(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: UX/UI Design, Product Design, Operations Technology

Date Posted: June 08, 2026

Experience Level: Mid-Senior Level (3-7 years, with potential for Senior designation)

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

🚀 Role Summary

• Spearhead the end-to-end design of user experiences for both internal business operations tools and external consumer-facing platforms within the life insurance and annuity sector.

• Drive the design and implementation of AI-native features, focusing on intuitive user interaction with intelligent guidance, dynamic recommendations, and agent-driven workflows.

• Establish and evolve the product's information architecture and ontology, ensuring clarity and efficiency for both expert and novice users.

• Develop and maintain a scalable design system to ensure consistency, accessibility, and readiness for future growth across all product surfaces.

• Contribute significantly to the product roadmap through user insights and strategic design thinking, influencing the future trajectory of complex financial transactions.

📝 Enhancement Note: This role is positioned as the first staff designer, indicating significant autonomy and the potential for leadership growth. The "Senior" aspect of the title is explicitly tied to experience and performance, suggesting a need for a candidate who can not only execute but also mentor and influence design best practices across the organization. The emphasis on "AI-native platform" and "AI-powered features" highlights a forward-thinking approach to technology integration within a traditionally complex industry.

📈 Primary Responsibilities

• Lead the complete design lifecycle for core user journeys, encompassing both employee tooling and external customer interfaces, producing wireframes, mockups, and interactive prototypes.

• Define and refine the information architecture and conceptual models that govern user navigation and operational efficiency within the platform.

• Design the user experience for AI-powered functionalities, ensuring seamless integration of intelligent guidance, personalized recommendations, and automated workflows.

• Create, implement, and maintain a robust design system to ensure visual consistency, accessibility standards, and scalability across all product touchpoints.

• Collaborate closely with product management and engineering teams to translate user needs and business requirements into intuitive and effective design solutions.

• Contribute to product strategy and roadmap development by providing user insights, identifying design opportunities, and advocating for user-centered design principles.

• Educate stakeholders on design best practices, championing user experience as a critical component of business success.

📝 Enhancement Note: The responsibilities emphasize a blend of strategic thinking and hands-on execution, typical of a senior individual contributor role in a growing company. The explicit mention of "AI-native platform" and "AI-powered features" suggests a need for experience in designing with emerging technologies, particularly in areas where AI can enhance complex decision-making processes for both consumers and internal operations teams.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a Bachelor's degree in Design, HCI, Computer Science, or a related field, or equivalent practical experience, is highly recommended.

Experience: 3–7 years of professional product design experience, with a proven track record of shipping B2B and B2C products. Experience in early-stage startups is a plus.

Required Skills:

• Extensive experience in end-to-end product design, including user research, information architecture, interaction design, user flows, wireframing, prototyping, and visual design.

• Strong proficiency in Figma, including advanced features for creating production-ready designs and collaborative workflows.

• Demonstrated experience in designing for users making high-stakes decisions, particularly within regulated industries.

• Active and practical use of AI and generative AI tools in the design workflow, with a clear understanding of their impact beyond speed.

• Excellent communication and presentation skills, with the ability to articulate and defend design decisions, receive constructive feedback, and collaborate effectively in a fast-paced environment.

• Proven ability to own projects from conception to completion and deliver against project milestones.

• Deep understanding of UX fundamentals, including information architecture, interaction design, and user flow optimization.

• Strong UI craft, demonstrating expertise in typography, visual hierarchy, and spacing principles. Preferred Skills:

• Experience within the life insurance, fintech, healthtech, or other high-trust consumer product sectors where managing anxiety and decision complexity is paramount.

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

• Familiarity with conversion optimization techniques, funnel analysis, and designing based on quantitative user data.

• Experience in early-stage startup environments, demonstrating adaptability and a proactive approach.

