice in cross-functional planning — advocating for usability, empathy, and clarity in every AI interaction.

• Contribute to internal design systems, voice tone guides, and AI conversation standards.

Thought Leadership & Innovation

• Stay ahead of industry trends in conversational AI, UX writing, and generative design.

• Represent Liberate’s design expertise at industry events, conferences, and client workshops.

• Drive internal innovation projects exploring the intersection of user experience, AI, and human trust.

Qualifications

• 7+ years of experience in UX Design, Conversation Design, Content Design, or Interaction Design — including at least 2 years focused on conversational or AI-driven interfaces.

• Background in linguistics, human-computer interaction, cognitive psychology, or AI/NLP design.

• Proven experience designing scalable, human-like conversations for chatbots, voice assistants, or generative AI systems.

• Strong grasp of LLM behavior, prompt design, and the principles of natural language interaction.

• Exceptional communication and writing skills, with an ability to craft concise, empathetic dialogue for diverse user contexts.

• Experience partnering with engineering and product teams to deliver production-ready AI experiences.

• Strong analytical mindset, capable of using data and user feedback to refine conversation design.

• High ownership, creativity, and adaptability in a fast-paced, early-stage environment.

Nice to Have

• Experience in insurance, fintech, or regulated enterprise software.

• Proficiency with Figma, Voiceflow, Botmock, or conversation prototyping tools.

• Published work or portfolio showcasing conversation design and generative UX examples.

Benefits

• Competitive salary with equity options

• Flexible PTO

• 401(k) plan

• Comprehensive health, dental, and vision insurance

• Hybrid work environment with flexibility for remote days

• Collaborative, mission-driven culture focused on redefining insurance through AI