Sr. Product Designer

📍 Job Overview

Job Title: Sr. Product Designer

Company: Jerry.ai

Location: Palo Alto, California, United States

Job Type: Full-Time

Category: Product Design / UX/UI

Date Posted: May 18, 2026

Experience Level: 5+ Years

🚀 Role Summary

• Drive the end-to-end design process for Jerry's core products, focusing on simplifying complex car ownership experiences through intuitive UX/UI.

• Translate data-heavy insights and product requirements into clear user flows, wireframes, prototypes, and high-fidelity visuals for both mobile and web platforms.

• Collaborate closely with Product Managers, Engineers, and Data Scientists to define user problems and design solutions that deliver measurable business outcomes and a delightful user experience.

• Contribute to the evolution and refinement of Jerry's design system, ensuring consistency and scalability across all product touchpoints.

• Leverage user research, analytics, and experimentation to inform design decisions and validate design approaches, embodying a data-informed design philosophy.

📝 Enhancement Note: This role is situated within a fast-paced, growth-stage tech company that is disrupting a massive, traditional industry (automotive/insurance). The emphasis on "AI-powered assistant" and "simplifying complex data" points towards a need for designers who can not only create beautiful interfaces but also effectively manage and present intricate information in a user-friendly manner. The "revenue operations" context is inferred from the company's focus on profitability and growth targets, suggesting that design decisions will be closely tied to business objectives and user engagement metrics.

📈 Primary Responsibilities

• Partner with Product Managers and Engineering teams to deeply understand user problems, identify opportunities for simplification, and collaboratively design innovative solutions.

• Lead UX explorations for complex challenges, architecting intuitive workflows that make car ownership and management feel effortless for millions of users.

• Develop comprehensive design documentation, including user flows, wireframes, interactive prototypes, and polished UI designs for new features and product enhancements.

• Utilize a combination of user research methodologies, product analytics, and A/B testing results to inform design decisions and iterate on existing features.

• Actively contribute to the growth and maintenance of Jerry's design system, ensuring adherence to brand guidelines and promoting design consistency across the product suite.

• Strategically apply AI capabilities to enhance user clarity, personalize experiences, and automate processes within the Jerry platform.

• Conduct design reviews to share work, solicit feedback, and ensure alignment with product strategy and business goals.

📝 Enhancement Note: The responsibilities highlight a need for a designer who can operate independently across the entire design lifecycle, from initial problem definition to final UI implementation. The mention of "measurable outcomes" and "leveraging research, analytics, and experimentation" implies a strong link between design work and business impact, a key characteristic of roles within a revenue-focused or growth-oriented operations framework.

🎓 Skills & Qualifications

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

Experience: Minimum of 5 years of professional experience in product design, with a significant focus on consumer-facing mobile or web applications. Agency or in-house experience is acceptable.

Required Skills:

• A robust portfolio showcasing strong UX thinking, data-informed decision-making, and the creation of clean, intuitive interface designs for consumer products.

• Proven ability to translate complex product requirements and data into simple, elegant, and user-friendly workflows.

• Proficiency in industry-standard design and prototyping tools, with a strong emphasis on Figma.

• Experience in defining, using, and evolving design systems to ensure product consistency and scalability.

• Excellent communication and presentation skills, with the ability to articulate design rationale effectively to diverse stakeholders, including technical and non-technical teams.

• Demonstrated experience collaborating effectively with Product Managers, Engineers, and Data Scientists in an agile environment.

Preferred Skills:

• Experience within marketplaces, fintech, insurance, or mobility sectors.

• Familiarity with AI/ML applications in product design.

• Experience designing for both iOS and Android platforms.

• A strong understanding of accessibility standards and best practices.

📝 Enhancement Note: The requirement for 5+ years of experience and a strong portfolio with "data-informed decision making" and "clean, intuitive interface design" suggests a mid-to-senior level role. The emphasis on translating "complex data and product requirements into simple, elegant workflows" is particularly relevant for operations-minded candidates who understand the importance of process simplification and efficiency. The mention of "marketplaces, fintech, insurance, or mobility" as bonus points indicates a preference for candidates with domain expertise that can accelerate their impact.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase a minimum of 3-5 distinct projects demonstrating end-to-end product design ownership, from problem identification to final UI.

• Clearly articulate the UX challenges, your design process, and the rationale behind your design decisions for each project.

• Highlight projects that involve simplifying complex information or data into intuitive user experiences.

• Include case studies that demonstrate how you leveraged user research, data analytics, or A/B testing to inform your design and drive measurable outcomes.