📝 Enhancement Note: The experience requirement is framed as a range (3-7 years), with explicit mention of the "Senior aspect" being dependent on experience and performance. This implies that candidates at the higher end of this range, or those with exceptional portfolios and demonstrated leadership potential, will be strongly considered for senior compensation and responsibilities. The emphasis on AI tools is a critical differentiator.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A comprehensive portfolio showcasing shipped B2B and B2C products, demonstrating a full range of design skills from user research to live product implementation.

• Case studies that detail your process for tackling complex design problems, including user research insights, ontological decisions, wireframes, and the final product outcome.

• Examples of how you have designed for high-stakes decision-making contexts, illustrating your approach to user clarity and confidence building.

• Demonstrations of your proficiency in Figma, including complex interactive prototypes and production-ready design assets.

• Evidence of your experience leveraging AI and generative AI tools within your design process, with clear explanations of the impact on the design outcome. Process Documentation:

• Clear articulation of your design process, including how you approach user research, information architecture definition, and interaction design.

• Examples of how you have established and maintained design systems, ensuring consistency, scalability, and accessibility.

• Documentation of how you contribute to product roadmaps, integrating user insights and design thinking into strategic planning.

• Case studies that highlight your ability to own projects end-to-end, from initial concept to final delivery and iteration.

📝 Enhancement Note: The portfolio is crucial for this role, especially given it's the first staff designer position. Candidates must showcase not just visual design skills but also strategic thinking, process rigor, and the ability to handle complex financial products. Demonstrating experience with AI tools and their practical application in design is a key expectation.

💵 Compensation & Benefits

Salary Range: USD $130,000.00 to $160,000.00 annually. The final salary and the designation of "Senior" will be determined by factors such as 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, typically expected to align with a standard 40-hour work week. The hybrid model offers some flexibility, with 2 days required in the office.

📝 Enhancement Note: The salary range provided is competitive for a mid-senior to senior UX/UI Product Designer in New York City. The inclusion of short-term incentives, long-term incentives, and equity suggests a total compensation package that rewards performance and long-term commitment. The "encouraged PTO" indicates a company culture that values work-life balance, which is beneficial for demanding design roles.

🎯 Team & Company Context

🏢 Company Culture

Industry: Financial Services (Life Insurance, Annuities), Insurtech. Leopard is an insurtech incubated by The D. E. Shaw Group's venture studio, now integrated into Coventry, a market leader in life settlements. This blend offers a unique environment combining startup agility with established market presence.

Company Size: Coventry, the parent company, was founded in 1982 and has a significant market presence. Leopard, acquired in 2025, was launched in 2024. The combined entity is advancing a long-term ambition to modernize complex insurance transactions. As the first staff designer, you will be instrumental in shaping the design culture within a growing technology organization.

Founded: Coventry was founded in 1982. Leopard was launched in 2024. The integration into a unified technology organization is a recent development, indicating a dynamic and evolving environment.

Team Structure:

• The UX/UI Product Designer will be the first staff designer and will report to the VP of Product.

• Close collaboration is expected with product managers and engineering teams.

• As the team grows, there will be opportunities to influence team structure and potentially lead a design function. Methodology:

• The company is building an "AI-native platform," indicating a strong focus on leveraging artificial intelligence and machine learning for product development and operational efficiency.

• Design processes will likely involve a blend of agile methodologies, user-centered design principles, and rapid iteration, especially given the startup incubation background of Leopard.

• A focus on data-driven decision-making is implied by the mention of "quantitative user data" and "conversion optimization."

Company Website: https://jobs.workable.com/company/2huphZb2fbUBXX6WytwKy5/jobs-at-leopard (Company Careers Page)

📝 Enhancement Note: The company operates at the intersection of financial services and technology, specifically focusing on modernizing complex insurance and annuity lifecycles. This sector often involves high-stakes decisions, regulated environments, and a need for trust and clarity, making the UX/UI designer's role critical. The integration of Leopard into Coventry suggests a culture that values innovation and growth, with a desire to transform established markets.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a Mid-Senior to Senior UX/UI Product Designer. As the first staff designer, the individual will have a broad scope of influence and responsibility, laying the groundwork for design operations and potentially leading future design initiatives. This is an opportunity to transition from an individual contributor to a design leadership role within a rapidly growing and technologically focused organization.

