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: 2026-06-08T00:00:00

Experience Level: 5-10 Years

Remote Status: Fully Remote (US-based candidates preferred)

🚀 Role Summary

• Drive the end-to-end design process for Jerry's suite of car ownership products, from initial concept to final UI implementation, ensuring a seamless and intuitive user experience.

• Translate complex data and product requirements into simple, elegant workflows and visually polished interfaces for millions of consumers.

• Collaborate closely with Product Management, Engineering, and Data Science teams to define user problems and design solutions that yield measurable business outcomes.

• Contribute to the evolution and consistency of Jerry's design system across mobile and web platforms, elevating the overall craft and quality of the user interface.

• Leverage user research, analytics, and experimentation to inform design decisions and validate the effectiveness of proposed solutions.

📝 Enhancement Note: This role is positioned as a Senior Product Designer, indicating a need for a candidate with substantial experience (5+ years) capable of independent ownership of design projects and strategic input into product direction. The emphasis on "AI-powered assistant for car ownership" and "reimagining the entire experience" suggests a focus on innovation and user-centric problem-solving within a complex, data-rich domain. The "fully remote" status with a preference for US-based candidates implies a need for strong self-management and communication skills.

📈 Primary Responsibilities

• Partner with Product Managers and Engineers to deeply understand user challenges, simplify data-intensive experiences, and design innovative solutions that lead to tangible improvements in user engagement and business metrics.

• Develop comprehensive user flows, low-fidelity wireframes, high-fidelity mockups, and interactive prototypes to effectively communicate design concepts and user journeys for new features and existing product enhancements.

• Lead UX exploration for intricate problems, conceptualizing and structuring intuitive workflows that demystify car ownership and management tasks for end-users.

• Utilize a data-informed approach, integrating insights from user research, product analytics, and A/B testing to guide design decisions and validate the efficacy of design solutions.

• Actively contribute to the refinement and expansion of the company's design system, ensuring visual consistency, scalability, and efficiency across all digital touchpoints (mobile and web).

• Thoughtfully integrate AI capabilities to enhance user experience through improved clarity, personalization, and automation of car ownership tasks.

• Collaborate with cross-functional teams, including data scientists and analysts, to identify opportunities for design innovation and data-driven product improvements.

📝 Enhancement Note: The responsibilities highlight a hands-on design role with significant strategic influence. The emphasis on "simplify data-heavy experiences" and "thoughtfully apply AI" points to a need for designers who can handle complexity and leverage emerging technologies. The requirement to "lead UX explorations for complex problems" suggests a senior-level individual contributor expected to tackle ambiguous challenges.

🎓 Skills & Qualifications

Education: While not explicitly stated, a Bachelor's degree in Design, Human-Computer Interaction, or a related field is typically expected for this level of seniority. Equivalent practical experience will also be considered.

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

Required Skills:

• A strong portfolio demonstrating exceptional UX thinking, data-informed decision-making processes, and the creation of clean, intuitive interface designs.

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

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

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

• Solid understanding of design systems, with the ability to utilize or contribute to their development for consistency and scalability.

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

• Experience collaborating effectively with Product Managers and Engineers to define scope, prioritize solutions, and iterate rapidly on designs. Preferred Skills:

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

• Familiarity with user research methodologies and their application in design decision-making.

• Experience in leveraging analytics and experimentation data to inform and validate design strategies.

• Understanding of AI/ML principles and their application in enhancing user experiences.

📝 Enhancement Note: The requirements emphasize practical skills and a proven track record, as evidenced by the portfolio requirement. The "5+ years" experience level aligns with a Senior Designer role, expecting autonomy and strategic input. The preferred skills indicate areas where candidates can stand out, particularly in highly relevant industries or with advanced analytical/AI experience.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

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

• Clearly articulate the user problem, the design process undertaken, and the rationale behind key design decisions for each project.

• Include examples of user flows, wireframes, high-fidelity mockups, and interactive prototypes.

• Highlight how data, user research, or analytics informed your design choices and led to measurable outcomes.

• Demonstrate experience in simplifying complex, data-heavy information into intuitive user interfaces.

• Present a strong understanding of UI principles, visual design, and interaction design. Process Documentation:

• For each project presented, detail the steps taken in the design process, including discovery, ideation, iteration, and validation phases.

• Emphasize collaboration with cross-functional partners (PMs, Engineers, Data Scientists) and how feedback was incorporated.

• If applicable, showcase contributions to or utilization of design systems, illustrating how consistency and scalability were maintained.

• Clearly articulate the impact of your design solutions, ideally with quantifiable results (e.g., conversion rate improvements, task completion times, user satisfaction scores).

