Senior UX/UI Product Designer

📍 Job Overview

Job Title: Senior UX/UI Product Designer

Company: Leopard (part of Coventry)

Location: Fort Washington, Pennsylvania, United States

Job Type: FULL_TIME

Category: Product Design / UX/UI

Date Posted: 2026-08-06

Experience Level: 5-10 Years

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

🚀 Role Summary

• Lead the end-to-end design of complex user journeys for both internal business operations tools and external consumer-facing platforms.

• Shape the user experience for AI-powered features, focusing on intuitive interaction with intelligent guidance and dynamic recommendations.

• Develop and maintain a robust design system to ensure consistency, accessibility, and scalability across all product surfaces.

• Drive product strategy through user insight and design thinking, influencing the future trajectory of insurance and annuity transactions.

• Collaborate closely with product and engineering teams to translate complex financial processes into user-friendly interfaces.

📝 Enhancement Note: This role is positioned as the "first staff designer," implying significant ownership, influence, and potential for future team leadership. The focus on both internal business operations tools and external consumer interfaces, combined with AI integration and regulated industry context, suggests a highly strategic and impactful design position. The hybrid model with specific in-office days indicates a structured approach to collaboration and team integration.

📈 Primary Responsibilities

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

• Define and continuously evolve the information architecture and ontology of product surfaces, establishing clear labels, categories, and conceptual models for efficient navigation by both expert and novice users.

• Architect the user experience for emerging AI-powered functionalities, ensuring seamless integration of intelligent guidance, personalized recommendations, and agent-driven workflows for consumers and internal business users.

• Create, manage, and iterate on a comprehensive design system to ensure a consistent, accessible, and scalable user experience across all digital touchpoints.

• Contribute substantively to the product roadmap by providing deep user insights and applying design thinking methodologies, thereby shaping the strategic direction of Coventry's operational workflows and external interfaces.

• Educate and evangelize design best practices to stakeholders across product, engineering, and business units to foster a strong design-centric culture.

• Collaborate with cross-functional teams to conduct user research, gather feedback, and iterate on designs based on quantitative and qualitative data.

📝 Enhancement Note: The responsibilities highlight a blend of strategic product definition, hands-on design execution, and cross-functional influence. The emphasis on "owning end-to-end design" and "establishing the design foundation for AI-powered features" points to a senior-level individual contributor role with substantial autonomy. The requirement to "define and evolve the product surfaces' information architecture and ontology" suggests a need for deep analytical and organizational design skills.

🎓 Skills & Qualifications

Education: Bachelor's degree in Design, Human-Computer Interaction, Computer Science, or a related field, or equivalent practical experience.

Experience: 3–7 years of professional product design experience, with a proven track record of shipping B2B and B2C-facing products.

Required Skills:

• Demonstrated expertise in UX fundamentals, including information architecture, interaction design, user flows, and designing for users navigating high-stakes decisions.

• Strong UI craft and proficiency in Figma, with a keen eye for typography, visual hierarchy, spacing, and creating production-ready design assets.

• Active and proficient use of AI and generative AI tools within the design workflow, with a nuanced understanding of their impact beyond mere speed improvements.

• Exceptional communication skills, with the ability to clearly articulate and defend design decisions, receive and integrate feedback constructively, and thrive in a fast-paced, collaborative environment.

• Proven ability to own projects from inception to completion, consistently delivering against project milestones and business objectives.

• A strong portfolio showcasing shipped B2B and B2C products, detailing user research, ontological decisions, wireframes, and live product examples. Preferred Skills:

• Experience within the life insurance, fintech, or healthtech industries, or in any high-trust consumer product sector where anxiety and decision complexity are primary design challenges.

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

• Prior experience working in an early-stage startup environment, demonstrating adaptability and a proactive approach.

• Familiarity with conversion optimization techniques, funnel analysis, and the principles of designing with quantitative user data.

📝 Enhancement Note: The experience requirement (3-7 years) aligns with a senior individual contributor role, while the "first staff designer" designation implies a need for leadership potential and strategic thinking. The emphasis on AI tools and experience in regulated, high-stakes decision environments are key differentiators. The portfolio requirement is central, emphasizing shipped work and a deep understanding of the design process.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase end-to-end design projects for both B2B and B2C products, clearly illustrating your contribution and impact.