Reporting Structure: The role reports directly to the VP of Product, providing high-level visibility and direct access to leadership. This structure allows for significant input into product strategy and design direction.

Operations Impact: The designer will directly impact the usability and effectiveness of both internal business operations tools and external customer-facing products. This includes streamlining complex financial transactions, improving user trust, and driving adoption of AI-powered features. The designer's work will be crucial in modernizing how insurance and annuity transactions are supported at scale, directly contributing to the company's strategic goals and market position.

Growth Opportunities:

• Design Leadership: With potential to grow into a Design Lead or Manager role as the team expands.

• Skill Specialization: Opportunity to deepen expertise in AI-driven design, financial services UX, and complex information architecture.

• Strategic Influence: Direct involvement in product strategy and roadmap decisions, shaping the future of the company's AI-native platform.

• Industry Expertise: Gaining specialized knowledge in life insurance, annuities, and fintech, highly valuable in the financial services sector.

• Startup Environment: Experience the fast-paced, high-impact environment of a recently integrated startup within an established market leader.

📝 Enhancement Note: The "first staff designer" title is a significant indicator of growth potential. Candidates should view this not just as a design execution role but as a foundational position from which they can build out design processes, mentor future hires, and potentially define the design team's direction. The emphasis on AI and complex financial products offers a unique specialization path.

🌐 Work Environment

Office Type: The role is hybrid, requiring presence in the office two days a week. The office is located near Madison Square Garden in New York City, suggesting a vibrant and accessible urban workspace.

Office Location(s): New York, NY. Coventry also has headquarters in Fort Washington, PA, but this specific role is based in the New York office.

Workspace Context:

• The hybrid model allows for flexibility, balancing focused remote work with in-person collaboration.

• The office environment is expected to be conducive to collaboration, with opportunities for direct interaction with product and engineering teams.

• As the first designer, you will help shape the design culture and workspace expectations.

• Access to in-office amenities like free food and drinks can enhance the daily work experience.

Work Schedule: The standard work schedule is full-time, likely aligning with typical business hours in New York City (America/New_York timezone). The hybrid nature allows for some flexibility in structuring the work week, with dedicated days for in-office collaboration.

📝 Enhancement Note: The hybrid nature of the role, with specific in-office days, is important for candidates to consider. Proximity to Madison Square Garden suggests a well-connected and desirable urban location. The company's emphasis on a "product-driven tech culture" implies an environment that values innovation and collaboration.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Likely a review of resume and portfolio to assess basic qualifications and design experience.

• Portfolio Presentation: A dedicated session where candidates present their portfolio, focusing on case studies that demonstrate their process, problem-solving skills, and impact. Expect to discuss your approach to AI tools, information architecture, and high-stakes decision design.

• Design Challenge/Case Study: A practical exercise to assess design thinking, problem-solving abilities, and proficiency with design tools (e.g., Figma). This might involve designing a specific feature or user flow.

• Team & Stakeholder Interviews: Meetings with product managers, engineers, and potentially the VP of Product to evaluate collaboration skills, communication style, and cultural fit.

• Final Interview: Likely with senior leadership to discuss overall fit, experience level, and alignment with company vision.

Portfolio Review Tips:

• Highlight AI Integration: Clearly showcase how you've used generative AI tools and their specific impact on your design outcomes, not just efficiency gains.

• Emphasize Process: Detail your design methodology, from user research and information architecture to iteration and final implementation. Use clear visuals to explain complex flows.

• Focus on Impact: Quantify your achievements where possible (e.g., "improved conversion by X%", "reduced task completion time by Y%"). For this role, focus on how your designs simplify complex financial decisions and improve operational efficiency.

• Showcase B2B & B2C: Provide examples that demonstrate your ability to design for both internal operational tools and external consumer-facing products.

• Design for Complexity: Include examples where you've designed for users making high-stakes decisions, explaining how you built trust and clarity.

