Senior UX Designer

📍 Job Overview

Job Title: Senior UX Designer

Company: Cleo (US)

Location: Remote (United States)

Job Type: Full-Time

Category: UX Design / Product Design

Date Posted: May 22, 2026

Experience Level: 5-10 Years

Remote Status: Fully Remote

🚀 Role Summary

• Lead the design of AI-native enterprise experiences within complex supply chain environments, focusing on user-centric and business-outcome-driven solutions.

• Translate intricate supply chain challenges and AI capabilities into intuitive, elegant, and actionable user interfaces and workflows.

• Drive problem framing and user insight development by leveraging a blend of user research, data analytics, and AI-assisted discovery techniques.

• Collaborate deeply with Product Management, Engineering, Architecture, and Data/AI teams to define and deliver scalable, trustworthy, and high-impact user experiences.

• Champion the evolution of UX practices within an AI-centered product development lifecycle, influencing how intelligent capabilities are integrated and experienced by users.

📝 Enhancement Note: This role is positioned as a "Senior UX Designer" but the description emphasizes a strong focus on AI-native design, enterprise software, and complex supply chain workflows. This suggests the role requires not just traditional UX skills but also a strategic understanding of how AI can augment and transform user experiences in an operational context. The "AI-Native" aspect implies a forward-thinking approach to design, integrating AI not as an add-on but as a core component of the user journey.

📈 Primary Responsibilities

• Experience Strategy & Definition: Partner with Product Management and Architecture to define the overarching experience strategy for key platform areas, with a specific focus on how AI-driven capabilities are surfaced and integrated into user workflows.

• Problem Framing & User Insight: Lead the identification and framing of complex user problems within supply chain operations, utilizing user research, data analysis, and AI-assisted discovery to uncover high-impact opportunities for design intervention.

• End-to-End Design Execution: Translate ambiguity into clear experience direction through various fidelities, including rapid concepts, information architecture, wireframes, interactive prototypes, interaction models, detailed design specifications, and polished high-fidelity UI designs.

• AI-Centered Experience Design: Design user experiences that effectively leverage AI components such as recommendation systems, intelligent automation, conversational interfaces, predictive intelligence, decision-support workflows, and agentic interaction models.

• AI-Assisted Design Workflow Integration: Proactively utilize AI-assisted workflows throughout the UX process, including research synthesis, ideation, rapid prototyping, content generation, design exploration, usability analysis, and documentation to accelerate efficiency and innovation.

• Validation & Iteration: Drive continuous validation and learning by combining qualitative and quantitative research methods to rigorously evaluate experience effectiveness and inform iterative product decisions.

• Engineering Collaboration: Collaborate closely with engineering teams to ensure the high-quality implementation of designs, actively participating in real-time iteration, influencing technical trade-offs, and upholding a high standard for usefulness, usability, and polish.

• Cross-functional Advocacy: Act as a strong advocate for user and business outcomes within cross-functional decision-making processes, helping teams navigate complexity, ambiguity, and integrate AI effectively.

• Design System Evolution: Contribute to the development and scaling of design systems and interaction patterns that promote consistency while enabling innovation, particularly for AI-driven and data-rich experiences.

• Design Culture & Excellence: Foster a culture of design excellence and innovation, continuously raising the bar for craft, systems thinking, and the strategic role of UX within an AI-centered product development lifecycle.

📝 Enhancement Note: The responsibilities clearly indicate a senior-level role that goes beyond execution. The emphasis on "experience strategy," "problem framing," "AI-centered design," and "design system evolution" points to a strategic contributor who influences product direction and methodology. The integration of AI tools within the UX process itself is a key differentiator for this role.

🎓 Skills & Qualifications

Education:

Experience:

• 5+ years of experience designing complex, data-rich enterprise applications.

• Proven track record of simplifying challenging workflows into intuitive, high-impact user experiences.

• Experience leading UX for significant product areas or initiatives, influencing product direction across product, engineering, and design.

