Conversational UX Designer

📍 Job Overview

Job Title: Conversational UX Designer

Company: Five9

Location: United States (Remote)

Job Type: Full-Time

Category: Conversational AI / UX Design

Date Posted: 2026-02-19

Experience Level: Mid-Level (4+ years)

Remote Status: Fully Remote (for candidates outside 50-mile radius of San Ramon, CA) / Hybrid (3 days/week in office for candidates within 50-mile radius of San Ramon, CA)

🚀 Role Summary

• Design and develop cutting-edge AI-driven conversational experiences for both voice and chat channels, focusing on enhancing customer experience and optimizing operational efficiency.

• Translate complex business requirements into detailed technical specifications and clear solution designs for development teams, utilizing industry-standard documentation tools.

• Champion customer needs and best practices by guiding clients through solution implementation and continuous improvement within a customer-facing capacity.

• Stay at the forefront of AI and conversational technology by monitoring industry trends, vendor roadmaps, and integrating emerging capabilities into enterprise solutions.

📝 Enhancement Note: This role sits within the AI Automation and Solutions team, indicating a focus on leveraging artificial intelligence to create scalable and efficient customer interaction solutions. The emphasis on both voice and chat implies a need for a broad understanding of multi-channel conversational design.

📈 Primary Responsibilities

• Lead the end-to-end conversation design process for AI-driven solutions, from initial requirement gathering with stakeholders to detailed specification documentation.

• Facilitate cross-functional collaboration, effectively translating abstract business objectives into concrete technical specifications for engineering and development teams.

• Create comprehensive and clear solution designs and documentation using tools like Lucidchart and Voiceflow, ensuring alignment and understanding across all project participants.

• Actively engage with customers in a consulting capacity, providing expert guidance on best practices for conversational AI implementation and championing their needs internally.

• Proactively research and integrate emerging technologies, such as Large Language Models (LLMs) and advanced analytics techniques, to continuously enhance the capabilities of conversational AI solutions.

• Monitor and analyze industry trends and vendor product roadmaps to identify opportunities for innovation, strategic growth, and competitive advantage in the conversational AI landscape.

• Manage multiple customer engagements and projects simultaneously, balancing competing priorities while consistently delivering high-quality, best-in-class conversation designs.

📝 Enhancement Note: The core responsibilities highlight a blend of strategic design, technical documentation, customer consulting, and continuous innovation, all within the context of conversational AI. The expectation to manage multiple customers simultaneously points towards a need for strong project management and prioritization skills.

🎓 Skills & Qualifications

Education:

Experience:

• A minimum of 4 years of progressive experience specifically in Conversation Design or a similar role focused on crafting user-centric conversational interfaces.

Required Skills:

• Expertise in Conversation Design principles and best practices for both voice and chat interactions.

• Proficiency in requirement gathering and translating business needs into detailed technical specifications.

• Demonstrated experience with documentation tools such as Lucidchart and Voiceflow for clear solution design and process mapping.

• Hands-on experience with Large Language Models (LLMs), including prompt engineering, fine-tuning, and evaluation methodologies.

• Strong customer-facing skills, including consulting, best practice guidance, and effective stakeholder management.

Preferred Skills:

• Experience with AI Automation platforms and enterprise-grade contact center solutions.

• Familiarity with analytics techniques to measure and optimize conversational AI performance.

• Understanding of operational efficiency metrics and how conversational AI contributes to them.

• Knowledge of vendor roadmaps and emerging trends within the conversational AI and CCaaS (Contact Center as a Service) markets.

📝 Enhancement Note: The required 4+ years of experience combined with a graduate degree suggests a mid-to-senior level role. The specific mention of LLMs, prompt engineering, and fine-tuning indicates a focus on more advanced conversational AI capabilities beyond basic chatbot design. Customer-facing experience is a critical requirement, emphasizing the consultative nature of the role.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrate end-to-end conversation design projects, showcasing the evolution from initial concept to deployed solution.

• Include case studies that highlight specific examples of translating business requirements into functional conversational flows for voice and chat.

• Showcase documentation samples, such as flow diagrams created in Lucidchart or prototypes built in Voiceflow, illustrating clarity and detail.

Process Documentation:

• Provide examples of detailed technical specifications and design documents created for AI-driven conversational solutions.

• Showcase your approach to documenting user journeys, error handling, and escalation paths within conversational interfaces.

• Include examples of how you have used analytics to inform design iterations and measure the success of conversational AI implementations.

📝 Enhancement Note: For a Conversational UX Designer role, a portfolio is crucial. It should not just showcase aesthetic design but also the logical structure, technical feasibility, and measurable impact of the conversational experiences designed. Emphasis on tools like Lucidchart and Voiceflow, along with LLM experience, should be evident.

💵 Compensation & Benefits

Salary Range: $135,000 - $250,000 USD per year.