• Figma Proficiency: Ensure your prototypes are well-crafted and interactive, demonstrating your mastery of the tool.

Challenge Preparation:

• Understand the Domain: Research life settlements, annuities, and the broader fintech/insurtech landscape. Familiarize yourself with common user pain points and regulatory considerations.

• AI Application: Be prepared to discuss how AI can be applied to solve problems in this domain, and how you would design user interfaces for AI-driven insights and recommendations.

• Information Architecture: Practice structuring complex information logically for both user types (internal operations, external consumers).

• Communication: Prepare to articulate your design rationale clearly and concisely, as well as defend your decisions and incorporate feedback constructively.

📝 Enhancement Note: The interview process emphasizes practical demonstration of skills and strategic thinking. The portfolio review is a critical component, and candidates should tailor their presentations to highlight experience with AI tools, complex financial products, and both B2B/B2C design.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: This is explicitly mentioned as a required skill for UI craft and production-ready designs. Expect to use it for wireframing, prototyping, UI design, and design system management.

• Prototyping Tools: Beyond Figma's capabilities, experience with other prototyping tools may be beneficial for more complex interactions.

• User Research Tools: Tools for conducting user interviews, surveys, and usability testing (e.g., UserTesting.com, SurveyMonkey, Maze).

• AI & Generative AI Tools: Candidates are expected to be actively using these tools in their workflow (e.g., Midjourney, Stable Diffusion, AI assistants for content generation/ideation).

Analytics & Reporting:

• Analytics Platforms: Experience with web analytics tools (e.g., Google Analytics, Mixpanel, Amplitude) to understand user behavior and conversion funnels.

• Data Visualization Tools: Familiarity with tools for creating dashboards and reports to communicate insights (e.g., Tableau, Looker, Power BI) could be advantageous.

CRM & Automation:

• CRM Systems: While not explicitly mentioned, understanding CRM principles (e.g., Salesforce, HubSpot) is beneficial given the B2B aspect of the business and potential integration with internal operations.

• Workflow Automation Tools: Familiarity with how automation impacts user workflows, especially in complex financial processes, would be a plus.

📝 Enhancement Note: Figma is the cornerstone tool. The emphasis on AI and generative AI tools is a strong signal that candidates should be prepared to discuss their specific applications and the candidate's perspective on their evolving role in design. Understanding how design integrates with data analytics for conversion optimization is also highlighted.

👥 Team Culture & Values

Operations Values:

• Curiosity & Craft: A drive to explore new design approaches and a commitment to high-quality execution.

• Ownership: Taking responsibility for design outcomes and driving projects to completion.

• Adaptability: Flexibility to embrace new tools and methodologies as the industry and technology evolve (e.g., AI tools).

• Data-Driven Insights: Utilizing user data and analytics to inform design decisions and measure impact.

• User-Centricity: Prioritizing the needs and experiences of both internal operators and external consumers.

• Collaboration: Working effectively with cross-functional teams to achieve shared goals.

Collaboration Style:

• Cross-Functional Integration: Close partnership with Product and Engineering is essential for successful product development.

• Feedback Exchange: An open culture where constructive feedback is welcomed and acted upon.

• Fast-Paced Environment: The ability to work efficiently and adapt quickly to changing priorities.

• Stakeholder Education: A willingness to educate and evangelize design principles to non-design stakeholders.

📝 Enhancement Note: The company culture appears to value innovation, pragmatism, and a strong sense of ownership. As the initial designer, contributing to and shaping this culture will be a key aspect of the role. The emphasis on AI tools suggests a forward-looking and experimental mindset.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Complexity: Creating intuitive interfaces for complex financial products (life insurance, annuities) and high-stakes decisions.

• AI Integration: Effectively designing user experiences for AI-powered features, managing user expectations, and ensuring trust in AI-driven guidance.

• Balancing B2B & B2C: Designing for two distinct user groups with potentially different needs, workflows, and technical proficiencies.

