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 25, 2026

Experience Level: 5+ Years

Remote Status: Remote OK (United States)

🚀 Role Summary

• Lead end-to-end product design for Jerry's core AI-powered car ownership platform, focusing on intuitive and user-friendly experiences.

• Translate complex data and user needs into elegant, scalable design solutions across mobile and web platforms.

• Collaborate closely with product management, engineering, and data science teams to drive product strategy and deliver measurable business outcomes.

• Contribute to the evolution of Jerry's design system and uphold a high standard of design craft.

📝 Enhancement Note: This role is positioned as a Senior Product Designer, indicating a need for significant autonomy, strategic input, and the ability to mentor or influence other designers. The emphasis on AI and a "super app" for car ownership suggests a complex, data-rich environment where design plays a critical role in simplifying user interactions and driving adoption. The company's profitability and growth trajectory signal a stable and expanding organization.

📈 Primary Responsibilities

• Partner with Product Managers and Engineers to deeply understand user problems, define product requirements, and design intuitive solutions that address complex, data-heavy experiences.

• Own the creation of comprehensive design artifacts, including user flows, low-fidelity wireframes, high-fidelity mockups, and interactive prototypes for new features and product enhancements across mobile and web applications.

• Drive UX exploration for challenging problems, structuring complex workflows to ensure car ownership and management feel simple, effortless, and even enjoyable for millions of users.

• Leverage user research, quantitative analytics, and A/B testing insights to inform design decisions, validate proposed solutions, and iterate towards optimal user experiences.

• Actively contribute to and help evolve Jerry's centralized design system, ensuring visual consistency, scalability, and efficiency across all product touchpoints.

• Thoughtfully integrate AI capabilities into the user experience to enhance clarity, deliver personalized insights, and introduce intelligent automation.

• Collaborate with a cross-functional team including Product Managers, Engineers, Data Scientists, and fellow designers to ensure successful product development and launch.

📝 Enhancement Note: The responsibilities highlight a full-stack design role, requiring not just visual design but also strong UX strategy, problem-solving, and a data-informed approach. The emphasis on "simplifying data-heavy experiences" and "applying AI" suggests a unique challenge requiring sophisticated design thinking. The mention of "measurable outcomes" implies a need to connect design work directly to business KPIs.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio demonstrating relevant skills and experience is paramount. A background in Design, Human-Computer Interaction (HCI), or a related field is often beneficial.

Experience: 5+ years of professional experience designing consumer-facing mobile or web products, with a proven track record of delivering impactful design solutions. Agency or in-house experience is acceptable.

Required Skills:

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

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

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

• Experience with rapid prototyping tools to effectively communicate design concepts and gather feedback.

• Solid understanding of design systems: their principles, implementation, and evolution for maintaining consistency and scalability across products.

• Excellent verbal and written communication skills, with the ability to articulate design rationale clearly and persuasively to both technical and non-technical stakeholders.

Preferred Skills:

• Experience designing within marketplaces, fintech, insurance, or mobility-related industries.

• Familiarity with user research methodologies and data analysis tools to inform design strategies.

• Experience applying AI/ML concepts to product design challenges.

• Understanding of front-end development principles to foster better collaboration with engineering teams.

📝 Enhancement Note: The "bonus" skills are significant for this role given Jerry's industry. Candidates with experience in marketplaces, fintech, or insurance will have a direct advantage due to the complexity and specific user needs within these domains. The emphasis on AI application is also a key differentiator.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrate a clear process for problem identification, user research, and ideation.

• Showcase case studies with a strong emphasis on user-centered design principles and how user needs were translated into functional designs.

• Include examples of complex data visualization or simplification challenges and how design addressed them.

• Present high-fidelity mockups and interactive prototypes that illustrate intuitive user flows and polished UI design.

Process Documentation:

• For each case study, detail the design process followed, from initial concept and user flows to wireframes, UI design, and prototyping.