• Include detailed case studies that demonstrate your process for defining information architecture, conducting user research, and developing user flows.

• Present examples of how you've designed for complex, high-stakes decisions, highlighting empathy and user-centric problem-solving.

• Feature examples of your UI craft in Figma, including well-structured design systems, style guides, or component libraries.

• Provide evidence of your experience with AI/generative AI tools in your design workflow, explaining the strategic application and outcomes.

• Demonstrate ownership of projects from initial concept through to launch, with clear articulations of project goals and achieved milestones. Process Documentation:

• Clearly outline your approach to user research, including methodologies for discovery, synthesis, and validation.

• Detail your process for information architecture and ontology definition, explaining how you structure complex information for clarity and usability.

• Illustrate your workflow for creating wireframes, mockups, and interactive prototypes, showing iterative refinement based on feedback.

• Explain your methodology for building and maintaining design systems, focusing on scalability, consistency, and accessibility.

• Provide examples of how you integrate AI tools into your design process to enhance efficiency and creative output.

• Document your approach to stakeholder communication and design critique, demonstrating how you incorporate feedback to improve designs.

📝 Enhancement Note: Given this is the first staff designer role, the portfolio is crucial for demonstrating not just execution but also strategic thinking, process maturity, and the ability to influence. Emphasis on AI integration, information architecture for complex domains, and the ability to build foundational design assets (like a design system) will be key evaluation points.

💵 Compensation & Benefits

Salary Range: USD $160,000.00 - $180,000.00 per year.

• Note: This range is based on the provided salary information and aligns with senior-level Product Designer roles in the greater Philadelphia metropolitan area. Actual compensation will depend on the candidate's experience, specific location within the US, and overall performance.

Benefits:

• Comprehensive Health Insurance coverage.

• 401(k) retirement savings plan.

• Complimentary in-office food and beverages.

• Paid Public Holidays.

• Encouraged Paid Time Off (PTO).

• Eligibility for Short-Term Incentives.

• Eligibility for Long-Term Incentives.

• Equity participation in the company.

Working Hours: Standard full-time work week, likely around 40 hours, with flexibility expected. The hybrid model requires 2 days per week in the Fort Washington office.

📝 Enhancement Note: The salary range provided is specific and competitive for a senior-level design role in the specified region. The inclusion of equity, short-term, and long-term incentives suggests a strong total compensation package, particularly for a role with potential leadership growth. The hybrid arrangement with specific in-office days should be factored into the candidate's overall work-life balance considerations.

🎯 Team & Company Context

🏢 Company Culture

Industry: Financial Services (Life Settlements, Insurtech)

Company Size: Part of Coventry (founded 1982), which acquired Leopard (launched 2024). The combined entity operates with the resources of a large, established market leader and the agility of a recently integrated insurtech venture. The "Leopard" team within Coventry is likely growing rapidly.

Founded: Coventry was founded in 1982. Leopard was launched in 2024.

Team Structure:

• The Senior UX/UI Product Designer will be the first dedicated staff designer, reporting directly to the VP of Product.

• This role will operate within a growing technology organization focused on modernizing complex insurance and annuity transactions.

• Close collaboration is expected with Product Managers, Engineering teams, and other business stakeholders.

• The position offers significant influence and the potential to build and shape the design function. Methodology:

• A product-driven tech culture is being fostered, blending innovation with the stability of a market leader.

• Emphasis on AI-native platform development and modernizing complex financial transactions at scale.

• Design processes will likely evolve rapidly, requiring adaptability and a willingness to experiment with new tools and methodologies.

• Data-driven decision-making is expected, with a focus on quantitative user data and conversion optimization.

Company Website: https://www.theleopard.com/ (Note: This is derived from the domain_derived field and may represent the Leopard insurtech venture.) The primary company is Coventry.

📝 Enhancement Note: The company operates at an interesting intersection of a long-standing market leader (Coventry) and a new, venture-backed insurtech (Leopard). This implies a culture that values both established expertise and rapid innovation. The "first staff designer" role suggests an opportunity to build foundational design practices and establish a strong user-centric approach within a growing tech organization.

