Senior UX/UI Product Designer

📍 Job Overview

Job Title: Senior UX/UI Product Designer

Company: Leopard (part of Coventry)

Location: New York, New York, United States

Job Type: FULL_TIME

Category: Product Design / UX/UI

Date Posted: 2026-08-06

Experience Level: 5-10 years (implied by 3-7 years requirement and seniority of role)

Remote Status: Hybrid (2 days in-office)

🚀 Role Summary

• Spearhead end-to-end design for complex user journeys, encompassing both internal business operations tools and external customer-facing interfaces.

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

• Establish the foundational design principles for integrating AI-powered features, focusing on user interaction with intelligent guidance and automated workflows.

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

• Contribute to product strategy and roadmap development through user insights and innovative design thinking.

📝 Enhancement Note: This role is positioned as the "first staff designer," indicating significant influence and potential for leadership growth. The emphasis on AI-native platform design and a hybrid work model suggests a modern, forward-thinking product development environment. The target candidate is expected to be a proactive driver of design culture and best practices.

📈 Primary Responsibilities

• Own the complete design lifecycle for core user journeys, translating complex business operations use cases and external customer needs into intuitive wireframes, mockups, and interactive prototypes.

• Architect the information hierarchy and semantic structure of product interfaces, defining labels, categories, and conceptual models to optimize user comprehension and task completion.

• Design user experiences for AI-driven functionalities, ensuring seamless integration of intelligent guidance, personalized recommendations, and agent-assisted workflows for both internal and external users.

• Create, manage, and evolve a comprehensive design system that enforces visual consistency, adheres to accessibility standards, and supports future product expansion.

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

• Educate stakeholders on design best practices, advocating for user-centered design principles throughout the product development process.

📝 Enhancement Note: The responsibilities highlight a broad scope, covering both B2B (internal tools) and B2C (external interfaces) design. The specific mention of "life insurance, annuities, and personal medical data spaces" points to a need for sensitivity and clarity in designing for high-stakes, regulated industries.

🎓 Skills & Qualifications

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

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

Required Skills:

• Demonstrated expertise in UX fundamentals, including information architecture, interaction design, user flows, and user research methodologies.

• Proficiency in designing for users navigating high-stakes decisions and complex information environments.

• Advanced UI design craft in Figma, with a strong command of typography, visual hierarchy, spacing, and creating production-ready design assets.

• Active and demonstrated use of AI and generative AI tools within the design workflow, with a clear perspective on their impact beyond mere speed improvements.

• Exceptional communication and presentation skills, capable of articulating and defending design decisions, receiving constructive feedback, and collaborating effectively in a fast-paced environment.

• Proven ability to own projects from inception to completion, consistently meeting project milestones and delivering high-quality outcomes. Preferred Skills:

• Experience within regulated industries such as life insurance, fintech, or healthtech, particularly in areas involving high trust and complex decision-making.

• Background in content design, UX writing, or applying plain language principles in regulated sectors.

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

• Familiarity with conversion optimization techniques, funnel analysis, and designing data-informed user experiences using quantitative user data.

📝 Enhancement Note: The emphasis on AI tools and experience in regulated industries suggests a need for candidates who are not only skilled designers but also strategic thinkers capable of navigating complex domain challenges and leveraging emerging technologies. The "first staff designer" aspect implies a need for self-starters who can define processes as well as execute them.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A robust portfolio showcasing shipped B2B and B2C products, detailing end-to-end design processes.

• Clear examples of user research methodologies employed and how insights informed design decisions.

• Demonstrations of information architecture and ontological decisions made for complex product surfaces.

• Visual documentation of wireframes, mockups, and interactive prototypes that illustrate user flow and interaction design.

• Evidence of live products designed, highlighting the impact and success of your contributions. Process Documentation:

• Detailed case studies illustrating the application of design thinking and user-centered design principles in problem-solving.

• Documentation of how AI and generative AI tools were integrated into the design workflow, with specific examples of their impact on the design outcome.

• Examples of established or evolved design systems, showcasing consistency, scalability, and component-level design.

• Demonstrations of how user insights and data were leveraged to iterate on designs and improve key metrics.

📝 Enhancement Note: Given the role's seniority and the "first staff designer" context, the portfolio should not only showcase design output but also the candidate's strategic thinking, process ownership, and ability to influence product direction and design culture. Emphasis should be placed on how AI tools were leveraged and how the candidate established foundational design practices.