Benefits:

• Comprehensive health, dental, and vision coverage, with Five9 covering 100% of the employee portion of premiums.

• Generous employer contribution towards dependent costs for health, dental, and vision plans.

• Short-Term and Long-Term Disability insurance.

• Basic Life Insurance coverage.

• 401k savings plan with employer matching contributions.

• Access to an innovative mental health support platform offering personalized care, therapy, coaching, and mindfulness resources for employees and dependents.

• Generous Employee Stock Purchase Plan (ESPP).

• Paid Time Off (PTO) for rest and rejuvenation.

• Company-paid holidays.

• Paid volunteer hours to support community initiatives.

Working Hours:

• Standard full-time work hours, typically 40 hours per week.

• Flexibility may be available depending on project needs and team coordination, especially given the remote and hybrid nature of the role.

📝 Enhancement Note: The salary range is competitive for a specialized UX role with significant AI and customer-facing components in the US market. The benefits package is robust, with a strong emphasis on health and well-being, including extensive coverage and mental health resources, reflecting a commitment to employee welfare. The hybrid work requirement for those near San Ramon suggests a need for structured in-office collaboration days.

🎯 Team & Company Context

🏢 Company Culture

Industry: Cloud Contact Center Software (CCaaS) / Artificial Intelligence / Customer Experience Technology. Five9 is a leader in transforming customer service through cloud-based solutions.

Company Size: Over 1,000 employees (based on typical Five9 company profiles). This indicates a mid-to-large-sized organization with established processes but still retaining agility.

Founded: 2001. With over two decades of operation, Five9 has a strong market presence and a history of innovation in the cloud contact center space.

Team Structure:

• The Conversational UX Designer likely sits within the AI Automation and Solutions team, a specialized group focused on developing and implementing advanced AI technologies for customer interactions.

• This team may report into a broader Product, Engineering, or Solutions organization, with potential for direct collaboration with Sales, Professional Services, and Customer Success teams.

Methodology:

• Emphasis on a data-driven approach to design, using analytics to inform iterations and measure the impact of conversational AI solutions.

• Agile methodologies are likely employed for software development and solution deployment, requiring iterative design and feedback loops.

• A strong focus on customer-centricity, ensuring that designs meet user needs and deliver exceptional experiences while achieving business objectives.

Company Website: https://www.five9.com/

📝 Enhancement Note: Five9's position as a leader in cloud contact centers means this role is at the intersection of AI, customer service, and cloud technology. The company's established history suggests a stable environment with opportunities for impactful work on enterprise-level solutions. The "team-first culture" and celebration of diversity are key cultural indicators.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a specialist or senior individual contributor within the Conversational AI/UX domain. It requires deep expertise in conversation design, LLMs, and customer-facing consulting.

Reporting Structure: The designer will likely report to a Manager or Director of AI Solutions, Conversational Design, or Product Management within the AI Automation team. They will collaborate extensively with internal teams and external clients.

Operations Impact: This role directly impacts customer satisfaction, operational efficiency, and revenue generation by designing solutions that improve customer interactions, reduce service costs, and drive adoption of AI technologies within client contact centers.

Growth Opportunities:

• Specialization: Deepen expertise in specific AI domains (e.g., advanced LLM applications, voice biometrics, sentiment analysis) or specific industries.

• Leadership: Transition into a lead designer role, mentoring junior designers, or move into management positions overseeing conversational AI strategy and teams.

• Product Management: Leverage design and customer insights to move into product management roles focused on defining the roadmap for conversational AI features and platforms.

• Solutions Architecture: Grow into a solutions architect role, focusing on the broader technical implementation and integration of AI solutions within complex enterprise environments.

• Professional Services/Consulting: Advance within customer-facing roles, taking on more complex client engagements and strategic advisory positions.

📝 Enhancement Note: The combination of deep technical skills (LLMs, prompt engineering) and customer-facing consulting experience positions this role as a valuable contributor with significant growth potential. The company's focus on innovation within the CCaaS space provides fertile ground for career advancement.

🌐 Work Environment

Office Type: The role is described as "fully remote" for candidates outside a 50-mile radius of San Ramon, CA, and "hybrid" (3 days/week in office) for those within that radius. This suggests a modern, flexible work environment that accommodates both remote collaboration and in-person interaction.

Office Location(s): While remote-first for many, the hybrid requirement points to a physical office presence in or near San Ramon, California, likely equipped for collaborative work, client meetings, and team synergy.

Workspace Context:

• For remote employees, a dedicated home office setup conducive to focused work and video conferencing is expected.

• For hybrid employees, the office environment is likely designed to foster collaboration, with meeting rooms, shared workspaces, and access to company resources.

• The role involves extensive use of digital collaboration tools (e.g., Slack, Microsoft Teams, Zoom) for communication and project management.