📈 Career & Growth Analysis

Operations Career Level: Senior Individual Contributor (Staff Designer) with clear potential for growth into a Design Lead or Managerial role as the design function expands. The scope of ownership for core user journeys and foundational systems points to a high level of responsibility.

Reporting Structure: Reports directly to the VP of Product, providing significant visibility and direct access to senior leadership. This facilitates rapid feedback loops and direct influence on product strategy.

Operations Impact: The role has a direct impact on the usability and effectiveness of both internal business operations and external consumer-facing products. By improving user experience, this role will contribute to increased operational efficiency, higher customer satisfaction, better conversion rates, and the overall success of Coventry's modernization efforts in the life insurance and annuity markets.

Growth Opportunities:

• Leadership Development: As the first staff designer, there's a clear path to grow into a leadership position, potentially building and managing a design team as the company scales its product development.

• Skill Specialization: Opportunity to deepen expertise in designing for complex, regulated industries (fintech, healthtech, insurtech), AI-driven product features, and advanced design systems.

• Strategic Influence: Contribute directly to product roadmap decisions, shaping the user-centric direction of the company's AI-native platform and core business offerings.

• Industry Exposure: Gain valuable experience in the life settlements and annuity markets, a specialized but significant segment of the financial services industry.

📝 Enhancement Note: The "first staff designer" title is a significant indicator of growth potential. The role is designed for someone who can not only execute but also lay the groundwork for future design operations and team expansion, making it an attractive opportunity for ambitious designers.

🌐 Work Environment

Office Type: Hybrid work model, requiring 2 days per week in the office located near Madison Square Garden in New York City. The company headquarters is in Fort Washington, PA, suggesting potential collaboration across locations or that "near Madison Square Garden" refers to a satellite office.

Office Location(s): Primarily Fort Washington, PA (HQ), with a significant presence or team located near Madison Square Garden, New York, NY.

Workspace Context:

• Collaborative environment with direct interaction with product and engineering teams.

• Opportunity to influence the physical and digital workspace as the design function evolves.

• Access to modern design tools and technologies, including AI and generative AI platforms.

• The office setting is likely geared towards fostering innovation and cross-functional communication.

Work Schedule: A standard full-time schedule is expected, likely with some flexibility. The hybrid model necessitates in-office presence on designated days, emphasizing a balance between remote work autonomy and in-person collaboration.

📝 Enhancement Note: The hybrid requirement, specifically "in-office two days a week near Madison Square Garden," is a key detail. It suggests a focus on in-person collaboration for key team interactions, even if the company headquarters is elsewhere. Candidates should clarify which office location they would primarily report to or if the two days can be split between locations if feasible.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Review of resume and portfolio by the hiring team to assess qualifications and experience.

• Portfolio Presentation: A dedicated session where the candidate presents their work, focusing on case studies that demonstrate problem-solving, process, and impact, particularly for B2B/B2C products and AI integration. Expect questions on how you approach complex design challenges and handle feedback.

• Cross-Functional Interviews: Meetings with Product Managers and Engineering leads to evaluate collaboration style, technical understanding, and ability to work within an agile development environment.

• Design Thinking/Problem-Solving Exercise: Potentially a take-home assignment or a live design challenge focused on a specific product problem, assessing your approach to information architecture, user flows, and UI design within the company's domain.

• VP of Product Interview: A final conversation to discuss strategic alignment, leadership potential, cultural fit, and long-term career aspirations within Leopard/Coventry.

Portfolio Review Tips:

• Curate for Impact: Select 3-5 of your strongest projects that best represent your experience with B2B and B2C products, AI integration, and complex decision-making scenarios.

• Showcase Process: For each project, clearly articulate the problem, your role, the design process (research, ideation, prototyping, testing), your specific contributions, and the measurable outcomes or impact.

• Highlight AI Integration: Dedicate specific sections or examples to showcase how you've leveraged AI/generative AI tools in your workflow, explaining the strategic value and results.

• Design System Focus: If applicable, present examples of design systems you've built or contributed to, emphasizing their structure, scalability, and impact on consistency.

