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: 2026-06-02

Experience Level: 5-10 years

Remote Status: Remote OK

🚀 Role Summary

• Drive end-to-end product design for Jerry's AI-powered car ownership assistant, impacting millions of users daily.

• Translate complex, data-heavy user problems into intuitive, visually polished experiences across mobile and web platforms.

• Collaborate closely with Product Managers, Engineers, and Data Scientists to define user needs and design innovative solutions.

• Leverage user research, analytics, and experimentation to inform design decisions and iterate on product features.

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

📝 Enhancement Note: While the title is "Sr. Product Designer," the responsibilities clearly indicate a focus on UX/UI design within a product development context. The role emphasizes translating complex user problems and data into intuitive experiences, which is a core tenet of UX design. The integration of AI and data-driven decision-making suggests a need for designers who can not only create aesthetically pleasing interfaces but also understand and leverage quantitative insights.

📈 Primary Responsibilities

• Partner with Product Managers and Engineering teams to deeply understand user problems, define product requirements, and design elegant solutions that drive measurable business outcomes.

• Create comprehensive user flows, low-fidelity wireframes, high-fidelity mockups, and interactive prototypes to effectively communicate design concepts and user interactions.

• Lead UX explorations for complex challenges, focusing on structuring intuitive workflows for car ownership management, insurance, safety, and repairs.

• Utilize user research findings, product analytics, and A/B testing results to validate design decisions and inform iterative improvements.

• Collaborate with other designers to maintain and evolve the company's design system, ensuring brand consistency and design efficiency across the product suite.

• Thoughtfully integrate AI capabilities into the user experience to enhance clarity, deliver personalized insights, and automate user tasks where appropriate.

📝 Enhancement Note: The responsibilities outline a full-cycle design process from problem definition to iteration, with a strong emphasis on data-informed decision-making and collaboration. The mention of "structuring workflows" and "simplifying data-heavy experiences" points to a need for strong information architecture and interaction design skills. The explicit mention of applying AI suggests that candidates with experience in AI-driven product design or an understanding of AI's potential in user interfaces will be highly valued.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a Bachelor's degree in Design, Human-Computer Interaction, Computer Science, or a related field is often preferred for senior product design roles.

Experience: 5+ years of professional experience designing consumer-facing mobile or web products, with a proven track record of shipping successful features.

Required Skills:

• A strong portfolio showcasing robust UX thinking, data-informed design decisions, and clean, intuitive interface design across consumer-facing products.

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

• Demonstrated experience in creating user flows, wireframes (low- and high-fidelity), and interactive prototypes.

• Proficiency in Figma for design and rapid prototyping.

• Solid understanding of design systems and experience in either using or evolving them for consistency and scalability.

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

Preferred Skills:

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

• Familiarity with applying AI and machine learning concepts to product design.

• Experience with user research methodologies and analytics tools to inform design.

• Understanding of front-end development principles to facilitate collaboration with engineers.

📝 Enhancement Note: The experience requirement is explicitly stated as "5+ years." The portfolio requirement is heavily emphasized, with specific mentions of "strong UX thinking, data-informed decision making, and clean, intuitive interface design." The preference for experience in specific industries like "fintech, insurance, or mobility" is a key differentiator for candidates.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A curated collection of projects demonstrating end-to-end product design ownership, from initial concept to shipped product.

• Case studies that clearly articulate the problem, your design process, the solutions you developed, and the measurable impact of your work.

• Examples showcasing strong UX thinking, particularly in simplifying complex data or workflows.

• Visual examples of clean, intuitive, and aesthetically pleasing interface design for consumer-facing applications.

• Evidence of data-informed decision-making, illustrating how user data, analytics, or experimentation guided your design choices.

Process Documentation:

• Detailed explanations within case studies of how you collaborated with cross-functional teams (PMs, Engineers, Data Scientists).

• Documentation of your approach to user research, ideation, wireframing, prototyping, and usability testing.

• Examples of how you contributed to or utilized design systems.

• Illustrations of how you applied design principles to solve complex problems and improve user workflows.

📝 Enhancement Note: The portfolio requirements are a critical component of the application process, as highlighted by the explicit mention in the "What we're looking for" section. The emphasis is on showcasing a comprehensive design process, data utilization, and tangible results, which is standard for senior product design roles.