Process Documentation:

• For each project, detail the specific design methodologies and tools used (e.g., user interviews, usability testing, Figma, prototyping tools).

• Explain your approach to collaborating with cross-functional teams (PMs, Engineers, Data Scientists) throughout the design process.

• Illustrate your understanding of design systems and how you've applied or contributed to them in previous roles.

• Demonstrate how your design solutions have led to tangible improvements, such as increased user engagement, conversion rates, or task completion efficiency.

📝 Enhancement Note: For a Senior Product Designer role, a portfolio is crucial. The emphasis here is not just on visual design but on the strategic thinking and process behind it. Candidates should be prepared to walk through their portfolio and discuss how their design choices directly impacted user behavior and business objectives, aligning with the operational focus on measurable results and efficiency.

💵 Compensation & Benefits

Salary Range: $150,000 - $200,000 USD per year.

Benefits:

• Comprehensive health, dental, and vision coverage.

• Generous paid time off (PTO).

• Paid parental leave.

• 401(K) plan with employer matching.

• Wellness benefits.

• Opportunity for equity grants.

Working Hours: Standard full-time work hours, likely around 40 hours per week, with flexibility expected in a remote or hybrid work environment.

📝 Enhancement Note: The salary range provided is competitive for a Senior Product Designer in the Palo Alto/Bay Area, reflecting the experience level and the company's growth stage. The inclusion of equity grants suggests that the company is looking for individuals who are invested in its long-term success, a common characteristic in high-growth tech environments. The benefits package is robust and typical for a full-time role in the US tech industry.

🎯 Team & Company Context

🏢 Company Culture

Industry: Automotive Tech / Insurtech / Fintech. Jerry.ai operates at the intersection of these industries, leveraging technology to simplify car ownership. This is a rapidly evolving and highly competitive market.

Company Size: Mid-sized, post-profitability tech company with significant funding ($240M) and ambitious growth targets ($10B by 2030). This indicates a dynamic environment with potential for rapid scaling and impact.

Founded: 2017. The company has moved beyond the startup phase and is now focused on scaling operations and refining its product, having achieved profitability.

Team Structure:

• The design team is led by Kruise Sapstein (Head of Design), aiming to build a high-craft, high-performing culture.

Methodology:

• Data-informed decision making is a core tenet, with a strong emphasis on leveraging research, analytics, and experimentation.

• AI and machine learning are central to the company's product strategy, aiming to provide personalized and automated solutions.

• A focus on user experience to simplify complex processes is paramount, as evidenced by the company's mission to make car ownership effortless.

Company Website: https://www.jerry.ai

📝 Enhancement Note: Jerry.ai is positioned as a disruptor in a large, traditional market. The company's success (profitability, significant funding) suggests a mature yet agile operational framework. The emphasis on AI and a "super app" approach indicates a forward-thinking, technology-driven culture. The described team structure points to a highly collaborative environment where designers work hand-in-hand with product and engineering.

📈 Career & Growth Analysis

Operations Career Level: This role is for a Senior Product Designer, indicating a level of autonomy and influence. It requires not only strong design skills but also the ability to mentor others and contribute to strategic product discussions. The "5+ years of experience" requirement solidifies this mid-to-senior designation.

Reporting Structure: The Senior Product Designer will report to Kruise Sapstein, Head of Design, and will work closely with Product Managers, Engineers, and Data Scientists. This direct reporting line to leadership suggests opportunities for significant mentorship and visibility.

Operations Impact: Design at Jerry.ai is central to simplifying car ownership and driving user adoption, retention, and satisfaction. The design team's work directly influences customer acquisition (through intuitive onboarding), engagement (through personalized experiences), and retention (through seamless management of car-related needs). This directly impacts the company's revenue and growth trajectory by making the product more accessible and valuable to a wider audience.

Growth Opportunities:

• Skill Advancement: Opportunities to deepen expertise in UX/UI design, AI-driven design applications, and complex data visualization.

• Leadership Potential: Potential to grow into a Lead Designer role, mentor junior designers, and contribute more significantly to design strategy and team culture.

• Domain Expertise: Develop deep knowledge in the automotive, insurance, and fintech sectors, becoming a subject matter expert.

• Cross-Functional Leadership: Gain experience leading design initiatives in close partnership with product management, engineering, and data science teams, fostering a strong understanding of GTM strategies.

📝 Enhancement Note: The role offers significant growth potential, moving beyond pure execution to strategic contribution. The emphasis on impact and collaboration suggests that successful designers will not only create great products but also contribute to the operational efficiency and strategic direction of the company.

