(Senior) UX/UI Product Designer

📍 Job Overview

Job Title: Senior UX/UI Product Designer

Company: Leopard (Coventry)

Location: Fort Washington, Pennsylvania, United States

Job Type: Full-Time

Category: Product Design / User Experience Operations

Date Posted: 2026-06-08

Experience Level: 5-10 Years (Senior Level)

Remote Status: Hybrid (2 days in-office per week)

🚀 Role Summary

• Drive the end-to-end design of core user journeys across both internal business operations tools and external consumer-facing product interfaces.

• Define and evolve the product surfaces' information architecture and ontology, ensuring intuitive navigation and efficient operation for diverse user groups.

• Establish the design foundation for AI-powered features, integrating intelligent guidance, dynamic recommendations, and agent-driven workflows.

• Build and maintain a scalable design system to ensure consistency, accessibility, and readiness for future product expansion.

• Contribute significantly to the product roadmap through user insights and design thinking, shaping the future trajectory of company workflows and external customer experiences.

📝 Enhancement Note: While the title is "(Senior) UX/UI Product Designer," the description and experience requirements (3-7 years with a strong portfolio, and the mention of being the first staff designer with wide scope and real influence) strongly indicate a Senior level designation. The role spans both B2B (internal business operations) and B2C (external consumer) product design, requiring a comprehensive understanding of different user needs and operational workflows. The emphasis on AI-native platforms and generative AI tools positions this as a forward-looking role within the insurtech and life settlement market.

📈 Primary Responsibilities

• Own the complete design lifecycle for key user journeys, translating complex employee tooling use-cases and external customer interfaces into intuitive wireframes, mockups, and interactive prototypes.

• Develop and refine the information architecture and ontology for product surfaces, ensuring clear categorization and conceptual models that facilitate rapid navigation and effective operation for both expert and novice users.

• Design user experiences for AI-powered functionalities, focusing on seamless integration of intelligent guidance, personalized recommendations, and efficient agent-driven workflows.

• Create, implement, and maintain a robust design system to ensure a consistent, accessible, and scalable user experience across all product touchpoints.

• Collaborate closely with product management and engineering teams to contribute user insights and design thinking to the product roadmap, influencing strategic decisions and future product direction.

• Advocate for and educate stakeholders on design best practices, fostering a strong design culture within the organization.

• Conduct user research to gather insights, validate design decisions, and inform product strategy.

• Design for high-stakes decision-making environments, ensuring clarity, trust, and ease of use in complex financial and insurance contexts.

📝 Enhancement Note: The responsibilities clearly indicate a need for a designer who can operate independently, manage projects from conception to completion, and influence product strategy. The emphasis on information architecture and ontology suggests a need for a designer with a strong understanding of complex data structures and how users interact with them, especially in regulated industries. The integration of AI tools necessitates a forward-thinking approach to UX/UI design.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a Bachelor's or Master's degree in Design, Human-Computer Interaction, Computer Science, or a related field, or equivalent practical experience, is highly beneficial for understanding design principles and user psychology.

Experience: 3–7 years of professional product design experience, with a proven track record of shipping successful B2B and B2C products. Experience in early-stage startups and regulated industries like life insurance, fintech, or healthtech is a significant advantage.

Required Skills:

• UX Design Fundamentals: Deep understanding of information architecture, interaction design, user flows, user research methodologies, and usability principles.

• UI Craftsmanship: Exceptional visual design skills, including typography, visual hierarchy, layout, spacing, and the ability to create production-ready designs.

• Prototyping & Wireframing: Proficiency in creating detailed wireframes, mockups, and interactive prototypes to effectively communicate design concepts and user flows.

• Design Systems: Experience in building, maintaining, and scaling design systems for consistency and efficiency.

• Figma Proficiency: Advanced skills in Figma for design, prototyping, and collaboration.

• AI & Generative AI Integration: Demonstrated experience and a strong point of view on actively using AI and generative AI tools in the design workflow to enhance speed, creativity, and outcomes.

• Communication & Collaboration: Excellent verbal and written communication skills, with the ability to present and defend design decisions, receive feedback constructively, and work effectively in a fast-paced, collaborative environment.

• Project Ownership: Proven ability to own projects end-to-end, manage timelines, and deliver against project milestones.

