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: 2026-04-07

Experience Level: 5+ Years

Remote Status: Fully Remote (within the United States)

🚀 Role Summary

• Spearhead end-to-end product design initiatives for a rapidly scaling AI-powered car ownership platform, impacting millions of users.

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

• Collaborate closely with cross-functional teams, including Product Management, Engineering, and Data Science, to drive measurable product outcomes.

• Contribute to the evolution of Jerry's design system, ensuring consistency and elevating the overall craft and quality of user interfaces.

• Leverage user research, analytics, and experimentation to inform design decisions and validate innovative solutions.

📝 Enhancement Note: While the title is "Sr. Product Designer," the responsibilities and required experience (5+ years) suggest a role that requires significant autonomy and strategic input, aligning with senior-level expectations. The emphasis on translating complex data into simple workflows and leading UX explorations indicates a strong focus on problem-solving and strategic design thinking, critical for a Senior Product Designer role in a data-intensive environment like Jerry.ai.

📈 Primary Responsibilities

• Partner with Product Managers and Engineers to thoroughly define user problems, identify core needs, and scope design solutions that align with business objectives and drive key performance indicators.

• Develop comprehensive user flows, low-fidelity wireframes, interactive prototypes, and high-fidelity UI designs for new features and enhancements across Jerry's core mobile and web applications.

• Lead UX explorations for intricate challenges, strategically structuring workflows to simplify the complexities of car ownership and management for a diverse user base.

• Utilize user research findings, product analytics, and A/B testing results to iteratively inform and validate design decisions, ensuring a data-driven approach to product development.

• Collaborate with a team of designers to maintain and evolve the company's design system, promoting consistency, scalability, and a high standard of visual and interaction design.

• Thoughtfully integrate AI capabilities into the user experience to enhance clarity, deliver personalized interactions, and automate routine tasks, making car ownership more effortless.

• Present design concepts, rationale, and outcomes effectively to stakeholders across Product, Engineering, and Leadership, fostering alignment and gathering constructive feedback.

📝 Enhancement Note: The responsibilities highlight a blend of strategic UX leadership and detailed UI execution. The emphasis on "structuring workflows," "simplifying data-heavy experiences," and "applying AI" indicates a need for a designer who can not only create beautiful interfaces but also architect robust and intelligent user journeys.

🎓 Skills & Qualifications

Education:

Experience:

• Minimum of 5 years of professional experience in designing consumer-facing mobile or web products, with a preference for experience gained within agency or in-house product teams.

Required Skills:

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

• Figma Proficiency: Advanced skills in Figma for UI design, prototyping, and collaboration.

• Prototyping Expertise: Proven ability to create rapid, functional prototypes to effectively communicate design concepts and user flows.

• Complex Problem Solving: Demonstrated ability to break down intricate user problems and design simplified, scalable solutions.

• Data-Informed Design: Experience leveraging user research, analytics, and experimentation to guide design decisions and measure impact.

• Design Systems: Understanding of design system principles, with experience in either using, contributing to, or evolving existing systems for consistency and scale.

• Cross-Functional Collaboration: Excellent communication and interpersonal skills, with a proven ability to collaborate effectively with Product Managers, Engineers, and Data Scientists.

• UI/UX Design: Comprehensive knowledge of user-centered design principles, interaction design, and visual design best practices for both mobile and web platforms.

Preferred Skills:

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

• Familiarity with AI/ML applications in product design.

• Experience with user research methodologies and usability testing.

• Knowledge of front-end development principles (HTML, CSS, JavaScript) to better inform design feasibility.

📝 Enhancement Note: The requirements clearly prioritize a strong portfolio and practical experience over formal education. The emphasis on "data-informed decision making" and "leveraging research, analytics, and experimentation" points to a need for a designer who is analytical and results-oriented, not just aesthetically focused. The bonus skills highlight a desire for candidates who can quickly ramp up in Jerry's specific domain.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• End-to-End Case Studies: Showcase at least 2-3 detailed case studies that illustrate your process from problem identification through to final design solution and its impact.

• