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: 2026-06-22

Experience Level: 5+ Years

Remote Status: Remote OK

🚀 Role Summary

• Drive the end-to-end design process for Jerry's core AI-powered car ownership products, focusing on simplifying complex, data-heavy user experiences.

• Translate user needs, data insights, and business requirements into intuitive user flows, wireframes, prototypes, and high-fidelity UI designs for both mobile and web platforms.

• Collaborate closely with Product Managers, Engineers, and Data Scientists to define user problems, design elegant solutions, and drive measurable business outcomes.

• Contribute to the evolution and consistency of Jerry's design system, ensuring a cohesive and scalable user experience across all touchpoints.

• Thoughtfully integrate AI capabilities to enhance user clarity, personalization, and automation within the car ownership journey.

📝 Enhancement Note: This role is positioned as a "Sr. Product Designer," indicating a need for significant autonomy, strategic input, and the ability to mentor or guide junior team members. The focus on "end-to-end design" and "owning design" suggests a comprehensive responsibility for the product lifecycle from ideation to implementation. The emphasis on AI integration highlights a forward-thinking approach to product development within the automotive and fintech sectors.

📈 Primary Responsibilities

• Partner with Product Managers and Engineering teams to deeply understand user problems, analyze data, and define product scope, translating these into elegant and effective design solutions.

• Lead the creation of comprehensive design artifacts, including user flows, low-fidelity wireframes, interactive prototypes, and polished high-fidelity UIs for new features and existing product enhancements.

• Conduct UX explorations for complex challenges, designing structured workflows that make car ownership, insurance, maintenance, and repairs feel simple, intuitive, and even enjoyable.

• Leverage user research methodologies, data analytics, and A/B testing results to inform design decisions, validate hypotheses, and iteratively improve the user experience.

• Collaborate with other designers to maintain and evolve the company's design system, ensuring visual consistency, scalability, and efficiency across all digital products.

• Strategically apply AI technologies to enhance user experience by improving clarity, delivering personalized recommendations, and automating routine tasks within the car ownership lifecycle.

• Champion user-centric design principles and best practices throughout the product development process, acting as a key advocate for the end-user.

• Present design concepts and rationale clearly and persuasively to cross-functional stakeholders, including executive leadership, engineering, and product management.

📝 Enhancement Note: Based on the "Sr." title and the comprehensive list of responsibilities, this role expects the candidate to not only execute design tasks but also to lead design initiatives, influence product strategy, and contribute to the overall design culture and methodology. The emphasis on "measurable outcomes" and "data-informed decision making" points towards a performance-oriented design approach.

🎓 Skills & Qualifications

Education: A Bachelor's degree in Design, Human-Computer Interaction, Computer Science, or a related field is often preferred for senior roles, but a strong portfolio demonstrating equivalent practical experience is highly valued.

Experience: 5+ years of professional experience in designing consumer-facing mobile or web products, gained through in-house roles or agency work.

Required Skills:

• A strong portfolio showcasing robust UX thinking, data-informed design decision-making processes, and the creation of clean, intuitive, and visually appealing interfaces.

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

• Demonstrated experience in collaborating effectively with Product Managers and Engineers to define product scope, prioritize design solutions, and iterate rapidly on features.

• Proficiency in Figma for UI design, wireframing, prototyping, and collaboration.

• Experience with rapid prototyping tools to effectively communicate design concepts and user interactions.

• Solid understanding of design systems, including their creation, maintenance, and application for ensuring consistency and scalability.

• Excellent communication and presentation skills, with the ability to articulate design rationale clearly and persuasively to both technical and non-technical audiences. Preferred Skills:

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

• Familiarity with user research methodologies and a proven track record of using research insights to drive design decisions.

• Experience with analytics tools to measure design impact and identify areas for improvement.

• Understanding of AI principles and their application in user experience design.

• Experience contributing to or leading the development of a design system.

📝 Enhancement Note: The requirement for a portfolio that "showcases strong UX thinking, data-informed decision making, and clean, intuitive interface design" indicates a high bar for design quality and a focus on measurable impact. The explicit mention of Figma and rapid prototyping highlights essential technical proficiencies. The preference for industry-specific experience suggests that candidates with domain knowledge in marketplaces, fintech, insurance, or mobility will have a competitive edge.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase a minimum of 2-3 comprehensive case studies demonstrating end-to-end product design ownership for consumer-facing mobile or web applications.

• Clearly articulate the problem statement, target audience, and business objectives for each project.

• Detail your specific role and contributions within each project, especially highlighting your UX thinking and data-informed decision-making processes.

• Present a clear progression from initial research and ideation through wireframing, prototyping, UI design, and final implementation.

• Include high-fidelity mockups and interactive prototypes that demonstrate clean, intuitive interface design.