• High-Stakes Design: Experience designing for users making critical, high-stakes decisions.

Preferred Skills:

• Experience in life insurance, fintech, healthtech, or other high-trust consumer product sectors.

• Background in content design, UX writing, or applying plain language standards in regulated industries.

• Familiarity with conversion optimization, funnel analysis, or designing with quantitative user data.

• Experience in early-stage startup environments.

📝 Enhancement Note: The 3-7 year experience range is typical for a Senior Product Designer. The emphasis on AI tools suggests the company is looking for someone who is not just familiar but actively integrating these technologies. The "Extra points" section highlights specialized knowledge that would be highly valued, particularly in the context of the company's industry.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A comprehensive portfolio showcasing shipped B2B and B2C products, demonstrating a full range of design skills.

• Detailed case studies that highlight user research findings, information architecture decisions, interaction design rationale, wireframes, mockups, and the final live product.

• Examples of how you have designed for complex user journeys and high-stakes decision-making scenarios.

• Evidence of your ability to define and evolve information architecture and ontologies.

• Demonstrations of your experience with AI and generative AI tools integrated into your design process and their impact on outcomes. Process Documentation:

• Showcase your process for conducting user research, from planning to synthesis and application of insights.

• Illustrate your approach to information architecture design, including methods for organizing complex content and user flows.

• Provide examples of your workflow for creating wireframes, mockups, and interactive prototypes, detailing the tools and techniques used.

• Document your experience in building or contributing to design systems, including its components, guidelines, and impact on efficiency.

• Case studies should clearly outline the problem, your process, your role, the solutions you designed, and the measurable impact or results achieved.

📝 Enhancement Note: For a Senior UX/UI Product Designer, the portfolio is paramount. It needs to go beyond just aesthetics and demonstrate strategic thinking, problem-solving skills, a deep understanding of user-centered design principles, and the ability to translate complex business needs into intuitive user experiences. For this role, showcasing experience with AI tools and their practical application in a design workflow is crucial.

💵 Compensation & Benefits

Salary Range: USD $130,000.00 to $160,000.00 per year. The exact salary and the "Senior" designation will be determined based on the candidate's experience, location, and performance.

Benefits:

• Health Insurance

• 401(k) retirement plan

• Free in-office food and drinks

• Paid Holidays

• Encouraged Paid Time Off (PTO)

• Eligibility for short-term incentives

• Eligibility for long-term incentives

• Equity participation

Working Hours: The role is full-time, with an anticipated 40 hours per week. The hybrid work model requires being in the office two days a week, with flexibility on which days those are, allowing for concentrated work at home or in the office.

📝 Enhancement Note: The salary range provided is within the typical band for a Senior UX/UI Product Designer in a high-cost-of-living area like the New York metropolitan vicinity (proximity to Madison Square Garden), especially for specialized roles in tech and finance. The "Senior" aspect of the title is explicitly tied to experience and performance, suggesting a clear path for advancement and recognition. The inclusion of incentives and equity points to a performance-driven compensation structure common in growth-stage tech companies.

🎯 Team & Company Context

🏢 Company Culture

Industry: The company operates in the Life Insurance and Annuity sector, specifically focusing on life settlements and modernizing transactions through technology. This is a high-trust industry requiring meticulous design for complex financial decisions. The company is also heavily invested in an AI-native platform and insurtech.

Company Size: Part of Coventry, a market leader founded in 1982, which acquired Leopard (an insurtech incubated by The D. E. Shaw Group's venture studio) in 2025. This suggests a blend of established market presence with a dynamic, startup-like technological innovation arm. The team structure for this specific role is likely small and focused, as the designer is the first staff designer.

Founded: Coventry was founded in 1982. Leopard was launched in 2024. This indicates a company with deep market history now rapidly integrating cutting-edge technology.

Team Structure:

• This role reports to the VP of Product, indicating a senior-level position with direct access to leadership.

• The designer will be the "first staff designer," implying a foundational role with significant influence and the potential to build out a design team.

• Close collaboration with product managers and engineers is expected, typical of product development teams.

• The company is fostering a "product-driven tech culture" with a focus on AI. Methodology:

• Data-Driven Design: Emphasis on using user insights, quantitative data, and conversion optimization to inform design decisions.

• AI Integration: Actively leveraging AI and generative AI tools in the design workflow and for product features.