• Experience designing adaptive AI-infused experiences that combine intelligent guidance, automation, conversational workflows, and decision-support capabilities while preserving usability, explainability, user agency, and operational trust.

Required Skills:

• Enterprise UX Design: Proven ability to design complex, data-rich enterprise applications and simplify challenging operational workflows.

• AI-Infused Experience Design: Expertise in designing user experiences that integrate AI capabilities like recommendation systems, intelligent automation, and conversational interfaces.

• User Research & Insight Generation: Proficiency in conducting user research (qualitative and quantitative) and leveraging data to uncover user needs and opportunities.

• Systems Thinking: Strong ability to understand and design within complex technical domains, including data platforms and operational systems.

• Prototyping & Interaction Design: Skill in creating various fidelity prototypes, defining interaction models, and developing clear design specifications.

• Cross-functional Collaboration: Demonstrated ability to collaborate effectively with Product Management, Engineering, and Data/AI teams.

• Communication & Influence: Strong verbal and written communication skills, with the ability to articulate design rationale and align stakeholders.

• Problem Framing: Capability to navigate ambiguity and define clear experience direction for loosely defined problems.

• Design System Contribution: Experience contributing to or evolving design systems and interaction patterns for enterprise applications.

Preferred Skills:

• Supply Chain Domain Knowledge: Familiarity with supply chain logistics, operations, or related enterprise software domains.

• AI-Assisted Design Tools: Experience utilizing AI tools within the UX design process for research synthesis, ideation, or prototyping.

• Explainable AI (XAI) Design: Understanding of principles and best practices for designing AI systems that are transparent and understandable to users.

• Agentic Interaction Models: Experience designing for systems that can autonomously perform tasks or actions on behalf of the user.

• Usability Analysis: Deep understanding of evaluating experience effectiveness through various usability testing methodologies.

• Agile Development Environments: Experience working within iterative, agile product development lifecycles.

📝 Enhancement Note: The "AI-Native" requirement is a critical differentiator. Candidates should highlight any experience with AI/ML products, intelligent automation, conversational UIs, or systems that learn and adapt. The "5+ years" is a baseline, but the emphasis on complex enterprise applications and AI integration suggests that depth of experience in these specific areas will be heavily weighted.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• End-to-End Product Thinking: Demonstrate a comprehensive understanding of the product development lifecycle, from initial problem identification and user insight generation through to the successful launch and iteration of a product.

• Complex Workflow Simplification: Showcase case studies where you have taken a complex, data-rich enterprise workflow and transformed it into an intuitive, user-friendly, and high-impact experience.

• AI/Intelligent System Integration: Present examples of designs that effectively integrate AI capabilities, such as recommendation engines, intelligent automation, or predictive analytics, while maintaining user control and trust.

• Problem Framing & Solution Design: Clearly articulate the initial problem or opportunity, the user research and data that informed your approach, and the design solutions you developed, explaining the rationale behind key decisions.

• Collaboration & Iteration: Illustrate your ability to collaborate with cross-functional teams (Product, Engineering, Data/AI) and demonstrate how you incorporated feedback and iterated on designs based on technical constraints or user testing.

• Metrics & Outcomes: Where possible, include quantifiable results or key performance indicators (KPIs) that demonstrate the impact of your design solutions on user behavior, business objectives, or operational efficiency.

Process Documentation:

• Workflow Analysis & Design: Provide examples of how you have analyzed existing workflows, identified pain points, and designed optimized or automated processes using UX principles and AI-driven features.

• User Research Synthesis: Showcase your ability to synthesize qualitative and quantitative user research findings into actionable insights that drive design decisions, potentially using AI tools for synthesis.

• Design System Contributions: If applicable, demonstrate how you have contributed to or utilized design systems to ensure consistency and scalability, particularly for complex or AI-enhanced features.

• Usability Testing & Validation: Document your approach to user testing and validation, including how you gathered feedback and iterated on designs to improve usability and effectiveness.