• Quantify the impact of your designs with relevant metrics (e.g., conversion rate improvements, user satisfaction scores, task completion rates, reduction in support tickets). Process Documentation:

• For each case study, outline the design process followed, including user research methods, ideation techniques, and iteration strategies.

• Demonstrate how data analytics and user feedback were integrated into the design process to inform decisions and validate solutions.

• Explain how the design system was utilized or contributed to, ensuring consistency and scalability.

• Detail any collaboration processes with Product Managers and Engineers, highlighting how scope was defined and solutions were iterated upon.

📝 Enhancement Note: The emphasis on a portfolio that includes "data-informed decision making" and "measurable outcomes" is critical. Candidates should be prepared to present not just visually appealing designs but also the strategic thinking and data analysis that underpinned them, demonstrating a clear ROI for their design contributions.

💵 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.

• Potential for equity grants.

Working Hours: 40 hours per week, with flexibility expected to meet project deadlines and collaborate effectively across time zones.

📝 Enhancement Note: The provided salary range of $150,000-$200,000 USD aligns with senior-level product designer roles in the high-cost-of-living Bay Area, especially for a well-funded, high-growth tech company like Jerry.ai. The inclusion of equity grants suggests that total compensation could exceed the base salary range, offering significant upside potential. The benefits package is competitive and standard for full-time roles at established tech companies.

🎯 Team & Company Context

🏢 Company Culture

Industry: Jerry.ai operates within the Automotive, Fintech, and Insurtech sectors, aiming to disrupt the $2T car ownership market. The company leverages AI and machine learning to create a seamless, end-to-end experience for car owners.

Company Size: Jerry.ai has grown significantly, indicated by its funding of $240M and its aim to become a $10B company. The product org alone comprises 11 PMs, 55 engineers, and 12 analysts/data scientists, suggesting a mid-to-large size company with a substantial engineering and product footprint.

Founded: Founded in 2017, Jerry.ai has established itself as a leader in its category, reaching profitability in 2024. This maturity indicates a stable yet rapidly growing organization with a clear product-market fit and a strategic vision for scale.

Team Structure:

• The design team, led by Kruise Sapstein (Head of Design), is focused on building a "high-performing, high-craft design culture."

• The Senior Product Designer will work within a broader product organization that includes Product Managers (11), Engineers (55), and Analysts/Data Scientists (12), fostering cross-functional collaboration.

• The reporting structure places the designer under the Head of Design, with direct collaboration lines to Product leadership (CEO & Head of Product) and day-to-day work with PMs and engineers. Methodology:

• Data-Driven Design: The team utilizes research, analytics, and experimentation to inform design decisions, emphasizing measurable outcomes.

• Agile Development: The mention of rapid iteration and close collaboration with engineers suggests an agile or lean development methodology.

• AI Integration: A core part of the company's strategy is to apply AI/ML to enhance user experience, personalize services, and automate processes.

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

📝 Enhancement Note: Jerry.ai presents itself as a rapidly growing, well-funded startup that has achieved profitability and aims for significant market disruption. The culture appears to value high craft, data-driven decision-making, and collaborative innovation, particularly in applying AI to a traditionally analog industry. The emphasis on "no cog in a big design machine" suggests a culture that values individual impact and direct contribution to product strategy.

📈 Career & Growth Analysis

Operations Career Level: This role is classified as a Senior Product Designer, indicating a mid-to-senior level position. It requires significant experience, autonomy, and the ability to influence product direction. The responsibilities span end-to-end design ownership, strategic problem-solving, and contributing to the design system, suggesting a role that goes beyond execution to include strategic input and mentorship.

Reporting Structure: The Senior Product Designer will report directly to the Head of Design, Kruise Sapstein. They will also work closely with Art Agrawal (CEO & Head of Product) and collaborate daily with Product Managers, Engineers, and Data Scientists. This structure allows for high visibility and direct impact on product strategy and execution.

Operations Impact: The Senior Product Designer's work will directly shape how millions of users interact with Jerry's core products. By simplifying complex data and creating intuitive experiences for car ownership, insurance, maintenance, and repairs, the designer will play a crucial role in driving user adoption, satisfaction, and retention, ultimately contributing to the company's growth and business objectives. The focus on "measurable outcomes" underscores the expectation that design directly impacts key performance indicators.

Growth Opportunities:

• Design Leadership: Potential to grow into a Lead Product Designer or Design Manager role as the design team expands, with opportunities to mentor junior designers and shape design strategy.

• Specialization: Deepen expertise in designing for complex, data-rich domains, AI-powered experiences, or specific areas within car ownership (e.g., insurance, maintenance, finance).

• Cross-Functional Influence: Develop stronger strategic partnerships with Product and Engineering, potentially leading design initiatives for major product launches or strategic pivots.

• Industry Expertise: Gain deep knowledge in the rapidly evolving Insurtech, Fintech, and Mobility sectors.