📝 Enhancement Note: The portfolio is a critical component for this role, serving as the primary evidence of a candidate's design capabilities. The emphasis on "data-informed decision making" and "simplifying complex data" implies a need for case studies that clearly illustrate analytical thinking and problem-solving in data-rich environments. The inclusion of AI application in preferred skills suggests that projects demonstrating innovative use of technology would be highly valued.

💵 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 contributions.

• Wellness benefits.

• Equity grants, potentially including stock options.

Working Hours: The standard working hours are 40 hours per week, with flexibility expected to meet project deadlines and collaborative needs.

📝 Enhancement Note: The salary range provided is competitive for a Senior Product Designer role in the San Francisco Bay Area, reflecting the high cost of living and the demand for experienced design talent. The inclusion of equity grants and stock options suggests a growth-oriented company where employees can benefit from the company's success. The "fully remote" status for US-based candidates indicates flexibility, but a 40-hour work week is standard.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, specifically focusing on Automotive Services, Fintech, and AI-powered Consumer Applications. Jerry.ai operates in the massive $2T car ownership industry, aiming to disrupt traditional, analog, and friction-filled processes.

Company Size: Jerry.ai has grown significantly, indicated by their backing of $240M in funding and ambitious $10B company valuation target by 2030. The product organization alone comprises 11 PMs, 55 engineers, and 12 analysts/data scientists, suggesting a substantial and well-resourced team.

Founded: Founded in 2017, Jerry.ai has a track record of innovation and growth, reaching profitability in 2024.

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.

• Designers will collaborate directly with Product Managers (11), Engineers (55), and Analysts/Data Scientists (12), indicating a highly cross-functional and data-driven product development environment.

• The CEO, Art Agrawal, is also Head of Product, emphasizing a strong commitment to product vision and customer experience from the top. Methodology:

• Design decisions are informed by research, analytics, and experimentation, reflecting a data-driven approach to product development.

• The company emphasizes translating complex data into simple, intuitive experiences, suggesting a focus on user-centric design principles and clear information architecture.

• AI is a core component of Jerry's strategy, indicating an expectation for designers to explore and apply AI to enhance user clarity, personalization, and automation.

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

📝 Enhancement Note: Jerry.ai presents itself as a rapidly growing, well-funded tech company with a clear mission to simplify car ownership through AI. The culture appears to be collaborative, data-driven, and focused on innovation within a traditionally complex industry. The direct involvement of the CEO in product strategy underscores the importance of product and design.

📈 Career & Growth Analysis

Operations Career Level: This role is designated as "Sr. Product Designer," signifying an experienced individual contributor expected to operate with a high degree of autonomy. The scope includes end-to-end design ownership, leading UX explorations for complex problems, and contributing to strategic product decisions. This level typically involves mentoring junior designers and influencing design best practices.

Reporting Structure: The Senior Product Designer will report to the Head of Design, Kruise Sapstein. They will also work closely with Product Managers, Engineers, and Data Scientists, fostering a collaborative cross-functional environment.

Operations Impact: The impact of this role is significant, as design is positioned as the primary mechanism for making car ownership "easy and even enjoyable." The designer's work will directly influence how millions of people interact with Jerry's core products, impacting user satisfaction, retention, and the company's overall growth trajectory towards its $10B valuation goal. Design solutions are expected to drive "measurable outcomes."

Growth Opportunities:

• Skill Advancement: Opportunities to deepen expertise in UX/UI design for complex, data-rich applications, AI-driven product design, and evolving design systems. Potential to lead design initiatives for major product features.

• Leadership Potential: As a senior member, there's potential to mentor junior designers, contribute to hiring, and take on lead roles for specific product areas or design challenges.

• Industry Exposure: Gaining experience in the rapidly evolving automotive services, fintech, and AI sectors, contributing to a company poised for significant growth and market disruption.

• Strategic Influence: Direct collaboration with C-suite and senior leadership provides visibility into product strategy and business decision-making.

📝 Enhancement Note: The "Sr. Product Designer" title implies career progression beyond a standard designer role, with opportunities for leadership and strategic impact. The company's ambitious growth plans suggest a dynamic environment where a designer can make a significant contribution and potentially grow with the company.

🌐 Work Environment

Office Type: The company operates a distributed, remote-first model for its US-based employees. While the headquarters is in Palo Alto, the job is advertised as "TELECOMMUTE" and "Fully Remote," indicating a preference for remote work.

Office Location(s): While Jerry.ai is headquartered in Palo Alto, California, the job posting specifies remote work for US-based candidates. The provided "ai_remote_location_derived" list (Palo Alto, Austin, Chicago, Los Angeles, Phoenix, Portland) suggests that while remote, there might be a preference for candidates in or near these tech hubs, potentially for occasional in-person collaboration or team events.

