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 / GTM Operations
Date Posted: December 15, 2025
Experience Level: 5+ Years
Remote Status: Remote OK

🚀 Role Summary

• Drive the end-to-end design process for Jerry's core products, focusing on translating complex car ownership data into intuitive and engaging user experiences.
• Collaborate closely with Product Managers, Engineers, and Data Scientists to simplify data-heavy interfaces and design solutions that yield measurable business outcomes.
• Craft user flows, wireframes, prototypes, and high-fidelity UI for features across both mobile and web platforms, directly impacting customer engagement with insurance, safety, and repair services.
• Leverage user research, analytics, and experimentation to inform design decisions, validate hypotheses, and continuously improve the user experience.

📝 Enhancement Note: While the title is "Sr. Product Designer," the description emphasizes translating "complex problems and data" and leveraging "analytics and experimentation," highlighting a strong need for data-informed design and an understanding of how design impacts business metrics. This suggests a role with significant GTM and operational considerations, requiring a designer who can bridge user needs with business objectives, making it relevant to GTM Operations professionals who value data-driven product evolution.

📈 Primary Responsibilities

• Partner with Product Management and Engineering teams to define user problems, simplify complex data representations, and design intuitive workflows that enhance customer decision-making for insurance, maintenance, and repairs.
• Develop comprehensive design artifacts, including user flows, low- and high-fidelity wireframes, interactive prototypes, and final UI assets for new features and existing product enhancements across mobile and web applications.
• Lead UX explorations for intricate challenges, structuring user journeys that make the multifaceted aspects of car ownership feel simple, manageable, and even enjoyable.
• Utilize user research findings, product analytics, and A/B testing results to validate design hypotheses, measure impact, and iterate on user-centered solutions.
• Collaborate with fellow designers to maintain and evolve the company's design system, ensuring visual consistency, scalability, and a high standard of craft across all user touchpoints.
• Thoughtfully integrate AI capabilities to enhance user clarity, personalize experiences, and automate processes within the car ownership journey.

📝 Enhancement Note: The responsibilities highlight a deep involvement in translating "data-heavy experiences" and a focus on "measurable outcomes." This suggests the need for a designer who not only designs but also understands the operational impact of their designs on user acquisition, retention, and conversion, aligning with GTM operations principles.

🎓 Skills & Qualifications

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

Experience: A minimum of 5 years of professional experience in designing consumer-facing mobile or web products, whether gained in-house or at an agency.

Required Skills:

• A robust portfolio demonstrating strong UX thinking, data-informed decision-making processes, and the creation of clean, intuitive interface designs.
• Proven ability to translate complex data sets and intricate product requirements into simple, elegant, and user-friendly workflows.
• Demonstrated comfort and effectiveness in collaborating with Product Managers and Engineers to define project scope, prioritize design solutions, and iterate rapidly on product features.
• Proficiency in Figma for design and rapid prototyping, with a strong ability to clearly communicate design concepts and user interactions.
• Solid understanding of design systems, including experience in using or contributing to their development for maintaining consistency and enabling scalable design across products.
• Excellent communication and presentation skills, with the ability to articulate design rationale and technical considerations clearly to both technical and non-technical stakeholders.

Preferred Skills:

• Prior experience working within marketplaces, fintech, insurance, or mobility sectors.
• Familiarity with AI/ML applications in product design.
• Experience in evolving or establishing design systems from the ground up.
• A track record of designing for data-intensive applications.

📝 Enhancement Note: The emphasis on a portfolio showcasing "strong UX thinking, data-informed decision making" and the requirement to "translate complex data and product requirements into simple, elegant workflows" directly aligns with the analytical and process-oriented nature of operations roles. This suggests candidates with a background in operations or a strong understanding of how design impacts operational efficiency and user acquisition will be highly valued.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase a minimum of 2-3 detailed case studies illustrating end-to-end product design processes for consumer-facing applications.
• Clearly articulate the user problems addressed, the design process followed (including research, ideation, prototyping, and testing), and the rationale behind key design decisions.
• Demonstrate how data, analytics, and user feedback informed design iterations and led to measurable improvements in user experience or business metrics.
• Present high-fidelity UI designs and interactive prototypes that highlight visual polish, intuitive navigation, and a cohesive user interface.
• Include examples of work that simplify complex information or data-heavy workflows, showcasing the ability to distill intricate details into accessible user experiences.