📝 Enhancement Note: The "Sr." title and reporting structure indicate a role with significant influence and growth potential. The company's ambitious growth targets and focus on innovation suggest ample opportunities for career advancement and skill development within a dynamic environment.

🌐 Work Environment

Office Type: While the job posting indicates "TELECOMMUTE" and lists multiple potential remote locations, Jerry.ai also has a physical headquarters in Palo Alto, California, and potentially other offices. The company's approach to work seems flexible, supporting remote work while maintaining a physical presence for collaboration.

Office Location(s):

• Primary HQ: Palo Alto, California, United States.

• Supported Remote Locations (Derived): Palo Alto, CA; Austin, TX; Chicago, IL; Los Angeles, CA; Phoenix, AZ; Portland, OR.

• Potential for Bay Area presence (San Francisco Bay Area, California, United States) is also indicated. Workspace Context:

• Remote Flexibility: The role is suitable for remote candidates within the United States, offering flexibility in where the designer works.

• Collaborative Environment: Despite remote options, the emphasis on collaboration with PMs, engineers, and data scientists suggests a culture that values teamwork and communication, likely facilitated through digital tools.

• Tooling: Expect access to standard design and collaboration tools (Figma, prototyping tools, Slack, etc.) necessary for effective remote and cross-functional work.

Work Schedule: The standard working hours are 40 hours per week. Given the remote nature and cross-functional collaboration, flexibility in scheduling to accommodate meetings across different time zones (e.g., PST, CST, EST) will be important.

📝 Enhancement Note: The "TELECOMMUTE" designation and the list of supported remote locations confirm that this role is primarily remote. However, candidates should be aware of the company's headquarters and potential for hybrid work arrangements or in-person collaboration opportunities, especially if located near a Jerry.ai office.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio to assess qualifications and fit for the role.

• Portfolio Presentation & Discussion: An interview where you'll present 1-2 of your strongest case studies, detailing your process, decisions, and outcomes. Expect deep dives into your UX thinking, data usage, and problem-solving approach.

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

• Hiring Manager Interview: A discussion with Kruise Sapstein (Head of Design) to delve into your experience, design philosophy, and how you contribute to a high-craft design culture.

• Executive Interview (Potential): Depending on the stage, you might meet with Art Agrawal (CEO & Head of Product) to discuss strategic alignment and overall vision.

Portfolio Review Tips:

• Focus on Impact: Clearly articulate the problem you solved, your design process, and the measurable impact of your solutions. Use data and metrics to support your claims.

• Showcase Process: Go beyond final visuals; explain your thought process, trade-offs considered, and how you arrived at your design decisions.

• Tailor to Jerry.ai: Highlight projects that demonstrate experience with complex data, consumer-facing apps, AI integration, or relevant industries (fintech, insurance, mobility).

• Clarity and Conciseness: Present your work clearly, using well-organized case studies that are easy to follow for both designers and non-designers.

• Figma & Prototyping: Be ready to demonstrate your proficiency in Figma and discuss your prototyping approach.

Challenge Preparation:

• Be prepared for a design challenge, which might involve solving a hypothetical problem related to Jerry's product or a similar domain.

• Practice articulating your design process under time constraints and presenting your rationale persuasively.

• Think about how you would approach understanding user needs, defining problems, exploring solutions, and iterating based on data and feedback.

📝 Enhancement Note: The emphasis on portfolio presentation and case studies suggests that this is a critical component of the interview process. Candidates should be ready to present detailed, data-backed examples of their work that align with Jerry.ai's focus on simplifying complex experiences through design and AI.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Essential for UI design, wireframing, prototyping, and collaborative design workflows. Proficiency is a core requirement.

• Prototyping Tools: Experience with rapid prototyping tools beyond Figma (e.g., InVision, ProtoPie) may be beneficial for communicating complex interactions.

Analytics & Reporting:

• Data Analysis Tools: Experience using data from analytics platforms (e.g., Mixpanel, Amplitude, Google Analytics) to inform design decisions and measure impact is highly valued.

• A/B Testing Platforms: Understanding how to design for and interpret results from A/B tests is crucial for data-informed iteration.

CRM & Automation:

• While not explicitly listed for the designer role, familiarity with how CRM systems (e.g., Salesforce) and automation platforms integrate with user-facing products can provide valuable context for designing seamless customer journeys.

📝 Enhancement Note: Figma is explicitly called out as a required skill. The role also necessitates a strong understanding of how to leverage data and analytics tools to inform design decisions and measure success, indicating a data-driven design approach.

👥 Team Culture & Values

Operations Values:

• High Craft: A strong emphasis on the quality, polish, and thoughtful execution of design work.

• Data-Informed Decision Making: Designs are grounded in research, analytics, and experimentation, not just intuition.