• Explain how data, analytics, and user research informed your design decisions at each stage.

• Illustrate how you collaborated with product managers and engineers throughout the design and development lifecycle.

• Show examples of how you have contributed to or utilized design systems for consistency and efficiency.

📝 Enhancement Note: A strong portfolio is critical for this role. Candidates should prepare to walk through 2-3 detailed case studies that highlight their problem-solving approach, design process, collaboration skills, and the measurable impact of their work. The focus should be on complexity and data-informed solutions.

💵 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.

• Opportunities for equity grants and/or stock options.

Working Hours: Standard full-time hours, typically 40 hours per week, with flexibility expected for a remote role and to meet project deadlines.

📝 Enhancement Note: The salary range is competitive for a Senior Product Designer role in the Palo Alto/Bay Area market, even for a remote position. The inclusion of equity grants/stock options is a significant part of the total compensation package for this level of role at a growth-stage tech company. The mention of "regular employees" implies that benefits may vary for contract or freelance roles, which is typical.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, specifically focused on Automotive, Insurance, Fintech, and AI-driven Consumer Services. Jerry.ai operates within a massive $2T industry, aiming to disrupt traditional car ownership models.

Company Size: Jerry.ai has grown significantly, with a product organization of 11 PMs, 55 engineers, and 12 analysts/data scientists. This indicates a mid-sized, agile tech company with substantial engineering and product talent.

Founded: Founded in 2017, Jerry.ai has a history of innovation and has achieved profitability, backed by substantial funding ($240M), positioning it as a stable yet rapidly growing entity.

Team Structure:

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

• The Senior Product Designer will report into this design leadership structure.

Methodology:

• The company emphasizes a data-driven approach to product development, utilizing research, analytics, and experimentation to inform design decisions.

• Workflow planning and optimization are key, with a focus on simplifying complex processes for car ownership.

• Automation and efficiency are core tenets, particularly through the application of AI.

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

📝 Enhancement Note: Jerry.ai positions itself as a disruptive force in a large, traditional industry. The culture appears to be fast-paced, data-centric, and focused on building a high-quality, consumer-friendly product. The mention of "passionate, curious and egoless people" suggests a collaborative and growth-oriented environment.

📈 Career & Growth Analysis

Operations Career Level: This is a Senior Product Designer role, indicating an individual contributor position with significant scope and responsibility. It implies the ability to take ownership of complex projects, contribute strategically to product direction, and potentially mentor junior designers.

Reporting Structure: The role reports to the Head of Design, Kruise Sapstein, and collaborates extensively with Product Managers, Engineers, and Data Scientists. This structure allows for direct mentorship and visibility at a leadership level.

Operations Impact: The designer's work will directly influence how millions of users manage their car ownership experience, impacting key business metrics such as customer acquisition, retention, engagement, and satisfaction. The goal is to make car ownership feel effortless, which is a significant value proposition.

Growth Opportunities:

• Deepening AI Design Expertise: Opportunity to become a leader in designing AI-powered consumer experiences within the automotive/fintech space.

• Design System Leadership: Potential to take on more responsibility in evolving and scaling the design system as the company grows.

• Product Strategy Influence: As a senior member, contribute more significantly to product strategy and roadmap through design insights and innovation.

• Mentorship: Potential to mentor junior designers and contribute to building a strong design team culture.

• Career Advancement: Path to Lead Product Designer or Design Manager roles as the design team expands.

📝 Enhancement Note: This role offers a clear path for growth within a rapidly expanding company. The opportunity to shape a product in a massive market with a focus on AI is a significant career development prospect for a product designer.

🌐 Work Environment

Office Type: While the job posting lists "TELECOMMUTE" and "Remote OK" with multiple US locations, the headquarters are in Palo Alto, California. This suggests a strong remote-first or hybrid-flexible culture, with an emphasis on collaboration tools and asynchronous communication.