Process Documentation:

• Within case studies, clearly document the user flow mapping and wireframing stages, emphasizing the structured approach to problem-solving and workflow design.
• Detail the prototyping and user testing phases, explaining how feedback was collected, analyzed, and integrated to refine the design and validate its effectiveness.
• Illustrate the application of design systems or UI component libraries to ensure consistency and scalability in the final design output.
• Provide evidence of collaboration with engineering teams, demonstrating an understanding of implementation constraints and how design solutions were optimized for technical feasibility.

📝 Enhancement Note: The strong emphasis on a portfolio that demonstrates "data-informed decision making" and the ability to "translate complex data and product requirements into simple, elegant workflows" is critical. Operations professionals will look for evidence of structured problem-solving, measurable impact, and how design decisions align with business objectives and user journey optimization, which are core to operations.

💵 Compensation & Benefits

Salary Range: $130,000 - $160,000 USD per year.

Benefits:

• Comprehensive health, dental, and vision insurance coverage.
• Generous paid time off (PTO) policy.
• Paid parental leave to support new parents.
• 401(K) retirement savings plan with employer matching contributions.
• Wellness benefits to support employee well-being.
• Opportunities for equity grants, providing potential for long-term financial growth.

Working Hours: Full-time, typically around 40 hours per week, with flexibility offered to accommodate remote work and individual productivity needs.

📝 Enhancement Note: The provided salary range of $130,000 - $160,000 USD for a Senior Product Designer in Palo Alto, California, is within the expected market range for this role and experience level in a high-cost-of-living area. This range reflects the seniority and specialized skills required. The inclusion of equity opportunities is a common and attractive component for senior roles in growth-stage tech companies like Jerry.ai, signaling a commitment to employee investment and long-term value creation.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology (specifically focusing on AI-powered automotive services, insurance, and car ownership management). Jerry.ai operates within the insurtech and automotive technology sectors, aiming to disrupt a $2T industry.

Company Size: The company has grown significantly, with a product organization comprising 11 Product Managers, 55 Engineers, and 12 Analysts/Data Scientists, indicating a substantial and growing tech team. The overall company size is not explicitly stated but implied to be scaling rapidly, having reached profitability and substantial funding.

Founded: Jerry.ai was founded in 2017, with its app launching in 2019. This indicates a company with a solid track record, having navigated early-stage growth and achieved significant milestones like profitability and substantial funding rounds.

Team Structure: The design team is led by Kruise Sapstein, Head of Design, and the role reports into this structure. The designer will collaborate closely with a broad product organization, including Product Managers, Engineers, and Data Scientists, suggesting a highly cross-functional and collaborative environment. The CEO, Art Agrawal, is also actively involved in shaping customer experience.

Methodology: The company emphasizes an AI-powered approach to simplify car ownership. Design decisions are informed by research, analytics, and experimentation. There's a stated focus on "high-craft design culture" and translating "complex problems and data into clear, intuitive, and visually polished experiences."

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

📝 Enhancement Note: Jerry.ai's focus on disrupting a $2T industry with an AI-powered "super app" for car ownership positions it as an ambitious player. The "high-craft design culture" and emphasis on data-informed decision-making are key indicators for operations professionals, suggesting a data-driven and user-centric approach to product development and GTM strategies. The active involvement of the CEO in customer experience further underscores the importance of product and design.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a Senior Product Designer, indicating a mid-to-senior level of experience and responsibility. It requires a candidate who can operate with a significant degree of autonomy, lead design initiatives, and mentor junior designers (implied by the "raise our craft bar" responsibility).