• Agile Development: Implied by the fast-paced, collaborative environment and the need to contribute to roadmaps and iterate quickly.

• Design Thinking: Expected to apply design thinking principles to solve complex problems and contribute to product strategy.

Company Website: Coventry: https://www.coventry.com/ (Note: The provided URL in the input is for Workable, the job board, not the company website itself.)

📝 Enhancement Note: The company's focus on modernizing complex financial transactions via an AI-native platform is a key differentiator. This role offers a unique opportunity to shape the design direction of a category leader undergoing significant technological transformation. The blend of established market presence with a startup mentality for its tech arm creates an exciting dynamic.

📈 Career & Growth Analysis

Operations Career Level: Senior Product Designer. This level implies a high degree of autonomy, strategic contribution, and ownership of significant product areas. The role is positioned to influence the company's technological direction and design culture.

Reporting Structure: Reports directly to the VP of Product. This provides visibility and direct access to senior leadership, facilitating faster decision-making and greater impact.

Operations Impact: The designer will have a direct impact on how both internal business operations and external customers interact with critical financial products. By designing intuitive interfaces for complex processes like life insurance and annuities, the role will influence customer satisfaction, operational efficiency, and the adoption of new AI-powered features. The work directly supports Coventry's ambition to modernize these transactions at scale.

Growth Opportunities:

• Team Leadership: As the first staff designer, there is a clear opportunity to grow into a leadership role, building and managing a design team as the company scales its product efforts.

• Specialization: Deepen expertise in designing for regulated industries, high-stakes financial decisions, and cutting-edge AI/LLM applications within product design.

• Strategic Influence: Contribute directly to product strategy and roadmap development, shaping the future direction of the company's AI-native platform.

• Industry Expertise: Develop specialized knowledge in the life settlement, life insurance, and annuity markets, becoming a subject matter expert.

• Mentorship: Opportunity to mentor junior designers as the team grows.

📝 Enhancement Note: This role offers a rare opportunity for a designer to be a foundational member of a product team, with significant potential for leadership growth and strategic impact. The dual focus on internal operations and external customer experience provides a broad scope for skill development.

🌐 Work Environment

Office Type: Hybrid model with 2 days per week in-office. The office is located near Madison Square Garden in New York, NY. This suggests a vibrant, urban work environment.

Office Location(s): The primary office is in New York, NY. Coventry's headquarters are in Fort Washington, PA, implying potential for occasional travel or collaboration with the HQ team.

Workspace Context:

• Collaborative Environment: The role emphasizes close collaboration with product and engineering teams, suggesting an open and interactive workspace designed to foster teamwork.

• Tools & Technology: Access to modern design tools, particularly Figma, and the expectation to actively use AI and generative AI tools, indicates a tech-forward environment.

• Team Interaction: As the first staff designer, there will be significant interaction with product leadership and engineering, creating opportunities to influence processes and discussions.

• Amenities: The office provides free in-office food and drinks, contributing to a comfortable and productive work atmosphere.

Work Schedule: Full-time (approx. 40 hours/week) with a hybrid arrangement. The flexibility to choose in-office days allows for better work-life integration, balancing focused individual work with collaborative team sessions.

📝 Enhancement Note: The hybrid model, combined with the office location in a major hub like New York City, offers a balance of flexibility and in-person collaboration. The emphasis on AI tools suggests a willingness to invest in cutting-edge technology within the workspace.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Likely a review of your resume and portfolio to assess qualifications and alignment with the role's requirements, particularly experience with Figma, AI tools, and B2B/B2C products.

• Portfolio Presentation & Discussion: Expect to present your portfolio, walking through case studies that demonstrate your design process, problem-solving skills, and impact. Be prepared to discuss your experience with information architecture, AI integration, and designing for complex user journeys.

• Design Challenge: A practical exercise may be given, either take-home or during an interview, to assess your design thinking, problem-solving abilities, and proficiency with design tools. This could involve a specific scenario related to their industry or platform.

• Cross-Functional Interviews: Interviews with Product Managers and Engineers to assess collaboration style, communication skills, and ability to integrate into the existing team.

• Leadership Interview: Meeting with the VP of Product to discuss strategic thinking, leadership potential, cultural fit, and career aspirations.