💵 Compensation & Benefits

Salary Range: USD $160,000.00 - $180,000.00 per year. This range is based on experience, location, and performance.

Benefits:

• Comprehensive health insurance coverage.

• 401(k) retirement savings plan.

• Complimentary in-office food and drinks.

• Paid holidays and encouraged Paid Time Off (PTO).

• Eligibility for short-term and long-term incentives.

• Equity participation in the company.

Working Hours: Standard full-time hours, estimated at 40 hours per week, with a hybrid arrangement requiring 2 days per week in the New York office.

📝 Enhancement Note: The salary range is competitive for a Senior UX/UI Product Designer in New York City. The inclusion of incentives and equity suggests a performance-driven culture and an opportunity for significant long-term financial gain. The hybrid model with specific in-office days indicates a structured approach to work-life integration.

🎯 Team & Company Context

🏢 Company Culture

Industry: The company operates within the Insurtech sector, with a specific focus on life settlements, life insurance, and annuities. This is a domain that involves complex financial products, high-stakes decisions for consumers, and a need for trust and regulatory compliance. The integration of AI and a product-driven tech culture are key differentiators.

Company Size: Leopard, now integrated into Coventry, is part of a larger, established organization (Coventry, founded in 1982). Leopard itself was incubated by The D. E. Shaw Group’s venture studio and launched in 2024, suggesting a dynamic, growth-oriented environment with the backing of a significant entity. This combination offers the agility of a startup with the stability of a market leader.

Founded: Coventry was founded in 1982, establishing the life settlement market. Leopard was launched in 2024. This blend of established market leadership and recent innovation creates a unique cultural dynamic.

Team Structure:

• The UX/UI Product Designer will be the first dedicated staff designer, reporting to the VP of Product. This implies a lean, high-impact team structure.

• The role involves close collaboration with product managers and engineering teams, suggesting a cross-functional, agile development approach.

• Expectation to educate stakeholders indicates a need for strong advocacy and influence within the organization. Methodology:

• The company emphasizes an AI-native platform approach, integrating generative AI and LLMs into their product development.

• A "product-driven tech culture" suggests a focus on user needs, data-driven decision-making, and iterative development processes.

• The design process will likely involve a blend of traditional UX/UI methodologies and cutting-edge AI design applications, requiring adaptability and continuous learning.

Company Website: https://www.theleopard.com/ (implied by domain_derived) and Coventry's main site (https://www.coventry.com/)

📝 Enhancement Note: The company culture appears to be a blend of established financial services expertise and modern tech innovation. The "first staff designer" position suggests an opportunity to shape the design function and culture from its early stages, requiring strong leadership potential and a proactive mindset.

📈 Career & Growth Analysis

Operations Career Level: This is a Senior Product Designer role, implying a high level of autonomy, responsibility, and expected impact. As the "first staff designer," the individual will be instrumental in defining and scaling the design function.

Reporting Structure: The role reports directly to the VP of Product, indicating significant visibility and direct access to leadership. This structure allows for direct influence on product strategy and decision-making.

Operations Impact: The designer will directly impact the user experience of both internal business operations and external customer-facing products. This includes shaping how users interact with complex financial products and AI-driven features, directly influencing customer satisfaction, operational efficiency, and ultimately, business growth.

Growth Opportunities:

• Leadership Development: The "first staff designer" role offers a clear path to team leadership as the design function grows. This includes potentially managing future designers, establishing design processes, and mentoring junior team members.

• Skill Specialization: Opportunity to deepen expertise in AI-driven design, complex financial product UX, and potentially UX writing/content design within regulated industries.

• Strategic Influence: Direct involvement in product roadmap and strategy discussions provides a platform to influence the company's direction and develop strategic thinking skills.

• Innovation: Working with cutting-edge AI tools and in a transformative industry provides opportunities to pioneer new design approaches and solutions.

📝 Enhancement Note: The growth trajectory is significant, moving beyond individual contribution to potential team leadership and strategic product influence. Candidates should be motivated by the opportunity to build and shape a design function within a growing, innovative company.

🌐 Work Environment

Office Type: The role requires hybrid work, with 2 days per week spent in the office located near Madison Square Garden in New York City. This suggests a collaborative office environment designed to foster in-person interaction and team cohesion.

Office Location(s): New York, NY. This prime location offers access to a vibrant ecosystem of talent and resources.