Reporting Structure: The Senior Product Designer will report to Kruise Sapstein, Head of Design. This structure suggests direct access to design leadership and an opportunity to influence the design vision and team culture. Collaboration will be extensive with Product Managers, Engineers, and Data Scientists, highlighting a cross-functional reporting dynamic.

Operations Impact: The role has a direct impact on the user experience of millions of people, influencing how they manage critical aspects of car ownership like insurance, financing, safety, and repairs. By simplifying complex processes and making data accessible, the designer will contribute to user acquisition, retention, and overall customer satisfaction, which are key operational metrics for growth and profitability. The ability to "design solutions that drive measurable outcomes" directly links design to business performance.

Growth Opportunities:

• Design Leadership: Potential to grow into a Lead Product Designer role, taking on more strategic ownership and potentially managing a small team or a specific product area.
• Skill Specialization: Opportunity to deepen expertise in AI-driven design, data visualization, or user research methodologies within the automotive and fintech sectors.
• Cross-Functional Advancement: With strong performance and a deep understanding of product and business metrics, there could be pathways into Product Management or Product Operations roles, leveraging design expertise in a broader GTM context.
• Mentorship: Opportunity to mentor junior designers and contribute to building a robust design culture.

📝 Enhancement Note: The "Senior" title and emphasis on driving "measurable outcomes" and "simplifying data-heavy experiences" suggest this role is crucial for operational efficiency and GTM success. A candidate who can demonstrate how their design work directly contributes to conversion rates, user adoption, or cost reduction will be highly attractive. The growth opportunities hint at potential career paths that blend design with operational strategy.

🌐 Work Environment

Office Type: The job is listed as "TELECOMMUTE," indicating a primary remote work arrangement. The company is headquartered in Palo Alto, California, suggesting a strong presence in the tech hub, but the role is accessible to candidates across the United States.

Office Location(s): Palo Alto, California, United States (Company Headquarters). However, the role is described as "Remote OK" and allows telecommuting.

Workspace Context:

• Remote Collaboration: Expect a highly collaborative environment conducted primarily through digital tools (e.g., Slack, Zoom, Figma, project management software).
• Tooling: Access to industry-standard design and collaboration tools, including Figma for design and prototyping, and likely other platforms for communication, project management, and data analysis.
• Team Interaction: While remote, the emphasis on collaboration with PMs, engineers, and data scientists suggests regular virtual meetings, design critiques, and brainstorming sessions.

Work Schedule: Full-time, with an expectation of around 40 hours per week. The remote nature offers flexibility in structuring the workday, allowing individuals to optimize their productivity around core collaboration times, which is beneficial for deep work and iterative design processes.

📝 Enhancement Note: The "Remote OK" status for a Senior Product Designer in Palo Alto is a significant draw. For operations professionals, this implies a company that is mature enough to manage a distributed workforce effectively, likely with established processes for remote collaboration and communication, which is a key operational consideration.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio to assess experience, skills, and alignment with the role's requirements.
• Portfolio Presentation & Discussion: A deeper dive into your portfolio, where you will present 1-2 case studies. This will focus on your design process, problem-solving approach, decision-making rationale, and the impact of your work. Be prepared to discuss how you used data and user research.
• Cross-Functional Interviews: Interviews with Product Managers, Engineers, and possibly Data Scientists to assess your collaboration style, communication skills, and ability to translate complex requirements into elegant solutions.
• Hiring Manager Interview: A discussion with Kruise Sapstein (Head of Design) to evaluate your fit with the design team's culture, your leadership potential, and your vision for design at Jerry.ai.
• Final Round/Offer: Potential for a final discussion with leadership and offer negotiation.