📝 Enhancement Note: For this role, a portfolio is critical. It should not just showcase visual design but demonstrate a strategic approach to problem-solving, particularly in complex enterprise and AI-driven contexts. Candidates should be prepared to discuss their design process, including how they leveraged AI tools (if applicable) and how they ensured user trust and agency within AI-powered systems.

💵 Compensation & Benefits

Salary Range: $140,000 to $160,000 per year (plus bonus opportunity)

Benefits:

• Comprehensive Healthcare, Dental, and Vision insurance plans.

• Generous Flexible Paid Time Off (PTO) policy.

• 401k plan with company match.

• Flexible Spending Account (FSA) and Health Savings Account (HSA) options.

• Employee Assistance Program (EAP) for support services.

• Paid Parental Leave.

• Significant potential for accelerated title and salary growth.

• A culture that actively encourages work-life balance and provides a supportive environment.

Working Hours: The standard working hours are expected to align with a full-time role, likely around 40 hours per week. Given the remote nature and flexible PTO, there may be flexibility in daily scheduling, but consistent availability for core team meetings and collaboration will be expected.

📝 Enhancement Note: The salary range provided is specific and competitive for a Senior UX Designer role, especially in the US market for a fully remote position. The bonus opportunity indicates potential for additional compensation based on individual and company performance. The benefits package is robust and typical for competitive tech companies.

🎯 Team & Company Context

🏢 Company Culture

Industry: Enterprise Software (focus on Supply Chain and AI)

Company Size: The mention of "4,000+ clients" and implied growth suggests a well-established and growing company, likely in the mid-to-large enterprise software category.

Founded: Not specified, but the company's focus on AI and enterprise solutions indicates a modern, forward-thinking organization.

Team Structure:

• Cross-functional Product Teams: The Senior UX Designer will likely work within agile, cross-functional teams comprising Product Managers, Engineers (Frontend/Backend), Data Scientists/AI Specialists, and potentially other UX/Product Designers.

• Reporting Hierarchy: The role will likely report into a Head of Design, Design Manager, or Director of Product, with close collaboration across Product Management leadership.

• AI & UX Integration: A key cultural aspect will be the deep integration of AI and UX practices, fostering collaboration between design, engineering, and AI/data science teams to co-create intelligent user experiences.

Methodology:

• AI-First Product Development: The company embraces an AI-first approach, meaning AI is a core consideration from product conception to execution, influencing design and development processes.

• User-Centric Enterprise Design: A strong emphasis is placed on understanding complex enterprise user needs and translating them into intuitive, high-impact experiences, even within challenging domains like supply chain.

• Iterative & Data-Informed Design: The culture likely supports iterative design processes, informed by a combination of user research, product data, and AI-driven insights.

• Design Systems & Scalability: There's a focus on building scalable solutions, likely supported by robust design systems and consistent interaction patterns.

Company Website: meetcleo.com

📝 Enhancement Note: Cleo's positioning as an "AI-native" company in the enterprise software space suggests a culture that values innovation, cutting-edge technology, and solving complex business problems. The emphasis on AI and supply chain indicates a highly specialized and technical environment.

📈 Career & Growth Analysis

Operations Career Level: Senior Individual Contributor (IC) focused on strategic design leadership within product development. This role is positioned beyond a standard UX designer, requiring influence over product strategy and the integration of novel technologies like AI.

Reporting Structure: Will report to a design or product leadership role, with significant dotted-line collaboration across Product Management, Engineering, and Data/AI teams. This structure allows for both focused design work and broad influence.

Operations Impact: The Senior UX Designer will have a direct impact on the usability, adoption, and effectiveness of Cleo's enterprise software. By designing intuitive AI-infused experiences for complex supply chain workflows, they will contribute to improved decision-making, increased operational efficiency, and enhanced customer retention (given the company's 99% retention rate). Their work will shape how businesses leverage AI in their day-to-day operations.

Growth Opportunities:

• Leadership in AI UX: Opportunity to become a recognized expert in designing AI-native enterprise experiences, a highly sought-after skill set.