Workspace Context:

• Expect a highly collaborative environment, even remotely, with frequent interactions via video calls, Slack, and project management tools.

• Access to modern design tools (Figma) and potentially other collaboration software will be provided.

• The emphasis on "high-craft design culture" suggests an environment that values quality, attention to detail, and thoughtful design execution.

• Opportunities for cross-functional collaboration with engineers, PMs, and data scientists will be frequent, requiring strong virtual communication and teamwork skills.

Work Schedule: The standard work schedule is 40 hours per week. While remote, maintaining consistent communication and availability during core business hours (likely Pacific Time, given the HQ and common tech industry practices) will be important for effective collaboration. Flexibility may be offered, but responsiveness is key in a remote team.

📝 Enhancement Note: The "TELECOMMUTE" and "Fully Remote" designation is key here. While the company has a physical HQ, the role is designed for remote work within the US. This necessitates strong self-discipline, communication, and asynchronous collaboration skills from the candidate.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio by the recruiting team. This is a critical step where your portfolio must clearly demonstrate the required skills and experience.

• Hiring Manager Interview: A conversation with Kruise Sapstein (Head of Design) to discuss your design philosophy, experience, portfolio highlights, and cultural fit. Expect questions about your approach to problem-solving, collaboration, and handling complex design challenges.

• Team/Cross-Functional Interviews: Interviews with Product Managers, Engineers, and potentially other designers or data scientists. These interviews will assess your ability to collaborate, articulate design rationale, and understand technical constraints and product goals. Case study presentations or design exercises may be part of this stage.

• Final Interview: Potentially with Art Agrawal (CEO & Head of Product) or other senior leaders to discuss strategic alignment and overall fit.

Portfolio Review Tips:

• Curate Strategically: Select 3-5 of your strongest projects that best showcase your skills in UX thinking, data-informed design, and intuitive UI for consumer products. Prioritize projects that align with Jerry's industry (fintech, marketplaces, mobility) or demonstrate experience with complex data.

• Tell a Story: For each project, clearly define the problem, your role, the process you followed, the decisions you made, and the results achieved. Use visuals effectively to illustrate your journey.

• Highlight Data & AI: Explicitly detail how you used data, analytics, or research to inform your design. If you have experience applying AI to design, showcase this prominently, as it's a key area for Jerry.

• Showcase Figma Proficiency: Ensure your portfolio includes examples that demonstrate your skills in Figma, from wireframing to high-fidelity interactive prototypes.

• Quantify Impact: Where possible, use metrics to demonstrate the success of your designs (e.g., increased conversion rates, improved user satisfaction, reduced task completion times).

Challenge Preparation:

• Be prepared for a potential design exercise or case study. This might involve analyzing a problem statement and proposing a design solution, or critiquing an existing interface.

• Practice articulating your design process and rationale clearly and concisely. Be ready to defend your design decisions and explain trade-offs.

• Research Jerry.ai’s existing products to understand their current design language, user experience, and market position.

📝 Enhancement Note: The interview process will heavily rely on the candidate's portfolio. Applicants should prepare to deeply discuss their past projects, focusing on the "how" and "why" behind their design decisions, especially concerning data utilization and user problem-solving.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Essential for wireframing, UI design, prototyping, and collaboration. Candidates must be highly proficient.

• Prototyping Tools: Experience with rapid prototyping tools integrated with Figma or standalone tools for creating interactive user experiences.

Analytics & Reporting:

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

• Familiarity with A/B testing methodologies and tools to validate design hypotheses.

CRM & Automation: While not directly a designer's tool, understanding the user journeys that lead into or out of CRM and automation systems (e.g., Salesforce, HubSpot, marketing automation platforms) can be beneficial for designing holistic user experiences.

Other Potential Tools:

• User research platforms (e.g., UserTesting.com, Maze)

• Design system tools and methodologies.

• Collaboration tools (e.g., Slack, Jira, Confluence).

📝 Enhancement Note: Figma is explicitly called out as a required skill. Proficiency in analytics and experimentation tools is also crucial, emphasizing the data-informed nature of the role. While not directly using CRM or automation tools, an understanding of their role in the user journey would be a plus.

👥 Team Culture & Values

Operations Values:

• High Craft & Quality: A commitment to delivering polished, intuitive, and visually appealing designs that elevate the user experience.

• Data-Driven Decision Making: Prioritizing user research, analytics, and experimentation to inform and validate design choices.

• User-Centricity: Deep empathy for users and a relentless focus on simplifying complex problems into effortless experiences, especially in the context of car ownership.

• Collaboration & Ego-lessness: Working effectively and respectfully with cross-functional teams, valuing collective input and focusing on the best outcome for the product.