Workspace Context:

• The office environment likely supports collaborative work, with opportunities for brainstorming, design critiques, and cross-functional team meetings.

• As a tech-focused company, expect access to modern design tools and potentially advanced hardware.

• The hybrid model allows for focused, independent work at home, balanced with in-person collaboration and team building.

Work Schedule: The role is full-time, with an estimated 40 working hours per week. The hybrid arrangement provides some flexibility in how the work week is structured, balancing in-office and remote days.

📝 Enhancement Note: The hybrid model is designed to balance focused work with collaborative synergy. The emphasis on in-office days near a major landmark suggests a commitment to fostering a strong team culture and facilitating spontaneous collaboration.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio to assess qualifications and alignment with the role's requirements. Prepare to highlight your most relevant B2B/B2C projects and your experience with AI tools.

• Design Challenge/Case Study: You may be asked to complete a take-home design challenge or present a detailed case study from your portfolio, focusing on problem-solving, process, and impact. Be ready to articulate your design decisions and the rationale behind them.

• Stakeholder Interviews: Interviews with the VP of Product and potentially engineering leads to assess your technical skills, design craft, communication abilities, and cultural fit. Be prepared to discuss your experience working in fast-paced environments and collaborating with technical teams.

• Final Interview: Potentially with senior leadership to discuss strategic fit and long-term potential within the company.

Portfolio Review Tips:

• Curate Strategically: Select 3-4 of your strongest projects that best demonstrate your end-to-end design process, your experience with complex problems (especially in regulated or high-stakes domains), and your proficiency with AI tools.

• Show Your Process: For each project, clearly articulate the problem, your role, the research and discovery phase, design iterations, key decisions (especially ontological and IA), your use of AI, and the final outcome/impact. Quantify results where possible.

• Highlight AI Integration: Explicitly detail how you utilized AI and generative AI tools, what the benefits were, and how they shaped your design decisions or outcomes.

• Visual Clarity: Ensure your mockups, wireframes, and prototypes are well-presented and easy to understand. Explain the rationale behind your visual design choices.

• Storytelling: Frame your projects as compelling narratives that showcase your problem-solving skills, creativity, and ability to deliver impactful solutions.

Challenge Preparation:

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

• Focus on Process: If given a challenge, emphasize your structured approach to understanding the problem, defining requirements, exploring solutions, and iterating based on feedback.

• AI Integration: Consider how AI could be applied to the challenge problem, even if not explicitly stated, and be ready to discuss its potential.

• Communication: Practice articulating your thought process clearly and concisely, as if presenting to product and engineering stakeholders.

📝 Enhancement Note: The interview process will heavily weigh your portfolio and your ability to articulate your design process, particularly concerning AI integration and handling complex domains. Demonstrating self-sufficiency and a proactive approach to building design culture will be key.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Essential for wireframing, UI design, prototyping, and collaboration. Proficiency is a must.

• Generative AI Tools: Experience with tools like Midjourney, Stable Diffusion, ChatGPT (for design-related tasks), or similar generative AI platforms is expected.

• Prototyping Tools: Beyond Figma's capabilities, familiarity with tools like InVision, Principle, or Axure may be beneficial for complex interactions.

Analytics & Reporting:

• Familiarity with product analytics platforms (e.g., Amplitude, Mixpanel, Google Analytics) to understand user behavior and inform design decisions.

• Experience with A/B testing tools to validate design hypotheses. CRM & Automation:

• While not directly a CRM role, understanding how design integrates with CRM systems (e.g., Salesforce, HubSpot) and marketing automation platforms can be advantageous for B2B tools.

• Familiarity with project management tools like Jira, Asana, or Trello for workflow management.

📝 Enhancement Note: The core technology stack revolves around Figma and advanced AI design tools. A strong understanding of how design integrates with data analytics and project management workflows is crucial for this role, especially in defining internal business tools.

👥 Team Culture & Values

Operations Values:

• Curiosity: A drive to explore new tools, technologies (especially AI), and user needs.

• Craftsmanship: A commitment to high standards in design execution, attention to detail, and user experience quality.

• Ownership: Taking responsibility for projects end-to-end, from conception to delivery and iteration.

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

• User-Centricity: A deep commitment to understanding and serving the needs of both consumers and business users.

Collaboration Style:

• Cross-functional Integration: Working closely with product managers and engineers in an agile environment.

• Open Communication: Presenting and defending design decisions, while being receptive to feedback and iterative improvements.