• Collaboration: Working closely and effectively with Product Managers, Engineers, and Data Scientists to achieve shared goals.

• User-Centricity: A commitment to understanding and solving real user problems to make car ownership effortless.

• Innovation: Embracing AI and new technologies to redefine the car ownership experience.

• Egoless Approach: A collaborative mindset focused on the best solution for the product and users, rather than personal preference.

Collaboration Style:

• Cross-Functional Integration: The design team works hand-in-hand with product and engineering to ensure designs are feasible, impactful, and well-implemented.

• Feedback Loops: An open culture for giving and receiving constructive feedback to continuously improve designs and processes.

• Agile & Iterative: A dynamic approach to product development where designs are iterated upon based on feedback and data.

📝 Enhancement Note: The description highlights a culture that values both high-quality design execution ("high craft") and rigorous, data-backed decision-making. The "egoless" aspect suggests a team that prioritizes collective success and constructive problem-solving.

⚡ Challenges & Growth Opportunities

Challenges:

• Simplifying Complexity: Translating the highly complex and often frustrating aspects of car ownership (insurance, financing, repairs) into simple, intuitive digital experiences.

• Balancing Data and Intuition: Effectively using quantitative data while also relying on UX best practices and creative problem-solving.

• Evolving Design System: Maintaining and scaling a design system across a growing product suite and team.

• AI Integration: Designing user experiences that effectively leverage AI to provide genuine value without being intrusive or overly technical.

Learning & Development Opportunities:

• Advanced UX/UI Skills: Opportunities to refine skills in complex problem-solving, data visualization, and AI-driven design.

• Industry Expertise: Deep dive into the automotive, fintech, and insurtech sectors, understanding unique user needs and market dynamics.

• Cross-Functional Acumen: Enhance skills in collaborating with data scientists and engineers to build technically sophisticated and user-friendly products.

• Leadership Potential: Develop leadership qualities through mentorship, design system contributions, and strategic input into product roadmaps.

📝 Enhancement Note: The challenges presented are inherent to Jerry.ai's mission and the nature of the industries it operates within. The growth opportunities are tied to developing specialized skills and leadership capabilities within a rapidly evolving tech landscape.

💡 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 UX thinking, process, and data-informed decision making).

• "How do you balance user needs with business objectives and technical constraints when designing a new feature?" (Focus on collaboration, trade-offs, and strategic thinking).

• "Walk me through a project where you significantly influenced the product roadmap or strategy through your design work." (Focus on impact, communication, and leadership). Company & Culture Questions:

• "Why are you interested in Jerry.ai and our mission to simplify car ownership?" (Research Jerry's product, mission, and recent achievements).

• "How do you contribute to a 'high-craft' design culture?" (Discuss your approach to design quality, mentorship, and raising design standards).

• "Describe your experience working within an 'egoless' team environment." (Highlight your collaborative approach and focus on collective success). Portfolio Presentation Strategy:

• Structure: For each case study, clearly present the problem, your role, your process (research, ideation, design, testing), key design decisions, and measurable results.

• Storytelling: Weave a narrative that highlights the challenges you faced and how your design solutions addressed them effectively.

• Visuals: Use high-fidelity mockups and interactive prototypes to showcase the final product, but don't shy away from showing early-stage wireframes and sketches to illustrate your process.

• Data Emphasis: Quantify the impact of your work with specific metrics and explain how you used data to inform your decisions.

• Be Prepared for Questions: Anticipate questions about your design choices, trade-offs, and how you would approach similar problems at Jerry.ai.

📝 Enhancement Note: Candidates should prepare to demonstrate not only their design skills but also their strategic thinking, collaborative abilities, and understanding of data-driven product development. The interview process will likely probe deeply into their portfolio and past experiences.

📌 Application Steps

To apply for this Sr. Product Designer position:

• Submit your resume and a link to your online portfolio through the Ashby application portal.

• Portfolio Customization: Ensure your portfolio prominently features 2-3 detailed case studies that showcase your end-to-end design process, strong UX thinking, data-informed decision-making, and measurable impact. Tailor the case study selection to highlight experiences relevant to Jerry.ai's mission (simplifying complex consumer products, AI integration, fintech/insurtech).

• Resume Optimization: Highlight your 5+ years of experience in consumer-facing product design, proficiency in Figma and prototyping, and any relevant industry experience (marketplaces, fintech, insurance, mobility). Quantify achievements where possible.

• Interview Preparation: Practice presenting your case studies clearly and concisely, focusing on your process, rationale, and the data-driven outcomes. Prepare to discuss your approach to collaborative design and contributing to a high-craft culture.

• Company Research: Thoroughly research Jerry.ai's product, mission, recent news, and market position. Understand their use of AI and their goal of simplifying car ownership. Be prepared to articulate why you are a good fit for their specific culture and challenges.

⚠️ 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.