• Innovation & AI Application: Embracing new technologies, particularly AI, to find novel solutions and improve user clarity, personalization, and automation.

Collaboration Style:

• Cross-functional Integration: Design is deeply integrated with Product Management, Engineering, and Data Science, requiring close partnership and open communication.

• Iterative & Agile: A fast-paced environment that embraces iteration based on feedback, data, and experimentation.

• Transparent Communication: Open sharing of ideas, feedback, and design rationale through tools like Slack, Figma comments, and regular meetings.

• Focus on Impact: The team is driven by tangible results and measurable outcomes, aligning design efforts with business objectives.

📝 Enhancement Note: The culture emphasizes a blend of high-quality design execution with a rigorous, data-informed approach. The "ego-less" aspect suggests a collaborative environment where constructive feedback is welcomed and the focus is on achieving the best product outcomes.

⚡ Challenges & Growth Opportunities

Challenges:

• Simplifying Complexity: Effectively translating the multifaceted and often data-heavy aspects of car ownership (insurance, maintenance, repairs, financing) into simple, intuitive user experiences.

• Balancing Innovation and Usability: Incorporating AI and new technologies while ensuring the core user experience remains accessible and easy to understand for a broad audience.

• Remote Collaboration: Maintaining seamless collaboration, communication, and design quality within a fully remote, distributed team.

• Driving Measurable Impact: Proving the direct impact of design contributions on key business metrics in a data-rich environment.

Learning & Development Opportunities:

• Specialization in AI-Driven Design: Gaining expertise in how AI can be leveraged to enhance consumer product experiences.

• Impactful Product Design: Contributing to a product that aims to disrupt a massive market, offering significant opportunities for professional growth and recognition.

• Design System Evolution: Playing a role in shaping and scaling a design system for a rapidly growing consumer application.

• Cross-Functional Expertise: Deepening understanding of product management, engineering, and data science through close collaboration.

📝 Enhancement Note: The primary challenge lies in simplifying a complex domain using design and AI. The growth opportunities are tied to the company's ambitious goals and the opportunity to work on a product with significant market potential.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to design for a highly complex or data-intensive product. How did you approach simplifying it?" (Focus on your process, user research, and iterative design).

• "How do you incorporate data and analytics into your design process? Can you provide an example?" (Highlight your comfort with data, experimentation, and measuring design impact).

• "Walk me through a project where you collaborated closely with Product Managers and Engineers. How did you handle disagreements or trade-offs?" (Emphasize communication, negotiation, and achieving shared goals).

• "How would you approach designing a feature that leverages AI to personalize the car ownership experience for users?" (Discuss potential AI applications, user benefits, and ethical considerations). Company & Culture Questions:

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

• "How do you contribute to a 'high-craft' design culture, especially in a remote setting?" (Discuss your standards, attention to detail, and how you foster quality).

• "Describe your experience working within or evolving design systems." (Be ready to discuss consistency, scalability, and collaboration). Portfolio Presentation Strategy:

• Structure: Organize your presentation logically, starting with an overview of Jerry.ai and the role, then diving into 1-2 key portfolio projects.

• Narrative: Tell a compelling story for each project, highlighting the problem, your solution, your process, and the impact.

• Visuals: Use high-quality visuals of your designs, prototypes, and user flows.

• Data Focus: Clearly explain how data influenced your decisions and the outcomes achieved.

• AI Integration: If applicable, explain how AI was used or could be used to enhance the user experience in your projects.

• Q&A: Be prepared for in-depth questions about your design choices, technical skills, and collaborative approach.

📝 Enhancement Note: Interview preparation should focus on demonstrating a strong understanding of the design process, data-informed decision-making, and collaborative problem-solving, all within the context of simplifying complex user experiences.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the provided Ashby link (https://jobs.ashbyhq.com/Jerry.ai/e6f3914e-ecd8-46f8-9157-271f315caf5f).

• Portfolio Customization: Tailor your portfolio to highlight projects that best demonstrate your experience with complex data, consumer-facing products, and intuitive UI design. Emphasize your process and data-informed decision-making.

• Resume Optimization: Ensure your resume clearly outlines your 5+ years of experience, proficiency in Figma, and any relevant industry experience (fintech, insurance, mobility). Use keywords from the job description, such as "UX Thinking," "Data-Informed Design," and "Consumer-Facing Products."

• Interview Preparation: Practice articulating your design process, rationale, and impact for key portfolio projects. Prepare specific examples to answer behavioral and situational interview questions.

• Company Research: Thoroughly research Jerry.ai’s mission, products, and current market positioning. Understand their use of AI and their goal to simplify car ownership.

⚠️ 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.