🌐 Work Environment

Office Type: While the job listing has "TELECOMMUTE" as the location type and lists "Remote OK", the company headquarters are in Palo Alto, California. This suggests a company that is embracing remote or hybrid work models, but likely has a physical presence or strong ties to the Bay Area.

Office Location(s): The company is headquartered in Palo Alto, California. The remote options listed suggest flexibility, with potential candidates considered across the United States.

Workspace Context:

• Collaborative Environment: The role emphasizes close collaboration with PMs, engineers, and data scientists, suggesting a dynamic and interactive work environment where design is integrated into the broader product development process.

• Tools and Technology: Access to industry-standard design tools like Figma and rapid prototyping software will be essential. The company's use of AI and data analytics will likely influence the types of tools and data available to designers.

• Operations Integration: Designers will work within a data-driven framework, requiring them to be comfortable with analytics and performance metrics to inform their design decisions and demonstrate impact.

Work Schedule: Full-time with flexibility, characteristic of tech companies that support remote or hybrid work. This allows for effective collaboration across different time zones and provides work-life balance.

📝 Enhancement Note: The "TELECOMMUTE" classification with "Remote OK" indicates a strong remote-first or remote-friendly culture, which is a significant draw for many operations professionals seeking flexible work arrangements. The context implies a modern, digitally-enabled workspace that prioritizes collaboration and efficient communication.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Review of resume and portfolio to assess experience, skills, and alignment with the role's requirements.

• Portfolio Presentation & Design Exercise: Candidates will likely present their portfolio, discussing key projects, design process, and impact. This may be followed by a design challenge or take-home assignment to evaluate problem-solving skills and design execution.

• Cross-Functional Interviews: Interviews with Product Managers, Engineers, and potentially other designers to assess collaboration style, communication skills, and technical understanding.

• Leadership Interview: Meeting with the Head of Design (Kruise Sapstein) and potentially the CEO/Head of Product (Art Agrawal) to discuss strategic thinking, culture fit, and overall vision.

Portfolio Review Tips:

• Curate Strategically: Select projects that best showcase your UX thinking, data-informed decision-making, and ability to simplify complex problems. Focus on quality over quantity.

• Tell a Story: For each project, clearly articulate the problem, your role, the process you followed, the decisions you made, and the measurable outcomes achieved. Quantify impact whenever possible.

• Highlight Collaboration: Demonstrate how you worked with cross-functional teams. Show examples of user flows, wireframes, prototypes, and final UI.

• Emphasize Data: Show how you used research, analytics, or experimentation to inform your design choices and how your designs drove business results.

• Prepare for Questions: Be ready to discuss your design philosophy, your approach to challenging design problems, and how you handle feedback.

Challenge Preparation:

• Understand Jerry's Business: Research Jerry.ai's mission, products, target audience, and competitive landscape. Understand the core problems they are solving in car ownership.

• Focus on Simplification: Given the emphasis on simplifying complex data, anticipate design challenges that require you to translate intricate information into intuitive user experiences.

• AI Application: Consider how AI can be applied to enhance user experience in the context of car ownership.

• Show Your Process: Whether it's a take-home or live exercise, clearly articulate your thought process, assumptions, and design decisions.

📝 Enhancement Note: The interview process described is typical for senior design roles in tech, emphasizing a thorough evaluation of both technical skills and collaborative/strategic capabilities. The advice for portfolio and challenge preparation is tailored to highlight the specific requirements of this role, particularly the emphasis on data, simplification, and AI.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: This is explicitly mentioned as a required skill and will be the primary tool for UI design, prototyping, and collaboration.

• Rapid Prototyping Tools: Candidates should be proficient in tools that allow for quick iteration and demonstration of interactive user flows.

• Design System Tools: Familiarity with tools or methodologies for managing and contributing to design systems.

Analytics & Reporting:

• Product Analytics Platforms: Experience with tools like Amplitude, Mixpanel, or similar platforms for tracking user behavior, engagement, and conversion funnels is highly beneficial.

• A/B Testing Tools: Familiarity with platforms for designing and analyzing A/B tests to validate design hypotheses.

CRM & Automation:

• While not explicitly mentioned for designers, understanding how CRM systems (like Salesforce) and marketing automation tools impact user journeys can be beneficial for context. However, the focus here is on design tools and analytics.

• Data Visualization Tools: Proficiency in tools that can help in understanding and presenting data insights to inform design.

📝 Enhancement Note: The emphasis on Figma and rapid prototyping is standard for UX/UI roles. The inclusion of analytics and A/B testing tools is critical for this role, directly aligning with the "data-informed decision making" requirement and highlighting the operational aspect of measuring design impact.