• Educating Stakeholders: Proactively sharing design knowledge and best practices across the organization.

• Hybrid Synergy: Balancing focused individual work with collaborative in-person sessions.

📝 Enhancement Note: The company values suggest a culture that embraces innovation, high-quality execution, and personal accountability. The "first staff designer" will play a key role in embodying and promoting these values within the design function and across product teams.

⚡ Challenges & Growth Opportunities

Challenges:

• Defining Design Culture: As the first staff designer, establishing and scaling the design function, processes, and culture will be a primary challenge.

• AI Integration Complexity: Navigating the rapidly evolving landscape of AI tools and effectively integrating them into user-facing products and internal workflows requires continuous learning and strategic foresight.

• Complex Domain: Designing for regulated industries like life insurance and annuities involves significant constraints, ethical considerations, and the need for extreme clarity and trust.

• Balancing B2B & B2C: Simultaneously designing for internal business operations tools and external customer interfaces requires managing diverse user needs and use cases.

Learning & Development Opportunities:

• AI Design Specialization: Deepen expertise in leveraging AI for design ideation, iteration, and workflow optimization.

• Industry Expertise: Gain in-depth knowledge of the life insurance and annuity markets, understanding their unique user needs and regulatory environments.

• Leadership Skills: Develop team leadership and management capabilities as the design team expands.

• Product Strategy: Enhance strategic thinking by contributing directly to the product roadmap and long-term vision.

📝 Enhancement Note: The challenges presented are significant but directly correlate with substantial growth opportunities. Candidates who thrive in ambiguity, are eager to pioneer new approaches, and possess strong problem-solving skills will find this role highly rewarding.

💡 Interview Preparation

Strategy Questions:

• "How would you approach defining the initial design process and culture for a growing product team as the first dedicated designer?" - Preparation: Focus on your experience in establishing processes, advocating for design, and building cross-functional relationships.

• "Describe a time you designed for a complex, regulated industry. What were the key challenges and how did you ensure user trust and clarity?" - Preparation: Use a STAR method example, emphasizing research, stakeholder management, and clear communication strategies.

• "How have you integrated AI or generative AI tools into your design workflow? What was the impact on your process and the final product?" - Preparation: Be specific about the tools used, the problems they solved, and the tangible outcomes. Discuss your perspective on AI's future in design.

• "Walk us through a project where you owned the end-to-end design of a user journey, from research to shipped product." - Preparation: Select a strong portfolio piece and be ready to articulate every stage of your process, your decisions, and the results. Company & Culture Questions:

• "What are your thoughts on the hybrid work model and how do you ensure effective collaboration in this environment?" - Preparation: Discuss strategies for maximizing in-office days and maintaining connection remotely.

• "How do you stay current with emerging design trends and technologies, particularly in the AI space?" - Preparation: Mention specific resources, communities, or learning habits.

• "What does 'ownership' mean to you in a product design context?" - Preparation: Connect this to your experience taking initiative and driving projects to completion. Portfolio Presentation Strategy:

• Start with Impact: Begin by clearly stating the problem and the key outcomes of your project.

• Show, Don't Just Tell: Use visuals (wireframes, mockups, prototypes) to illustrate your design process and solutions.

• Explain Your 'Why': Articulate the rationale behind your design decisions, especially how user research and AI insights informed them.

• Quantify Success: Whenever possible, use data and metrics to demonstrate the impact of your work.

• Highlight AI Use: Dedicate specific slides or sections to showcase how you leveraged AI tools and the benefits derived.

📝 Enhancement Note: Expect a rigorous interview process that tests your design skills, strategic thinking, communication abilities, and cultural fit. Be prepared to demonstrate not only your technical proficiency but also your ability to lead and influence 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 portfolio to highlight your most relevant B2B/B2C projects, specifically emphasizing your experience with AI tools, complex domains (like finance/healthtech), and end-to-end design ownership.

• Resume Optimization: Ensure your resume clearly articulates your 3-7 years of experience, key skills (Figma, IA, interaction design, AI integration), and quantifiable achievements. Use keywords from the job description.

• Interview Preparation: Practice presenting your portfolio projects, focusing on your design process, decision-making, and the impact of your work, especially concerning AI. Prepare answers to common behavioral and situational questions.

• Company Research: Deeply understand Coventry and Leopard's mission, market position, and the challenges they aim to solve with their AI-native platform. Consider how your design philosophy aligns with their stated values.

⚠️ 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.