Work Schedule:

• Standard business hours (e.g., 9 AM - 5 PM in a relevant time zone) are generally expected, but flexibility may be offered to accommodate global customer interactions or personal needs, especially for fully remote employees.

• The hybrid model requires adherence to specific in-office days (Monday, Wednesday, Thursday) for those within the 50-mile radius of San Ramon.

📝 Enhancement Note: The dual approach to work arrangements (fully remote vs. hybrid) caters to a broader talent pool while still valuing in-person collaboration for those geographically closer to a key office. This indicates a company that has adapted to modern work trends.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter or hiring manager will review your application and resume, focusing on experience with conversation design, LLMs, and customer-facing roles.

• Technical/Portfolio Review: Expect a deep dive into your portfolio. This may involve a dedicated session where you present 1-2 key projects, explaining your design process, the challenges faced, the solutions implemented, and the outcomes achieved, particularly focusing on your LLM and documentation skills.

• Behavioral & Situational Interviews: Interviews will assess your ability to handle customer interactions, collaborate with cross-functional teams, stay current with technology, and manage multiple priorities. Be prepared to discuss specific examples from your experience.

• Hiring Manager Interview: A final discussion with the hiring manager to assess overall fit, strategic thinking, and alignment with the team's goals.

Portfolio Review Tips:

• Curate Selectively: Choose projects that best demonstrate your expertise in conversational AI, LLMs, prompt engineering, and documentation (Lucidchart, Voiceflow).

• Showcase Impact: For each project, clearly articulate the business problem, your role, the design decisions made, the technologies used (especially LLMs), and the measurable results (e.g., improved containment rates, reduced handling times, enhanced customer satisfaction).

• Detail Process: Explain your step-by-step approach, from requirement gathering and user research to design, prototyping, testing, and iteration.

• Highlight LLM Application: Specifically detail how you've used LLMs, prompt engineering, and fine-tuning to create more sophisticated and effective conversational experiences.

• Documentation Clarity: Include examples of your documentation (flowcharts, specifications) to showcase your ability to communicate complex designs clearly.

Challenge Preparation:

• Be prepared for potential design exercises or case studies, either as part of the interview or as a take-home assignment. These might involve designing a conversational flow for a specific customer scenario or refining an existing one.

• Practice articulating your design rationale concisely and persuasively, focusing on the "why" behind your choices.

• Think about how you would approach gathering requirements from a hypothetical client and translating them into a conversational strategy.

📝 Enhancement Note: The emphasis on a portfolio and specific tools like Lucidchart and Voiceflow, along with LLM experience, indicates that candidates will be thoroughly vetted on their practical design and technical skills. The customer-facing aspect means interviewers will look for strong communication and consulting abilities.

🛠 Tools & Technology Stack

Primary Tools:

• Conversation Design Platforms: Voiceflow (explicitly mentioned), potentially others like Botpress, Rasa, or custom internal tools.

• Diagramming & Documentation: Lucidchart (explicitly mentioned), Visio, Miro, Figma for flow design and documentation.

• AI/ML Frameworks & Technologies: Large Language Models (LLMs) (e.g., GPT variants, BERT), prompt engineering techniques, fine-tuning methodologies, model evaluation frameworks.

• Collaboration & Communication: Slack, Microsoft Teams, Zoom, Google Workspace.

Analytics & Reporting:

• Familiarity with analytics platforms used in contact centers or conversational AI (e.g., Five9's own analytics suite, Google Analytics, specialized chatbot analytics tools) for performance monitoring and optimization.

CRM & Automation:

• While not explicitly stated as a primary tool for this role, understanding how conversational AI integrates with CRM systems (like Salesforce, ServiceNow) and broader automation workflows is beneficial.

• Knowledge of APIs and integration concepts can be advantageous.

📝 Enhancement Note: The explicit mention of Voiceflow and Lucidchart indicates these are key tools for the role. A strong understanding of LLMs, prompt engineering, and model evaluation is critical, suggesting the company is working with advanced AI capabilities. Familiarity with contact center analytics is also important for measuring success.

👥 Team Culture & Values

Operations Values:

• Customer Obsession: A core value, driving the need for designers to champion customer needs and deliver exceptional experiences.

• Innovation: Encouraging the exploration and integration of new technologies, like LLMs, to stay ahead in the AI and CCaaS market.

• Teamwork: Fostering a collaborative environment where individuals support each other, share knowledge, and work towards common goals.

• Accountability: Taking ownership of designs, projects, and customer success, ensuring high-quality delivery and measurable impact.

• Integrity: Upholding ethical standards in design, data handling, and customer interactions.

Collaboration Style:

• Cross-functional: Expect close collaboration with product managers, engineers, sales, and customer success teams to ensure alignment and successful implementation of conversational solutions.