💵 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.

• Opportunities for equity grants (stock options).

Working Hours: Standard full-time hours are expected, likely around 40 hours per week, with flexibility offered due to the remote nature of the role.

📝 Enhancement Note: The salary range is clearly provided. The benefits package is detailed, including standard health insurance offerings, PTO, parental leave, retirement savings with matching, wellness programs, and equity. The mention of "equity opportunities may also be part of your total rewards package" and "In addition to base salary, the compensation may include opportunities for equity grants" confirms the inclusion of equity. The working hours are stated as 40 hours, typical for a full-time role.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology (specifically, AI-powered consumer services for car ownership, operating within the broader automotive, insurance, and fintech sectors).

Company Size: Jerry.ai is a rapidly growing company, indicated by its funding ($240M), profitability, and stated ambition to become a $10B company by 2030. The product team alone comprises 11 PMs, 55 engineers, and 12 analysts/data scientists.

Founded: Jerry.ai was founded in 2017. This suggests a company that has moved beyond the startup phase and is now focused on scaling and market expansion.

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 candidate will report to Kruise Sapstein, Head of Design.

Methodology:

• Data-Driven Design: The role emphasizes leveraging research, analytics, and experimentation to inform design decisions.

• Agile Development: Collaboration with PMs and engineers to "define scope, prioritize solutions, and iterate quickly" suggests an agile or agile-like development process.

• User-Centricity: The core mission of simplifying car ownership and the focus on user problems highlight a strong user-centric approach.

• AI Integration: A key methodology is the thoughtful application of AI to enhance user experience, clarity, and automation.

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

📝 Enhancement Note: The company's trajectory (profitability, funding, growth targets) suggests a dynamic and ambitious environment. The emphasis on "high-craft design culture" and the collaborative structure of the product team are key cultural indicators. The integration of AI is presented not just as a technology but as a core methodology for improving user experience.

📈 Career & Growth Analysis

Operations Career Level: This is a Senior Product Designer role, indicating a mid-to-senior level position requiring significant autonomy, strategic input, and the ability to mentor or guide junior designers (though explicit mentorship is not a stated primary responsibility). The role is crucial for shaping the user experience of core products.

Reporting Structure: The Senior Product Designer will report directly to the Head of Design (Kruise Sapstein). This provides direct access to design leadership and strategic decision-making.

Operations Impact: The designer's work will directly influence how millions of users interact with Jerry's products, aiming to make car ownership "easy and even enjoyable." This translates to significant impact on customer acquisition, retention, satisfaction, and ultimately, the company's valuation and market position. Their designs will underpin the company's mission to simplify a complex, $2T industry.

Growth Opportunities:

• Design Leadership: Potential to grow into a Lead Product Designer or Design Manager role as the design team expands, taking on more strategic oversight and team leadership responsibilities.

• Specialization: Opportunity to deepen expertise in AI-driven product design, consumer marketplaces, or the automotive/insurance tech space.

• Cross-Functional Influence: Develop stronger strategic partnerships with Product and Engineering leadership, influencing product roadmaps and company-wide design standards.

• Mentorship: As a senior member, there will be opportunities to mentor junior designers and contribute to building a high-craft design culture.

📝 Enhancement Note: The role is positioned as critical to the company's success and brand identity ("define our brand, and design the next generation of products"). The growth opportunities are framed around increasing leadership and specialization within a fast-growing tech company focused on a massive market.

🌐 Work Environment

Office Type: The role is listed as "TELECOMMUTE" with a primary location of Palo Alto, California, but the company also supports remote employees across the US. This indicates a distributed or remote-first work environment.

Office Location(s): While Palo Alto is listed as the primary location, the "ai_remote_location_derived" list includes: Palo Alto, California; Austin, Texas; Chicago, Illinois; Los Angeles, California; Phoenix, Arizona; Portland, Oregon. This suggests the company has a distributed workforce and is open to hiring talent across these regions.

Workspace Context:

• Remote Collaboration: Expect a highly collaborative remote environment, relying heavily on digital tools for communication, design, and project management.

• Tools & Technology: Access to industry-standard design tools like Figma, prototyping software, and collaboration platforms will be essential.

