Skip to content
CheckrCheckr

AI Conversation Designer

Design, optimize, and manage conversational AI agents across modalities, owning the full lifecycle from prompt engineering to deployment and performance tuning. Requires 3-5 years of hands-on experience with conversational AI platforms and strong analytical skills.

About the job

What you’ll do

  • Lead the development, optimization, and ongoing management of conversational AI agents across modalities, ensuring consistent performance and user experience.
  • Own the end-to-end lifecycle of assigned AI agents, including prompt engineering, conversation design, testing, and deployment.
  • Drive measurable improvements in agent performance through analysis of key performance indicators and conversation analytics.
  • Partner with cross-functional teams to identify automation opportunities and implement solutions that reduce contact volume while maintaining service quality.
  • Develop and maintain comprehensive documentation for AI agent workflows and processes.
  • Monitor and troubleshoot AI agent behavior, diagnosing issues across conversation flows and escalating technical issues as needed.
  • Implement and iterate on dynamic response content, including conditional logic, personalization, and multimedia elements within conversational interfaces.
  • Lead special projects as required to support evolving AI capabilities and business needs.

What you bring

  • 3-5 years of experience in conversational AI, knowledge management, chatbot administration, or similar roles managing customer-facing digital channels.
  • Hands-on experience with conversational AI platforms and understanding of NLU/NLP concepts.
  • Proficiency in conversation design principles, including intent mapping, utterance training, and fallback strategies.
  • Strong analytical skills with the ability to interpret conversation logs, performance dashboards, and customer feedback to drive optimization.
  • Excellent written communication skills and ability to craft clear, concise bot responses for diverse audiences.
  • Proven ability to collaborate cross-functionally and translate business requirements into actionable solutions.
  • Comfort navigating ambiguity and managing multiple priorities in a fast-paced environment.
  • An A-player mindset with a strong bias for action: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcomes.

What We Offer

  • A fast-paced and collaborative environment
  • Learning and development allowance
  • Competitive cash and equity compensation, and opportunity for advancement
  • 100% medical, dental, and vision coverage
  • Up to $25K reimbursement for fertility, adoption, and parental planning services
  • Flexible PTO policy
  • Monthly wellness stipend

Skills

Conversational AI, Prompt Engineering, Nlu, NLP, Chatbot Administration, Conversation Design, Intent Mapping, Utterance Training, Analytics, Cross-Functional Collaboration

Bestow

Bestow

United States

Product Designer II, Agent Experience
$108k+/yrRemote3+ YOEProduct Design

Product Designer II will own end-to-end design for agent, wholesaler, and back-office workflows, from research and problem framing through coded prototyping and implementation. The role requires 3–5 years of product design experience, strong Figma and research skills, and hands-on experience designing in code-based environments.

WorkWave

WorkWave

United States

Product Designer
$125k+/yrRemote4+ YOEProduct Design

Product Designer creating intuitive, accessible digital experiences for non-technical service professionals. The role owns design from discovery through delivery, partners closely with product and engineering, conducts user research, and requires 4+ years of experience plus a strong portfolio.

Assembled

Assembled

New York, NY

Product Designer, Platform Teams
$130k+/yrOn-site3+ YOEProduct Design

Designs intuitive, data-rich B2B software for support operations, including workflows for AI agents, analytics, planning, and configuration. The role requires 3+ years of production product design experience, strong systems and interaction design, customer research, and close partnership with product and engineering.

Assembled

Assembled

San Francisco, CA

Product Designer, Design Systems
$130k+/yrOn-site5+ YOEProduct Design

Leads the design system for a B2B product, defining visual foundations, reusable interaction patterns, documentation, and governance across teams. The role requires strong visual craft, systems thinking, Figma expertise, frontend collaboration, and interest in AI-native design workflows.

Counsel Health

Counsel Health

Boston, MA
Product Designer
$135k+/yrHybrid3+ YOEProduct Design

Design end-to-end consumer healthcare experiences across mobile and web, establishing visual, interaction, and motion standards for a trusted AI-enabled care product. Requires 3+ years of consumer product design experience, strong visual and interaction craft, and technical prototyping fluency.