• Consultative: A proactive and consultative approach is key when working with both internal stakeholders and external clients, offering expertise and guidance.

• Iterative: Embracing an iterative design process, incorporating feedback from stakeholders, customers, and performance data to continuously improve solutions.

• Knowledge Sharing: Encouraging the sharing of best practices, learnings from new technologies, and insights gained from customer engagements.

📝 Enhancement Note: Five9's emphasis on "team-first culture" and diversity suggests a supportive and inclusive environment. The values of customer obsession and innovation directly align with the responsibilities of a Conversational UX Designer focused on cutting-edge AI solutions.

⚡ Challenges & Growth Opportunities

Challenges:

• Rapidly Evolving AI Landscape: Keeping pace with the swift advancements in LLMs, AI ethics, and conversational technologies requires continuous learning and adaptation.

• Balancing Technical Sophistication with User Experience: Designing complex AI interactions that are intuitive, natural, and easy for end-users to navigate.

• Managing Multiple Client Demands: Simultaneously handling diverse client needs, project timelines, and stakeholder expectations across various engagements.

• Translating Abstract Concepts: Effectively communicating intricate AI concepts and design decisions to non-technical stakeholders and clients.

• Measuring ROI for Conversational AI: Quantifying the business value and impact of designed solutions, demonstrating tangible benefits to clients.

Learning & Development Opportunities:

• Advanced AI/LLM Training: Opportunities to deepen expertise in prompt engineering, fine-tuning, AI ethics, and emerging AI models.

• Industry Certifications: Pursuing certifications in UX design, conversational AI, or specific platform technologies.

• Cross-Disciplinary Exposure: Learning from AI engineers, product managers, and customer success professionals to gain a holistic understanding of the CCaaS ecosystem.

• Client Engagement Skills: Developing advanced consulting and presentation skills through direct client interaction and mentorship.

• Leadership Development: Potential pathways into lead designer, team lead, or management roles within the AI Solutions team.

📝 Enhancement Note: The challenges are inherent to working at the cutting edge of AI and customer experience. The growth opportunities are substantial, offering paths for both deep technical specialization and broader leadership within a growing technology company.

💡 Interview Preparation

Strategy Questions:

• "Describe a complex conversational AI solution you designed using LLMs. What was the business problem, your design process, the specific LLM techniques you employed (prompt engineering, fine-tuning), and the measurable outcomes?"

• "How do you approach gathering requirements from a client who may not fully understand the capabilities or limitations of conversational AI? Provide an example."

• "Walk me through your process for documenting a conversational flow in tools like Lucidchart or Voiceflow. What key elements do you ensure are included?"

Company & Culture Questions:

• "Why are you interested in Five9 and our work in conversational AI?"

• "How do you stay updated on the latest trends in AI and UX design?"

• "Describe a time you had to balance competing priorities or manage multiple customer projects simultaneously. How did you ensure successful delivery for all?"

Portfolio Presentation Strategy:

• Project Selection: Choose 2-3 projects that best showcase your LLM experience, documentation skills (Lucidchart/Voiceflow), and customer-facing achievements.

• Narrative Arc: Structure each presentation with a clear problem statement, your role and methodology, the design solution (highlighting AI/LLM components), challenges encountered, and quantifiable results.

• Tool Demonstration: Be ready to briefly show or discuss specific elements within your Lucidchart diagrams or Voiceflow prototypes to illustrate design detail and complexity.

• Quantify Impact: Focus on metrics – e.g., "Increased bot containment by X%", "Reduced average handling time by Y minutes," "Improved customer satisfaction scores by Z points."

• Future Vision: Discuss how you might further enhance or iterate on the presented solutions.

📝 Enhancement Note: Interview preparation should heavily focus on demonstrating practical application of LLMs, proficiency with specified design tools, and the ability to translate technical capabilities into client value and improved customer experiences.

📌 Application Steps

To apply for this Conversational UX Designer position:

• Submit your application through the Five9 careers portal via the provided link.

• Customize your resume and cover letter: Highlight specific experience with conversation design, LLMs, prompt engineering, fine-tuning, and customer-facing roles. Quantify achievements with relevant metrics and explicitly mention proficiency with tools like Lucidchart and Voiceflow.

• Prepare your portfolio: Curate 2-3 impactful case studies showcasing your best conversational AI designs, emphasizing LLM integration, detailed documentation (Lucidchart/Voiceflow examples), and demonstrable client success or operational efficiency gains. Ensure it's easily accessible (e.g., via a personal website or a shared document link).

• Research Five9: Understand their product offerings, market position in CCaaS, and any recent news or innovations related to AI. Familiarize yourself with their company values and culture, particularly the emphasis on customer obsession and innovation.

• Practice your presentation: Rehearse presenting your portfolio projects, focusing on clear articulation of your design process, technical contributions (especially with LLMs), and the business impact of your work.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.