• Strategic Influence: Grow influence over product strategy and the direction of Cleo's AI product roadmap.

• Mentorship: Potential to mentor junior designers and contribute to the growth of the design team.

• Advanced Skill Development: Deepen expertise in areas like conversational AI design, agentic systems, explainable AI, and advanced data visualization within enterprise contexts.

• Accelerated Title/Salary Growth: The company explicitly mentions "accelerated title and salary growth potential," suggesting a meritocratic environment that rewards high performance and impact.

📝 Enhancement Note: The "accelerated title and salary growth potential" is a significant draw for senior-level talent. Candidates should focus on demonstrating strategic thinking and leadership potential beyond just design execution to align with this growth trajectory.

🌐 Work Environment

Office Type: Fully Remote. This implies a distributed team environment where asynchronous communication and strong digital collaboration tools are paramount.

Office Location(s): United States. While remote, the company operates within the US market, and timezone alignment (e.g., America/Chicago mentioned but likely flexible for US-based candidates) may be a consideration for team syncs.

Workspace Context:

• Digital Collaboration: Expect a heavy reliance on collaboration tools (e.g., Slack, Zoom, Miro, Figma) for communication, ideation, and design reviews.

• AI Integration in Workflows: The workspace will likely incorporate AI tools not just in the product being designed but also in the design process itself, requiring adaptability and a willingness to experiment.

• Cross-functional Interaction: Opportunities for deep interaction with diverse teams (Product, Engineering, Data/AI), fostering a learning environment and exposure to different technical domains.

• Focus on Autonomy: Remote work requires a high degree of self-discipline, time management, and proactive communication.

Work Schedule: While the core work is full-time (approx. 40 hours/week), the remote nature and flexible PTO suggest a degree of autonomy in scheduling. However, availability for critical meetings, design critiques, and cross-functional syncs during core business hours (likely aligned with US time zones) will be essential for effective collaboration.

📝 Enhancement Note: For a remote role, candidates should highlight their experience with remote collaboration tools, asynchronous communication strategies, and their ability to manage their workload independently while remaining connected to the team.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A brief call with a recruiter to assess overall fit, experience alignment, and salary expectations.

• Portfolio Review & Design Discussion: A deeper dive with design leadership or senior designers to present your portfolio, discuss your process, and explore key case studies. This is where your ability to articulate complex design decisions and your experience with enterprise/AI design will be evaluated.

• Cross-functional Interviews: Interviews with Product Management and Engineering stakeholders to assess collaboration skills, understanding of technical constraints, and ability to integrate AI effectively into product solutions.

• Design Challenge/Workshop: Potentially a take-home assignment or a live design workshop focused on a relevant problem, assessing your problem-solving approach, design thinking, and ability to work under pressure.

• Final Round: Discussion with senior leadership to assess strategic thinking, cultural fit, and overall potential for growth within the company.

Portfolio Review Tips:

• Curate Strategically: Select 2-3 of your strongest projects that best showcase your experience with complex enterprise applications, AI-infused designs, and end-to-end product thinking.

• Tell a Story: For each project, clearly articulate the problem, your role, the process you followed (emphasizing research, ideation, and iteration), your design decisions, and the outcomes.

• Highlight AI Integration: If you have experience with AI/ML products, explicitly detail how you designed for these features, focusing on user trust, explainability, and agency. If not, discuss your strategic thinking around how AI could be integrated.

• Quantify Impact: Whenever possible, use metrics and data to demonstrate the impact of your designs on user behavior, business goals, or operational efficiency.

• Be Prepared for Process Questions: Expect to be asked about your design process, how you handle ambiguity, how you collaborate with engineers, and how you approach user research.

• Showcase Systems Thinking: Demonstrate your ability to design within complex systems and contribute to scalable design solutions.

Challenge Preparation:

• Understand the Domain: Familiarize yourself with Cleo's products, the supply chain industry, and the challenges of AI integration in enterprise software.

• Practice Problem Framing: Be ready to dissect a vague problem statement, ask clarifying questions, and define clear objectives for a design challenge.