Portfolio Review Tips:

• Curate Strategically: Select 3-5 of your strongest projects that best showcase your experience with B2B, B2C, AI integration, information architecture, and high-stakes decision design.

• Tell a Story: For each case study, clearly articulate the problem, your role, your design process (research, ideation, prototyping, testing), the solutions you developed, and the measurable outcomes or impact.

• Highlight AI Usage: Specifically detail how you leveraged AI and generative AI tools, explaining the benefits and any unique insights or efficiencies gained.

• Showcase Process: Emphasize your thought process, decision-making rationale, and how you adapted to challenges.

• Be Ready for Deep Dives: Prepare to discuss the technical aspects of your designs, your understanding of information architecture, and your approach to creating scalable design systems.

• Demonstrate Communication: Practice presenting your work clearly, concisely, and engagingly. Be ready to answer detailed questions about your contributions.

Challenge Preparation:

• Understand the Industry: Research life insurance, annuities, life settlements, and the insurtech landscape. Familiarize yourself with common user pain points and regulatory considerations.

• Practice AI Integration: Think about how you would use AI tools to solve design problems in this domain, from ideation to content generation to UX flow optimization.

• Focus on IA/Ontology: Be prepared for challenges that might involve organizing complex information or defining user taxonomies.

• Structure Your Approach: For any design challenge, outline your problem-solving framework, research approach, ideation techniques, and how you would validate your solution.

📝 Enhancement Note: The interview process will likely be rigorous, focusing heavily on portfolio and practical design skills. The emphasis on AI and the specific industry means candidates should tailor their preparation to showcase relevant experience and a forward-thinking mindset.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The core tool for UI design, prototyping, and collaboration. Proficiency is essential.

• Generative AI Tools: Actively using AI and generative AI tools (e.g., Midjourney, Stable Diffusion, LLM-based assistants for ideation or content) in the design workflow. Candidates should have a strong point of view on their application.

• Prototyping Tools: Beyond Figma, familiarity with other prototyping tools for specific needs may be beneficial.

Analytics & Reporting:

• While not explicitly listed as a requirement for the designer, understanding how to interpret data from analytics platforms (e.g., Google Analytics, Amplitude, Mixpanel) and using it to inform design decisions is a strong asset.

• Experience with A/B testing and conversion optimization tools and methodologies would be highly valued. CRM & Automation:

• Understanding of CRM systems (like Salesforce) and automation platforms is beneficial, especially for designing internal business operations tools. The ability to design workflows that integrate with or automate processes within these systems is a plus.

• Familiarity with the broader insurtech ecosystem and related platforms.

📝 Enhancement Note: The explicit mention of "AI-native platform" and "generative AI tools" is a critical indicator of the technology stack. Candidates must demonstrate not just awareness but practical, hands-on experience and a strategic perspective on using these technologies in a design context.

👥 Team Culture & Values

Operations Values:

• Curiosity: A drive to ask questions, explore new technologies (especially AI), and understand complex problems deeply.

• Craftsmanship: High standards for design quality, attention to detail, and a commitment to creating polished, user-friendly experiences.

• Ownership: Taking responsibility for projects end-to-end, from concept to launch and iteration, with a proactive approach.

• Collaboration: Working effectively with product, engineering, and other stakeholders, valuing diverse perspectives and open communication.

• Data-Informed Decisions: Utilizing user research and quantitative data to guide design choices and measure impact.

• Adaptability: Flexibility to evolve design processes as new tools and methodologies become available, particularly with the rapid advancements in AI.

Collaboration Style:

• Cross-functional Integration: Working closely with product managers to define requirements and strategy, and with engineers to ensure feasible and high-quality implementation.

• Feedback Culture: Openness to receiving and giving constructive feedback to improve designs and processes.

• Transparent Communication: Regularly sharing design progress, rationale, and challenges with relevant teams and leadership.

• Proactive Engagement: Actively participating in team discussions, contributing ideas, and helping to define best practices, especially in the nascent area of AI in design.

📝 Enhancement Note: The company is clearly building a culture that embraces innovation, particularly around AI, and values designers who are not just executors but strategic thinkers who take ownership and collaborate effectively. The emphasis on "craft" and "curiosity" suggests a team that values both technical skill and a passion for learning and improvement.