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

• Navigating a Hybrid Environment: Maximizing collaboration and productivity across remote and in-office workdays.

Learning & Development Opportunities:

• AI Design Specialization: Becoming an expert in designing AI-native products and human-AI interaction.

• Fintech/Insurtech Domain Expertise: Developing deep knowledge in a specialized and high-value industry.

• Leadership Development: Opportunities to grow into a design leadership role, mentoring junior designers and shaping team strategy.

• Cross-Functional Acumen: Deepening understanding of product management and engineering processes within a tech-driven financial services company.

• Startup Dynamics: Gaining experience in a fast-paced, evolving environment with significant impact potential.

📝 Enhancement Note: The challenges presented are common in innovative tech companies, particularly those in regulated industries. The growth opportunities are substantial, especially for an individual looking to grow into a leadership position and specialize in a rapidly evolving field like AI-driven design.

💡 Interview Preparation

Strategy Questions:

• "Describe a complex B2B operational tool you designed. What were the key challenges, and how did your design address them?" (Focus on information architecture, workflow optimization, and user efficiency).

• "How do you approach designing for users making high-stakes financial decisions? Walk us through a relevant case study." (Highlight user research, trust-building elements, and clarity in communication).

• "How have you integrated AI or generative AI tools into your design process? What was the impact on your workflow and the final product?" (Be specific about tools used and outcomes achieved).

• "Walk us through your process for creating and maintaining a design system. What are the key components, and how do you ensure adoption?" (Showcase your understanding of scalability and consistency).

• "How would you prioritize design requests from both internal operations teams and external customers when resources are limited?" (Demonstrate strategic thinking and prioritization skills). Company & Culture Questions:

• "What interests you about the life insurance/annuity industry and Coventry's mission?" (Show research and genuine interest).

• "How do you see AI transforming the insurance industry, and what role does design play in that transformation?" (Align with company's AI-native vision).

• "Describe a time you had to educate stakeholders on design best practices. What was your approach, and what was the outcome?" (Demonstrate influence and communication skills).

• "How do you handle constructive criticism on your designs?" (Show resilience and openness to feedback).

• "What are your expectations for collaboration with product managers and engineers?" (Highlight your teamwork approach). Portfolio Presentation Strategy:

• Tell a Story: Structure your case studies as narratives, explaining the problem, your process, your role, and the solution's impact.

• Visual Clarity: Use high-quality visuals (wireframes, mockups, prototypes) and avoid clutter. Ensure your Figma skills are evident.

• Focus on Process: Dedicate time to explaining your thought process, research findings, and design decisions.

• Quantify Impact: Whenever possible, present metrics that demonstrate the success of your designs.

• AI Integration: Clearly highlight your AI-related projects and the unique contributions they represent.

• Conciseness: Be mindful of time constraints. Practice your presentation to ensure it's impactful and within the allotted timeframe.

📝 Enhancement Note: Interview preparation should focus on demonstrating a deep understanding of UX fundamentals, practical application of AI tools, and the ability to design for complex, regulated industries. Highlighting experience with both B2B operations tools and B2C customer interfaces will be key.

📌 Application Steps

To apply for this operations position:

• Submit your application through the provided link on Workable.

• Portfolio Customization: Ensure your portfolio prominently features case studies relevant to complex financial products, AI integration, and both B2B/B2C design. Tailor your presentation to highlight your process and impact.

• Resume Optimization: Update your resume to emphasize keywords such as UX Design, UI Design, Product Design, Figma, Information Architecture, Interaction Design, AI Tools, Generative AI, B2B, B2C, and experience in financial services or regulated industries. Quantify achievements where possible.

• Interview Preparation: Practice articulating your design process, decision-making rationale, and experience with AI tools. Prepare to present your portfolio effectively and be ready for a design challenge.

• Company Research: Thoroughly research Coventry and Leopard, understanding their market position, mission, and the challenges of modernizing the life insurance and annuity lifecycle. Familiarize yourself with their AI-native platform vision.

⚠️ 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.