Office Location(s): Jerry.ai has a presence in Palo Alto, CA, and is open to remote employees across the US, including Austin, TX; Chicago, IL; Los Angeles, CA; Phoenix, AZ; Portland, OR; and the San Francisco Bay Area.

Workspace Context:

• The remote-first nature necessitates strong digital collaboration tools and practices.

• Designers will have access to a robust tech stack and work within a highly cross-functional environment.

• Opportunities for interaction will be through virtual meetings, Slack, and collaborative design platforms.

Work Schedule: The role is full-time, with standard working hours. Flexibility is expected, especially given the remote nature and the need to collaborate across different time zones if applicable. The emphasis on asynchronous communication supports this flexibility.

📝 Enhancement Note: The remote flexibility is a key aspect of this role, offering work-life balance and the ability to work from various locations within the US. The company's infrastructure and culture should support effective remote collaboration.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter will review applications and portfolios for alignment with the core requirements.

• Portfolio Presentation & Design Challenge: Candidates will likely present their portfolio, discussing 2-3 key projects in detail, focusing on their process, problem-solving, and impact. A design challenge, either take-home or live, may be administered to assess practical design skills and problem-solving abilities.

• Cross-functional Interviews: Interviews with Product Managers, Engineers, and Data Scientists to assess collaboration, communication, and technical understanding.

• Hiring Manager Interview: A discussion with Kruise Sapstein (Head of Design) to assess cultural fit, design philosophy, and leadership potential.

• Executive/CEO Interview: Potentially an interview with Art Agrawal (CEO & Head of Product) for senior roles to gauge strategic alignment and overall fit.

Portfolio Review Tips:

• Focus on Impact: Quantify your contributions whenever possible. Use metrics, user feedback, or business outcomes to demonstrate the value of your design work.

• Show Your Process: Clearly articulate the "why" behind your design decisions. Detail your research, ideation, iteration, and collaboration steps.

• Highlight Complexity: Showcase projects that involved tackling complex problems, handling large datasets, or simplifying intricate workflows, especially those relevant to AI or data-intensive applications.

• Tailor to Jerry.ai: Emphasize projects that demonstrate experience with consumer-facing products, mobile-first design, and ideally, experience in marketplaces, fintech, or insurance.

• Visual Polish: Ensure your portfolio is well-designed, easy to navigate, and visually appealing, reflecting your attention to detail.

Challenge Preparation:

• Anticipate challenges that require designing for data complexity, AI integration, or simplifying a core car ownership task (e.g., insurance comparison, maintenance scheduling).

• Practice articulating your thought process clearly and concisely, explaining your assumptions, constraints, and design choices.

• Be prepared to discuss how you would use data and user research to validate your design solutions.

📝 Enhancement Note: The interview process is likely rigorous, focusing on both design craft and strategic thinking. A strong portfolio presentation is paramount, acting as the primary tool for demonstrating capabilities. Candidates should prepare to articulate their value proposition in the context of Jerry's mission.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The core tool for UI design, wireframing, and prototyping. Proficiency is essential.

• Prototyping Tools: Beyond Figma's capabilities, experience with tools like InVision, ProtoPie, or similar for more advanced interactions.

Analytics & Reporting:

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

CRM & Automation:

• While not directly a design tool, understanding how CRM systems (like Salesforce, HubSpot) and automation platforms integrate with user-facing products can be beneficial for context.

📝 Enhancement Note: Figma is explicitly mentioned, making it a non-negotiable skill. Familiarity with analytics tools is crucial given the company's data-driven approach. Understanding the broader ecosystem of product development tools will enhance collaboration.

👥 Team Culture & Values

Operations Values:

• User-Centricity: A strong focus on understanding and serving the needs of car owners, making their lives easier.

• Data-Driven Innovation: Decisions are informed by data, analytics, and user research to ensure effectiveness and impact.

• Craftsmanship: A commitment to high-quality design, intuitive interfaces, and a polished user experience.