⚡ Challenges & Growth Opportunities

Challenges:

• Pioneering AI in Design: Being at the forefront of integrating AI and generative AI into design workflows and product features for a complex industry. This requires continuous learning and experimentation.

• Designing for High-Stakes Decisions: Creating intuitive and trustworthy user experiences for financial and insurance products where user errors can have significant consequences.

• Balancing B2B and B2C Needs: Designing for both internal operational efficiency and external customer engagement, often requiring different approaches and user considerations within a unified platform.

• Establishing Design Foundation: As the first staff designer, the challenge is to build and scale the design practice, establish processes, and potentially grow a team from the ground up.

• Educating Stakeholders: Guiding non-designers on the value and application of design thinking and best practices, particularly concerning new technologies like AI.

Learning & Development Opportunities:

• AI/LLM Specialization: Deepen expertise in applying AI and LLMs to product design, becoming a leader in this emerging field within the insurtech/fintech space.

• Leadership Development: Opportunity to build and manage a design team, developing mentorship and people management skills.

• Industry Expertise: Gain in-depth knowledge of the life insurance, annuities, and life settlement markets, becoming a subject matter expert.

• Strategic Product Influence: Contribute significantly to the product strategy and roadmap, impacting the company's direction and innovation.

• Continuous Skill Enhancement: Access to resources, potentially industry conferences, and a culture that encourages exploration of new design tools and methodologies.

📝 Enhancement Note: This role presents significant challenges that are also rich opportunities for growth. The company is looking for someone who thrives in ambiguity and is eager to shape the future of design within their organization and industry.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you designed a complex user journey for both internal business operations and external customers. What were the key differences in your approach, and how did you ensure consistency?"

• "How have you integrated AI or generative AI tools into your design process? Can you walk us through a specific example and its impact on the outcome?"

• "Tell us about a challenging design problem you faced in a regulated industry (like finance or healthtech). How did you approach it, and what was the resolution?"

• "How do you approach defining and evolving the information architecture and ontology for a product? Can you share an example where this was critical?" Company & Culture Questions:

• "What excites you most about Coventry's mission and its use of an AI-native platform?"

• "How do you see yourself contributing to building a design culture at Leopard, especially as the first staff designer?"

• "Describe your experience working in a fast-paced, collaborative environment. How do you handle feedback and disagreements with product or engineering teams?"

• "What are your thoughts on the balance between structured design processes and the need for agility, especially with emerging technologies like AI?" Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly define the problem, your role, your process (research, ideation, prototyping, testing), the solution, and the impact. Use visuals effectively.

• Emphasize AI Integration: Dedicate specific slides or talking points to detail your use of AI/generative AI tools, explaining why and how they were used, and the tangible benefits.

• Highlight IA/Ontology: Be prepared to deep-dive into your information architecture decisions, explaining the rationale behind your categorization and labeling strategies.

• Showcase Impact: Quantify results whenever possible (e.g., improved conversion rates, reduced task completion time, increased user satisfaction). If exact metrics aren't available, articulate the expected business impact.

• Be Ready for Technical Questions: Anticipate questions about your Figma skills, design system development, and your understanding of how designs get implemented by engineers.

• Ask Insightful Questions: Prepare thoughtful questions about the team, product roadmap, challenges, and company culture to demonstrate your engagement and strategic thinking.

📝 Enhancement Note: Interview preparation should focus on demonstrating strategic thinking, practical application of design skills (especially with AI and IA), and strong communication abilities. The company values individuals who are proactive, curious, and can drive impact in a dynamic environment.

📌 Application Steps

To apply for this Senior UX/UI Product Designer position:

• Submit your application through the provided link on Workable.

• Customize Your Resume: Tailor your resume to highlight experience in B2B/B2C product design, AI/generative AI tools, information architecture, and working in regulated industries. Use keywords from the job description.

• Curate Your Portfolio: Select your strongest projects that align with the requirements, focusing on detailed case studies that showcase your process, problem-solving, and impact, especially with AI integration.

• Prepare Your Presentation: Practice walking through your portfolio case studies, articulating your design decisions, rationale, and the outcomes clearly and concisely. Be ready to discuss your experience with Figma and AI tools in detail.

• Research Leopard & Coventry: Understand their mission, market, and commitment to an AI-native platform. Prepare thoughtful questions about their product strategy and design culture.

⚠️ 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.