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CheckrCheckrDenver, CO

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.

82k – 112k
Hybrid3+ YOEProduct Design

About the role

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 AIPrompt EngineeringNluNLPChatbot AdministrationConversation DesignIntent MappingUtterance TrainingAnalyticsCross-Functional Collaboration

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