• Outline Your Process: For any design challenge, have a structured approach ready: understand, explore, define, ideate, prototype, test, iterate.

• Focus on AI & Enterprise Context: Tailor your approach to the specific context of complex enterprise workflows and the potential of AI.

• Articulate Trade-offs: Be prepared to discuss design trade-offs (e.g., usability vs. functionality, AI capabilities vs. user control) and justify your decisions.

📝 Enhancement Note: The mention of "AI-Native" and "Supply Chain" in the job description means interviewers will be looking for candidates who can speak intelligently about these domains and demonstrate how UX principles apply. Candidates should research Cleo's offerings and the challenges within enterprise supply chain management.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (highly probable for modern design teams), Sketch, Adobe Creative Suite (Illustrator, Photoshop).

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

• Whiteboarding & Ideation: Miro, Mural.

• User Research Platforms: UserTesting.com, Lookback, Maze, or similar tools for remote usability testing.

• Design System Management: Tools integrated within Figma or separate platforms for managing design tokens and components.

Analytics & Reporting:

• Product Analytics: Mixpanel, Amplitude, Google Analytics, or similar platforms for understanding user behavior within the application.

• Data Visualization: Tableau, Power BI, or internal dashboards for analyzing user data and reporting on design impact.

CRM & Automation (for understanding user/customer context):

• While not directly a UX tool, familiarity with CRM systems (e.g., Salesforce) or customer success platforms can provide valuable context for enterprise software design.

📝 Enhancement Note: Proficiency in modern UX tools, especially Figma, is almost a given for this type of role. The ability to work with and potentially contribute to design systems is also crucial. Familiarity with AI-assisted design tools, even if experimental, would be a strong plus.

👥 Team Culture & Values

Operations Values:

• Innovation & AI-First: A strong drive to push boundaries with AI and technology to solve complex problems, valuing forward-thinking solutions.

• User-Centricity: Deep commitment to understanding and serving the needs of enterprise users, even in challenging operational environments.

• Impact & Outcomes: Focus on delivering tangible business value and operational improvements through thoughtful design.

• Collaboration & Transparency: Open communication and close partnership across product, engineering, and data/AI teams are essential.

• Excellence & Craft: A high standard for the quality, usability, and polish of the final product experience.

• Learning & Adaptability: A culture that encourages continuous learning, especially in rapidly evolving fields like AI and enterprise UX.

Collaboration Style:

• Cross-functional Partnership: Expect extensive collaboration with Product Management for strategy and requirements, Engineering for implementation feasibility and trade-offs, and Data/AI teams for understanding and leveraging intelligent capabilities.

• Iterative Design Critiques: Regular design reviews and feedback sessions with peers and leadership to refine solutions.

• Data-Informed Decision Making: A culture that values data and user research as key inputs to design decisions, fostering evidence-based discussions.

• Proactive Communication: In a remote, AI-integrated environment, proactive and clear communication is vital for keeping all stakeholders aligned.

📝 Enhancement Note: The "AI-Native" and "enterprise software" context suggests a culture that balances cutting-edge technology with practical, business-focused solutions. Candidates should demonstrate an ability to be both innovative and pragmatic.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Ambiguity: Navigating loosely defined problems and translating complex, evolving AI capabilities into clear, intuitive user experiences.

• Balancing AI Power with User Control: Ensuring AI-driven features enhance productivity without overwhelming users, compromising agency, or eroding trust. This includes designing for explainability and graceful failure modes.

• Integrating AI into Existing Workflows: Seamlessly embedding AI capabilities into established, complex operational workflows without causing disruption.

• Keeping Pace with AI Advancements: Continuously learning about new AI technologies and methodologies and applying them effectively to design challenges.

• Remote Collaboration & Communication: Maintaining strong team cohesion and effective communication in a fully remote, distributed environment.

• Quantifying Design Impact: Demonstrating the ROI and business impact of UX design, especially in the context of AI-driven features.