• Cross-Functional Interaction: Frequent interaction with Product Managers, Engineers, Data Scientists, and other designers is a key aspect of the daily work.

Work Schedule: While a standard 40-hour work week is implied for full-time employment, the remote nature likely allows for some flexibility in daily scheduling, provided core collaboration hours are met.

📝 Enhancement Note: The "TELECOMMUTE" and "Remote OK" designations, along with the list of supported remote locations, clearly define a remote-first or highly flexible hybrid work environment. This is a significant factor for candidates prioritizing remote work.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Application Review: Screening of resumes and portfolios for required experience, skills, and alignment with the company's mission.

• Portfolio Presentation: Candidates will likely be asked to present their portfolio, discussing specific projects, design process, and impact. This is a critical step to assess UX thinking, communication, and problem-solving abilities.

• Design Challenge/Case Study: A potential exercise to evaluate design skills in a practical scenario, possibly involving a defined problem or a critique of an existing experience.

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

• Hiring Manager Interview: A final discussion with the Head of Design (Kruise Sapstein) to delve deeper into design philosophy, leadership potential, and overall fit.

Portfolio Review Tips:

• Showcase Impact: Clearly articulate the business and user impact of your design work, using metrics and data where possible.

• Detail Your Process: Explain your thought process, the challenges you faced, and how you arrived at your solutions. Highlight data-informed decision-making.

• Focus on Complexity: Demonstrate how you simplify complex problems and data into intuitive user experiences.

• Visual Polish: Ensure your portfolio is visually appealing, well-organized, and easy to navigate.

• Figma Proficiency: Be ready to discuss your Figma workflows and any custom components or libraries you've built.

• Tailor to Jerry: Understand Jerry's mission and target audience. Highlight projects that align with their focus on simplifying car ownership and leveraging AI.

Challenge Preparation:

• Understand the Domain: Research Jerry.ai's products, competitors, and the car ownership industry.

• Think Data-Informed: Be prepared to discuss how you would use data (analytics, user feedback) to inform design decisions.

• AI Integration: Consider how AI could be applied to enhance user experiences in the automotive/insurance space.

• Problem Framing: Practice framing problems from a user-centric perspective and outlining potential solution paths.

📝 Enhancement Note: The description strongly implies a portfolio-centric hiring process. The "What we're looking for" section explicitly calls out the portfolio as a key assessment tool. The interview process is inferred to be multi-stage, involving presentations and cross-functional collaboration assessments.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Explicitly mentioned as a required skill for design and rapid prototyping. This will be the primary tool for UI design, wireframing, and prototyping.

• Prototyping Tools: Beyond Figma, experience with other rapid prototyping tools is implied, allowing for quick iteration and user testing of design concepts.

Analytics & Reporting:

• User Research Tools: While not specified, experience with tools for conducting user interviews, surveys, and usability testing is assumed.

• Product Analytics Platforms: Familiarity with platforms like Amplitude, Mixpanel, or similar tools used for tracking user behavior and measuring feature adoption is highly beneficial for data-informed design.

CRM & Automation:

• Design System Management: Understanding of how to manage and contribute to design systems, ensuring consistency and efficiency.

• Collaboration Tools: Proficiency with tools like Slack, Jira, Asana, or similar for team communication and project tracking.

📝 Enhancement Note: Figma is the only tool explicitly named. However, given the role's responsibilities, a broader toolkit including user research platforms, analytics tools, and collaboration software is implicitly required for effective execution.

👥 Team Culture & Values

Operations Values:

• High Craftsmanship: The Head of Design is focused on building a "high-performing, high-craft design culture," indicating a strong emphasis on quality, attention to detail, and excellence in design execution.

• User-Centricity: The company's mission to simplify car ownership for millions of people underscores a deep commitment to understanding and serving user needs.

• Data-Informed: Design decisions are driven by research, analytics, and experimentation, promoting a culture of evidence-based decision-making.

• Collaboration: The role requires close partnership with PMs, engineers, and data scientists, fostering a team-oriented approach to product development.

• Innovation: The use of AI and the ambition to disrupt a massive industry point to a culture that values innovative thinking and pushing boundaries.