👥 Team Culture & Values

Operations Values:

• Data-Driven: Decisions are informed by user research, analytics, and experimentation, aiming for measurable impact.

• User-Centric: A strong focus on understanding and solving user problems to make car ownership effortless and enjoyable.

• Efficiency & Simplicity: A drive to simplify complex processes and create intuitive user experiences.

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

• Innovation: Leveraging AI and technology to redefine a traditional industry.

Collaboration Style:

• Cross-Functional Integration: Designers work hand-in-hand with Product Managers, Engineers, and Data Scientists, fostering a highly integrated product development process.

• Iterative Feedback: An environment where design work is regularly shared, critiqued, and refined based on feedback from peers and stakeholders.

• Data-Informed Dialogue: Discussions about design choices are often grounded in data and user insights, leading to productive and objective problem-solving.

📝 Enhancement Note: The company culture appears to be a blend of high-growth tech startup dynamism with a mature focus on data, user experience, and operational efficiency. The values align with a results-oriented environment where design is seen as a critical driver of business success.

⚡ Challenges & Growth Opportunities

Challenges:

• Simplifying Complexity: The primary challenge will be translating the intricate world of car ownership (insurance, financing, maintenance, repairs) and vast amounts of data into a simple, seamless user experience.

• Balancing Craft and Speed: As a growth-stage company, designers will need to maintain high design quality while iterating quickly to meet business objectives.

• Evolving Design System: Contributing to and scaling a design system for a growing product suite requires careful planning and execution to ensure consistency and efficiency.

• AI Integration: Thoughtfully applying AI to enhance user experience without creating complexity or alienating users.

Learning & Development Opportunities:

• Advanced UX/UI: Opportunities to hone skills in complex problem-solving, data visualization, and interaction design.

• AI in Design: Gaining hands-on experience applying AI/ML to product design challenges.

• Industry Expertise: Deepening knowledge in insurtech, fintech, and the automotive market.

• Mentorship: Learning from experienced design leadership and contributing to building a strong design culture.

📝 Enhancement Note: The challenges are directly tied to the nature of the product and the company's growth phase. The opportunities for learning and development are substantial, particularly for a designer looking to expand their skillset in cutting-edge areas like AI and data-driven design within a high-impact industry.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to simplify a complex, data-heavy experience for users. What was your process, and what was the outcome?" (Focus on process, data usage, and measurable impact).

• "How would you approach designing a new feature for Jerry that leverages AI to personalize recommendations for car maintenance?" (Focus on user needs, AI application, and potential UX challenges).

Company & Culture Questions:

• "What interests you about Jerry's mission to simplify car ownership, and how do you see design playing a role in that?" (Showcase understanding of the business and your passion for the problem space).

• "How do you typically collaborate with Product Managers and Engineers? Describe a situation where you had a disagreement and how you resolved it." (Assess collaboration style and conflict resolution).

Portfolio Presentation Strategy:

• Structure: Organize your presentation logically, starting with the business problem or user need, detailing your process, showcasing your solutions (wireframes, prototypes, UI), and concluding with the impact and learnings.

• Quantify Impact: Use metrics whenever possible to demonstrate the success of your designs (e.g., increased conversion, improved engagement, reduced task time).

• Articulate Rationale: Be prepared to explain why you made specific design decisions, linking them back to user needs, business goals, or data insights.

• Showcase Collaboration: Briefly mention how you worked with other team members throughout the project.

📝 Enhancement Note: Preparing for these types of questions will require candidates to thoroughly review their portfolio and practice articulating their design process and impact. Understanding Jerry's business context and its operational focus on data and simplification will be key to providing compelling answers.

📌 Application Steps

To apply for this Sr. Product Designer position:

• Submit your application through the provided link on Ashby.

• Portfolio Customization: Tailor your portfolio to highlight projects that demonstrate your ability to simplify complex data into intuitive user experiences, your data-informed design process, and your experience with consumer-facing mobile or web products.

• Resume Optimization: Ensure your resume clearly outlines your 5+ years of experience, proficiency in Figma, expertise in UX/UI design, and any relevant industry experience (fintech, insurance, mobility). Use keywords from the job description.

• Interview Preparation: Practice articulating your design process, rationale, and the impact of your work. Be ready to present your portfolio and discuss your approach to design challenges, particularly those involving data simplification and AI.

• Company Research: Thoroughly research Jerry.ai's mission, products, target audience, and recent news. Understand their business model and how design contributes to their growth and operational goals.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.