Learning & Development Opportunities:

• Specialization in AI UX: Opportunity to become a leading expert in designing for AI-native enterprise applications, a rapidly growing and high-demand field.

• Exposure to Cutting-Edge AI: Work directly with advanced AI technologies and data science teams, gaining deep insights into their application.

• Strategic Product Influence: Grow from an execution-focused role to one that significantly influences product strategy and roadmap.

• Mentorship and Leadership: Potential to mentor junior designers, lead design initiatives, and grow into leadership positions within the design team.

• Industry Conferences & Training: Support for attending relevant design and AI conferences, workshops, and pursuing certifications.

📝 Enhancement Note: The challenges highlight the complex and evolving nature of AI UX design in an enterprise context. Candidates who thrive in ambiguity and are passionate about learning will be well-suited.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to design for a complex, data-rich enterprise workflow. What was the problem, and how did you simplify it?" (Focus on process, user research, and outcome)

• "How would you approach designing an AI-driven recommendation system for supply chain logistics? What are the key considerations for user trust and adoption?" (Assess strategic thinking, AI understanding, and user-centricity)

• "Imagine you're given a vague requirement for an 'intelligent automation' feature. How would you begin to frame the problem, conduct research, and define the user experience?" (Tests problem framing, ambiguity handling, and research methodology)

• "Discuss your experience designing conversational interfaces or agentic systems. What are the unique challenges and opportunities?" (Evaluates specific AI UX experience)

Company & Culture Questions:

• "What interests you about Cleo's AI-native approach to enterprise software, specifically in the supply chain domain?" (Shows research and genuine interest)

• "How do you see AI transforming the role of UX design in the future?" (Gauges forward-thinking and industry awareness)

• "Describe your ideal remote work environment and how you ensure effective collaboration with a distributed team." (Assesses remote work readiness and communication skills)

• "How do you stay updated on the latest trends in AI and UX design?" (Highlights commitment to learning)

Portfolio Presentation Strategy:

• Structure for Impact: Start with the most compelling project. For each, clearly state the problem, your role, and the high-level outcome.

• Walk Through Your Process: Detail your research methods, ideation techniques, and iteration cycles. Explain why you made certain design decisions.

• Showcase AI/Complex Solutions: Emphasize how you tackled complexity and integrated AI elements, focusing on user benefits and design rationale.

• Highlight Collaboration: Mention how you worked with cross-functional teams and incorporated their feedback.

• Quantify Results: Use metrics to demonstrate the success of your designs. If metrics aren't available, discuss the intended impact and how you would measure it.

• Be Prepared for Deep Dives: Anticipate detailed questions about specific design choices, user research findings, and technical considerations.

📝 Enhancement Note: Interview preparation should heavily focus on demonstrating strategic thinking, a deep understanding of AI's role in UX, and the ability to navigate complex enterprise environments. Candidates should be ready to discuss their process for handling ambiguity and balancing innovation with user needs and operational realities.

📌 Application Steps

To apply for this operations position:

• Submit your application through the provided Greenhouse link.

• Portfolio Customization: Ensure your resume and portfolio are tailored to highlight your experience in complex enterprise applications, AI-infused design, and supply chain workflows. Prioritize case studies that demonstrate end-to-end product thinking and successful simplification of challenging operational processes.

• Resume Optimization: Clearly articulate your years of experience, specific contributions to AI-driven features, and your ability to collaborate cross-functionally. Use keywords from the job description such as "AI-Native," "Enterprise UX," "Supply Chain," "User Research," and "Systems Thinking."

• Interview Preparation: Practice articulating your design process, especially how you handle ambiguity and integrate AI. Prepare to discuss your portfolio projects in detail, focusing on the "why" behind your design decisions and the impact of your work. Be ready to discuss your thoughts on AI's role in UX.

• Company Research: Thoroughly research Cleo, its products, and its positioning in the market. Understand their AI-native strategy and the challenges within the supply chain industry to better frame your answers and demonstrate genuine interest.

⚠️ 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.