• Collaboration: Working effectively across teams (PM, Eng, Data) to achieve common goals.

• Efficiency & Automation: Leveraging technology, particularly AI, to streamline processes and improve user outcomes.

Collaboration Style:

• Cross-functional Partnership: Designers work closely with PMs and Engineers from discovery through launch.

• Iterative Design: A culture of continuous improvement and rapid iteration based on feedback and data.

• Open Communication: Encouraging clear and direct communication via tools like Slack and regular virtual meetings.

• Design System Adoption: Emphasis on using and contributing to the design system for consistency and efficiency.

📝 Enhancement Note: The emphasis on "high-craft design culture" and "egoless people" suggests a team that values both individual excellence and collaborative problem-solving, with a shared commitment to the product's success.

⚡ Challenges & Growth Opportunities

Challenges:

• Simplifying Complexity: Making the multifaceted world of car ownership (insurance, financing, maintenance, repairs) feel simple and accessible through design.

• Data-Heavy Interfaces: Designing experiences that effectively present and leverage large amounts of data without overwhelming the user.

• AI Integration: Thoughtfully applying AI to enhance user experience, ensuring it's helpful, transparent, and not intrusive.

• Scaling Design System: Evolving and maintaining a design system that supports rapid product growth and new feature development.

• Remote Collaboration: Ensuring effective communication and collaboration within a distributed team environment.

Learning & Development Opportunities:

• Specialization in AI/ML Design: Gaining deep expertise in designing for AI-powered consumer applications.

• Industry Expertise: Developing a strong understanding of the automotive, insurance, and fintech sectors.

• Product Strategy Contribution: Opportunity to influence product direction and strategy through design leadership.

• Mentorship: Gaining experience in mentoring junior designers and contributing to team growth.

• Scaling Impact: Working on a product used by millions, offering the chance to see the impact of your designs on a large scale.

📝 Enhancement Note: This role presents significant challenges that also serve as substantial growth opportunities, particularly in the emerging field of AI-driven consumer products and complex data design.

💡 Interview Preparation

Strategy Questions:

• "Tell me about a time you had to simplify a complex, data-heavy user experience. What was your process, and what was the outcome?" (Focus on data simplification, user research, and measurable impact).

• "How would you approach designing a new AI-powered feature for car owners? What considerations would be most important?" (Focus on AI ethics, user trust, transparency, and value proposition).

Company & Culture Questions:

• "What interests you about Jerry.ai's mission to simplify car ownership?" (Show genuine interest in the problem space and company vision).

• "How do you see yourself contributing to Jerry's design culture and evolving our design system?" (Highlight collaboration, mentorship, and design system expertise).

Portfolio Presentation Strategy:

• Structure: For each case study, follow a clear narrative: Problem -> Your Role -> Process -> Solution -> Impact.

• Highlight Data & AI: Explicitly call out how you used data or considered AI in your projects.

• Show Iteration: Demonstrate how you iterated on designs based on feedback or testing.

• Quantify Impact: Whenever possible, use metrics to showcase the success of your designs.

• Engage: Be prepared for in-depth questions about your process and decisions. Treat it as a collaborative discussion.

📝 Enhancement Note: Preparation should focus on demonstrating not just design skill, but also strategic thinking, a data-informed mindset, and strong collaborative capabilities, all tailored to Jerry.ai's unique market and product.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the provided link on Ashby.

• Prepare your portfolio to showcase 2-3 of your strongest, most relevant projects, focusing on end-to-end design process, UX thinking, data-informed decisions, and measurable impact.

• Tailor your resume to highlight experience with consumer-facing products, mobile/web design, Figma, design systems, and any relevant industry experience (fintech, insurance, marketplaces).

• Practice articulating your design process and problem-solving methodologies, preparing to discuss key portfolio projects and potential design challenges.

• Thoroughly research Jerry.ai's mission, product, and recent news to understand their business goals and how design contributes to their strategy.

⚠️ 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.

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