Lead Conversational Designer

We are seeking a Lead Conversational Designer to help shape the future of enterprise conversational AI experiences. This role is ideal for someone who has evolved beyond traditional deterministic chatbot design and has hands‑on experience designing generative AI-powered conversational experiences using modern LLMs, prompt engineering, and agent‑based architectures.

As a Lead Conversational Designer, you will partner closely with Product Managers, Software Engineers, AI Engineers, UX teams, and other stakeholders to design intelligent conversational experiences across customer‑facing and internal enterprise products. You'll play a key role in helping mature our conversational design practice by introducing generative AI best practices, mentoring other designers, and helping define the next generation of our conversational architecture.

This is a highly collaborative role requiring someone who can bridge technical and non‑technical audiences, translate complex AI concepts into intuitive user experiences, and create conversational flows that are both engaging and compliant with enterprise standards.

Responsibilities

Lead the design of conversational experiences for AI‑powered chatbots, virtual assistants, and emerging AI agent solutions.

Design conversational flows that leverage both deterministic logic and probabilistic/generative AI capabilities.

Develop prompts, conversation strategies, and response frameworks that improve user experience and AI performance.

Partner closely with Product, Engineering, AI/ML teams, and UX stakeholders throughout the product lifecycle.

Collaborate with engineers to implement, test, iterate, and optimize conversational experiences.

Translate technical concepts such as prompt engineering, LLM behavior, retrieval, and AI orchestration into language that business stakeholders can easily understand.

Design conversation architectures that balance user experience, business objectives, compliance requirements, and technical feasibility.

Help establish conversational design standards, best practices, and governance across multiple products and business units.

Mentor and elevate other conversational designers by introducing generative AI design methodologies and modern conversational design principles.

Continuously analyze conversation performance and refine prompts, flows, and AI responses based on user behavior and feedback.

Support the development of new conversational AI architectures as the organization evolves beyond legacy chatbot frameworks.

Partner with cross‑functional teams supporting both customer‑facing and internal enterprise AI initiatives.

Design conversational experiences for new AI skills, capabilities, and agentic workflows.

Ensure conversational experiences align with accessibility, usability, compliance, and enterprise quality standards.

Required Qualifications

5–8 years of experience in UX, Conversation Design, Voice UX, Conversational AI, or related experience.

Strong experience designing conversational experiences for chatbots, virtual assistants, or AI assistants.

Experience designing conversational flows, dialogue structures, intents, prompts, fallback strategies, and user journeys.

Strong understanding of deterministic conversational design as well as probabilistic/generative AI interaction models.

Experience partnering directly with software engineers and technical development teams.

Ability to communicate effectively with both technical and non‑technical stakeholders.

Experience working cross‑functionally with Product Management, Engineering, UX, and AI teams.

Comfortable iterating prompts and conversational responses based on testing and performance data.

Ability to balance user experience, technical constraints, and business goals.

Preferred Qualifications

Experience designing AI agents, autonomous workflows, or multi‑agent conversational systems.

Familiarity with prompt engineering concepts and LLM behavior.

Exposure to conversational AI platforms and modern AI frameworks.

Experience helping define conversational design strategy or design systems.

Previous experience mentoring or leading other conversational designers.

Enterprise‑scale product experience supporting multiple business units.

Experience working in distributed, cross‑functional organizations.

Background working within regulated industries such as:

Insurance

Other highly regulated environments

Experience designing conversational experiences that must adhere to legal, compliance, privacy, and regulatory requirements.

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