• Storytelling: Frame your presentations as compelling narratives that highlight your problem-solving skills and ability to drive business value through design.

• Prepare for Questions: Anticipate questions about your design philosophy, how you handle design critiques, your experience with regulated industries, and your vision for design at Leopard.

Challenge Preparation:

• Understand the Domain: Research the life settlement and annuity markets, common user pain points, and the role of technology and AI in this space.

• Practice Information Architecture: Be ready to organize and structure information for complex financial products or internal workflows.

• Simulate AI Integration: Think about how you would design user interfaces that effectively integrate AI-driven insights or assistance.

• Focus on Clarity and Efficiency: Prepare to design solutions that simplify complex processes and improve user efficiency.

• Articulate Trade-offs: Be prepared to discuss the trade-offs involved in design decisions and justify your choices based on user needs and business goals.

📝 Enhancement Note: The interview process is likely to be rigorous, emphasizing both design craft and strategic thinking. The portfolio review will be critical, requiring candidates to clearly articulate their process and impact, especially concerning AI integration and complex domain design. The potential for a design challenge necessitates preparation in specific areas relevant to the company's industry.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Essential for wireframing, mockups, prototyping, and design system development. Proficiency is a core requirement.

• AI/Generative AI Tools: Candidates are expected to actively use and have a point of view on tools like Midjourney, Stable Diffusion, ChatGPT (for design context/ideation), or similar platforms relevant to UX/UI workflows.

• Prototyping Tools: Beyond Figma, familiarity with tools like InVision, Axure, or similar for creating interactive prototypes.

• User Research Platforms: Experience with tools for surveys, interviews, usability testing (e.g., UserTesting.com, Maze, Lookback).

Analytics & Reporting:

• Analytics Platforms: Familiarity with tools like Google Analytics, Amplitude, Mixpanel for understanding user behavior and product performance.

• Data Visualization Tools: Experience with tools like Tableau, Looker, or Power BI for interpreting and presenting user data insights.

• A/B Testing Tools: Understanding of tools and methodologies for running A/B tests to optimize user experiences.

CRM & Automation:

• CRM Systems: While not a direct CRM role, understanding of how design impacts CRM data and user management within sales or customer service platforms (e.g., Salesforce, HubSpot) is beneficial.

• Project Management Tools: Proficiency with tools like Jira, Asana, Trello for managing design tasks and collaborating with engineering.

• Design System Management Tools: Platforms or methodologies for managing and versioning design system components.

📝 Enhancement Note: The explicit mention of Figma and active use of AI/generative AI tools are critical technical requirements. While not directly a data analysis role, understanding how design impacts analytics and conversion metrics is a strong preference, indicating a data-informed design approach.

👥 Team Culture & Values

Operations Values:

• Curiosity: A drive to explore new design approaches, tools (especially AI), and user needs within a complex industry.

• Craftsmanship: High standards for visual design, interaction design, and the overall quality and polish of user experiences.

• Ownership: Taking full responsibility for design outcomes, from initial concept through to successful implementation and iteration.

• Collaboration: Working effectively with product, engineering, and business stakeholders to achieve shared goals.

• Adaptability: Embracing change and evolving processes as new tools and technologies emerge, particularly in the AI space.

• User-Centricity: Placing the needs and experiences of both internal users and external customers at the forefront of all design decisions.

Collaboration Style:

• Cross-Functional Integration: Close working relationships with Product Management and Engineering are essential for translating requirements into effective designs and ensuring seamless implementation.

• Open Communication: A culture that encourages direct feedback, constructive critique, and transparent dialogue about design decisions and challenges.

• Iterative Design: A willingness to iterate on designs based on user feedback, data analysis, and stakeholder input, fostering a continuous improvement mindset.

• Knowledge Sharing: Encouraging the sharing of design insights, best practices, and learnings across the team and with broader stakeholders.

📝 Enhancement Note: The emphasis on curiosity, craft, and ownership, particularly in the context of AI and a fast-paced startup environment, suggests a culture that values proactive contribution and continuous learning. The role of the "first staff designer" will involve actively shaping this collaborative culture.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Complexity: Navigating the intricacies of life insurance, annuities, and personal medical data, which involve high stakes, regulated environments, and potentially anxious users.