Collaboration Style:

• Cross-functional Partnership: The role necessitates close collaboration with Product Management (defining problems, scope), Engineering (implementation feasibility), and Data Science (insights, validation).

• Design System Focus: Working with other designers to evolve and maintain the design system promotes a collaborative approach to establishing and enforcing design standards.

• Iterative & Agile: The emphasis on iterating quickly and leveraging feedback suggests an open and adaptive collaboration style, where designs are refined based on input and testing.

📝 Enhancement Note: The culture is described as "high-craft" and user-centric, with a strong emphasis on data and collaboration. The mention of "passionate, curious and egoless people" in the company description further reinforces a collaborative and driven team environment.

⚡ Challenges & Growth Opportunities

Challenges:

• Simplifying Complexity: Translating the intricate, data-heavy processes of car ownership (insurance, financing, repairs) into simple, intuitive user experiences is a significant design challenge.

• AI Integration: Thoughtfully applying AI to enhance user experience without overwhelming users or creating unintended consequences requires careful design and ethical consideration.

• Scaling Design System: Evolving and maintaining a robust design system across a growing product suite and user base requires ongoing effort and strategic planning.

• Balancing User Needs and Business Goals: Ensuring designs meet user needs while driving measurable business outcomes for a profitable and growth-oriented company.

Learning & Development Opportunities:

• Deepen AI Design Expertise: Gain hands-on experience applying AI/ML to consumer products, learning how to design for intelligent features.

• Industry Specialization: Develop deep knowledge in the automotive, insurance, or fintech sectors, becoming an expert in user needs within these domains.

• Design System Leadership: Contribute significantly to the growth and strategic direction of the company's design system.

• Mentorship & Influence: Grow into a more influential role within the design team, potentially mentoring junior designers and shaping design strategy.

📝 Enhancement Note: The challenges are directly tied to the core nature of Jerry's product and the company's ambitious goals. The growth opportunities are framed around developing specialized skills and increasing influence within a growing organization.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you translated a complex, data-heavy problem into a simple, intuitive user experience. What was your process, and what was the outcome?" (Focus on process, data usage, and impact)

• "How would you approach designing a feature that leverages AI to personalize car insurance recommendations for users?" (Focus on AI application, user empathy, and personalization)

Company & Culture Questions:

• "What interests you most about Jerry's mission to simplify car ownership?" (Demonstrate understanding of the company's value proposition)

• "How do you contribute to a 'high-craft' design culture in a remote environment?" (Address collaboration and quality standards)

Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly articulate: Problem, Your Role, Process (Research, Ideation, Design, Testing), Solution, and Impact (Metrics).

• Highlight Data: Explicitly show how data (user research, analytics, A/B tests) informed your design choices at various stages.

• Showcase Figma Skills: Be prepared to discuss your Figma workflows, components, and prototyping techniques.

• Focus on UX Thinking: Emphasize your problem-solving approach and how you arrived at your solutions, not just the final visuals.

• Tailor to Jerry: Connect your projects and skills to Jerry's specific context—simplifying car ownership and leveraging AI.

📝 Enhancement Note: Interview preparation advice focuses on demonstrating key skills mentioned in the job description: UX thinking, data-informed design, AI application, and portfolio presentation. The questions are designed to elicit examples of these competencies.

📌 Application Steps

To apply for this Sr. Product Designer position:

• Submit your application through the provided link on Ashby.

• Curate Your Portfolio: Select 2-3 of your strongest projects that best showcase your UX thinking, data-informed decision-making, and clean interface design for consumer-facing products. Ensure each project tells a clear story of problem, process, solution, and impact.

• Optimize Your Resume: Tailor your resume to highlight your 5+ years of experience in consumer product design, proficiency in Figma and prototyping, and any relevant industry experience (fintech, insurance, mobility). Quantify achievements wherever possible.

• Prepare Your Presentation: Practice presenting your portfolio, focusing on articulating your design process, how you leveraged data, and the measurable outcomes of your work. Be ready to discuss your approach to simplifying complex problems.

• Research Jerry.ai: Thoroughly understand Jerry's mission, products, target audience, and recent company news. Consider how your design philosophy aligns with their goal of making car ownership effortless and their use of AI.

⚠️ 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.