Portfolio Review Tips:

• Storytelling: Structure your case studies as compelling narratives. Clearly define the problem, your role and process, the challenges encountered, your solutions, and the measurable outcomes.
• Data & Metrics Focus: Highlight how you used data (analytics, user research, A/B tests) to inform your design decisions and quantify the impact of your work. Use specific metrics where possible.
• Process Clarity: Clearly outline your design process, from initial ideation and user flows to wireframing, prototyping, and final UI. Show your thinking at each stage.
• Visual Polish: Ensure your portfolio is visually appealing, well-organized, and easy to navigate. High-quality mockups and prototypes are essential.
• Company Alignment: Tailor your presentation to Jerry.ai's mission and focus on car ownership and AI. Showcase examples that demonstrate your ability to simplify complex, data-intensive experiences.

Challenge Preparation:

• Be prepared for a potential design exercise or take-home challenge that assesses your problem-solving skills, UX thinking, and ability to design for complex, data-driven scenarios.
• Practice articulating your design decisions concisely, focusing on the "why" behind your choices, especially concerning user needs and business objectives.
• Think about how you would approach designing features related to insurance, maintenance, or car financing, considering the data-heavy nature of these domains.

📝 Enhancement Note: The emphasis on portfolio review and case studies is crucial for operations professionals. They will be looking for evidence of structured problem-solving, data-driven decision-making, and the ability to translate complex requirements into actionable designs that yield measurable results. Preparing to discuss the "how" and "why" behind design choices, with a focus on impact, is key.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Essential for UI design, wireframing, prototyping, and collaboration.
• Prototyping Tools: Proficiency in Figma's prototyping capabilities or other rapid prototyping tools (e.g., InVision, ProtoPie) is expected.
• Design System Tools: Experience with tools or methodologies for managing and contributing to design systems.

Analytics & Reporting:

• Analytics Platforms: Familiarity with tools like Google Analytics, Amplitude, Mixpanel, or similar platforms to understand user behavior and inform design decisions.
• Data Visualization Tools: Experience interpreting data presented in dashboards or reports from tools like Tableau, Looker, or internal BI systems can be beneficial.

CRM & Automation:

• While not directly a CRM/Automation role, understanding how design impacts user journeys within CRM and marketing automation workflows could be an advantage. Familiarity with how user data is managed and leveraged is helpful.

📝 Enhancement Note: The explicit mention of Figma and rapid prototyping tools is standard for product design. However, the implicit need to leverage "research, analytics, and experimentation" suggests that familiarity with or the ability to quickly learn common analytics platforms (like Amplitude or Mixpanel) and understand how design integrates with data reporting is highly valued, aligning with the data-centric nature of operations.

👥 Team Culture & Values

Operations Values:

• Data-Driven Decision Making: A core value, evident in the emphasis on using research, analytics, and experimentation to guide design choices and measure impact.
• User-Centricity: Designing for millions of users requires a deep understanding of their needs and pain points, translating complex car ownership into effortless experiences.
• High Craftsmanship: A commitment to delivering polished, intuitive, and visually appealing user interfaces.
• Collaboration & Ego-lessness: Working effectively within cross-functional teams, valuing collective problem-solving over individual accolades, and fostering a "high-craft design culture."
• Innovation & AI Application: Embracing new technologies like AI to enhance user experiences and automate processes.

Collaboration Style:

• Cross-Functional Integration: Close partnership with Product Management, Engineering, and Data Science teams, requiring clear communication and shared understanding of goals.
• Iterative Design: A culture of continuous improvement through feedback loops, A/B testing, and agile development practices.
• Knowledge Sharing: Contributing to the design system and participating in design critiques to elevate the team's overall skill and output.

📝 Enhancement Note: The company's stated values of "Data-Driven Decision Making," "High Craftsmanship," and "Collaboration" are highly relevant to operations professionals. These values suggest an environment where efficiency, measurable results, and teamwork are paramount, aligning with the core tenets of revenue and sales operations.

⚡ Challenges & Growth Opportunities

Challenges:

• Simplifying Complexity: The primary challenge is translating the inherently complex and data-intensive aspects of car ownership (insurance, financing, repairs) into simple, intuitive user experiences for a broad audience.
• Balancing User Needs and Business Goals: Ensuring that design solutions meet user needs while also driving measurable business outcomes like acquisition, retention, and profitability.
• Evolving Design System: Maintaining and scaling a design system across multiple product areas and platforms in a rapidly growing company.
• AI Integration: Effectively and ethically integrating AI into the user experience to provide genuine value without overwhelming users.