• AI Integration: Effectively incorporating AI-powered features into user interfaces in a way that is intuitive, trustworthy, and adds genuine value, rather than just being a novelty.

• Balancing Internal/External Needs: Designing for both sophisticated internal business operations tools and consumer-facing products, requiring an understanding of diverse user needs and workflows.

• Establishing Design Foundations: As the first staff designer, building out core design processes, standards, and potentially a design system from the ground up.

• Pace of Change: Adapting to a rapidly evolving tech landscape, especially with the swift advancements in AI tools and their application in design.

Learning & Development Opportunities:

• AI in Design Specialization: Becoming an expert in leveraging cutting-edge AI and generative AI tools for enhanced design productivity and innovation.

• Fintech/Insurtech Domain Expertise: Deepening knowledge in specialized financial services sectors, understanding unique user behaviors and regulatory landscapes.

• Design Leadership: Developing skills in team building, mentorship, and strategic design leadership through the growth of the design function.

• Product Strategy Influence: Gaining significant experience in shaping product roadmaps and influencing the strategic direction of a growing tech platform.

• Conversion Optimization & Data-Driven Design: Enhancing skills in using quantitative data to inform design decisions and drive measurable business outcomes.

📝 Enhancement Note: The challenges presented are directly tied to the unique aspects of the role and industry. The growth opportunities are substantial, offering a path for significant professional development in specialized areas like AI, fintech design, and leadership.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you designed a complex workflow for both internal users and external customers. What were the key differences and how did you address them?" (Focus on process, user segmentation, and trade-offs).

• "How do you approach designing user experiences for AI-powered features? What are the key considerations for trust, transparency, and user control?" (Highlight your POV on AI design principles).

• "Walk us through a project where you defined the information architecture or ontology for a new product or feature. What was your methodology and what was the outcome?" (Emphasize analytical skills and structured thinking). Company & Culture Questions:

• "What interests you about the life settlement and annuity market, and how do you see design playing a role in modernizing this industry?" (Show research and genuine interest).

• "How would you approach building a design system from the ground up in a fast-paced startup environment?" (Focus on practicality, scalability, and collaboration).

• "Describe your experience using AI/generative AI tools in your design process. How has it changed your workflow or the outcomes of your work?" (Be specific and articulate your strategic approach). Portfolio Presentation Strategy:

• Structure: For each case study, clearly present the Problem, Your Role, Process (Research, Ideation, Design, Testing), Solution, and Results/Impact.

• Visuals: Use high-quality mockups, prototypes, and diagrams to illustrate your points. Clearly label who did what if it was a team project.

• Narrative: Tell a compelling story about each project, highlighting your problem-solving skills and design thinking.

• AI Focus: Dedicate a section or specific examples to demonstrate your proficiency and strategic thinking with AI tools.

• Conciseness: Be mindful of time; prepare to present your most impactful work efficiently. Anticipate questions and have backup slides or details ready.

• Engagement: Engage with your interviewers, ask clarifying questions, and be open to their feedback during the presentation.

📝 Enhancement Note: Interview preparation should focus on demonstrating a strong understanding of the company's domain, a mature design process, proven experience with AI tools, and the ability to think strategically and lead initiatives as the first staff designer.

📌 Application Steps

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

• Submit your application through the provided link on Workable.

• Portfolio Customization: Tailor your resume and portfolio to highlight your most relevant B2B and B2C product design experience, especially projects involving complex decision-making, AI integration, or regulated industries. Ensure your portfolio clearly showcases your Figma skills and design system contributions.

• Resume Optimization: Clearly articulate your 3-7 years of experience, emphasizing end-to-end project ownership, user research methodologies, and successful product launches. Quantify achievements wherever possible.

• Prepare Your Case Studies: Rehearse presenting your portfolio projects, focusing on your unique contributions, design process, and the impact of your work, particularly concerning AI tools and complex user journeys.

• Research Coventry & Leopard: Understand the company's mission, its position in the market, and the challenges and opportunities within the life settlement and insurtech sectors. Prepare to discuss how your design philosophy aligns with their product-driven tech 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.