Learning & Development Opportunities:

• Deep Domain Expertise: Gaining in-depth knowledge of the automotive, insurance, and fintech industries.
• AI in Design: Exploring cutting-edge applications of AI in product design and user experience.
• Data Visualization & Interpretation: Enhancing skills in understanding and visualizing complex data to inform design.
• Leadership & Mentorship: Developing leadership skills through senior responsibilities and the opportunity to mentor junior designers.

📝 Enhancement Note: The challenges listed, particularly "Simplifying Complexity" and "Balancing User Needs and Business Goals," are core to many operations roles. Understanding how design contributes to these operational challenges and how to leverage design for efficiency and growth is a valuable perspective for operations candidates.

💡 Interview Preparation

Strategy Questions:

• Design for Complexity: "Describe a time you had to design for a highly complex or data-intensive product. How did you approach simplifying it for the user, and what was the outcome?" (Focus on your structured thinking, process, and measurable results).
• Data-Informed Design: "How do you incorporate user data and analytics into your design process? Can you provide an example where data led you to change your design direction?" (Highlight your analytical skills and iterative approach).
• Collaboration Scenarios: "How do you typically collaborate with Product Managers and Engineers? Describe a situation where you had a disagreement and how you resolved it." (Emphasize communication, empathy, and problem-solving).

Company & Culture Questions:

• Jerry's Mission: "What excites you about Jerry's mission to simplify car ownership, and how do you see design contributing to that vision?" (Showcase your understanding of the company's goals and your passion).
• Design Culture: "Based on what you've learned, how do you think your design approach aligns with Jerry's 'high-craft design culture'?" (Connect your values and working style to the company's stated culture).
• AI in Design: "What are your thoughts on applying AI in product design, and how would you approach integrating it into a product like Jerry?" (Demonstrate forward-thinking and an understanding of AI's potential).

Portfolio Presentation Strategy:

• Focus on Impact: For each case study, clearly articulate the problem, your specific role and contributions, the solution, and the measurable impact (e.g., increased conversion, reduced support tickets, improved user satisfaction scores).
• Show Your Process: Walk through your design thinking, including user research, ideation, wireframing, prototyping, and testing. Explain the rationale behind key decisions.
• Data Integration: Highlight where and how data influenced your design choices. If you have metrics, present them clearly.
• Conciseness and Clarity: Be prepared to present your work within a set timeframe, ensuring your explanations are clear, concise, and engaging for a mixed audience of designers, product managers, and engineers.

📝 Enhancement Note: The interview preparation advice focuses heavily on demonstrating data-informed decision-making, structured problem-solving, and measurable impact. These are critical competencies for operations roles, so candidates should emphasize these aspects when discussing their designs and experiences.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the provided link on Ashby.
• Portfolio Customization: Tailor your portfolio to highlight projects that showcase your ability to simplify complex, data-intensive experiences and drive measurable outcomes. Prioritize case studies demonstrating strong UX thinking and data-informed decision-making.
• Resume Optimization: Ensure your resume clearly articulates your 5+ years of experience in consumer-facing product design, highlighting specific achievements and skills relevant to UI/UX, prototyping, and cross-functional collaboration. Use keywords like "UX," "Product Design," "Figma," "Data-Informed," and "User Flows."
• Interview Preparation: Practice articulating your design process and the impact of your work using the STAR method (Situation, Task, Action, Result). Be ready to discuss your portfolio in detail and answer scenario-based questions related to design challenges and collaboration.
• Company Research: Familiarize yourself with Jerry.ai's mission, products, and recent news. Understand their focus on AI, car ownership, and their growth trajectory to demonstrate genuine interest and cultural fit during interviews.

⚠️ 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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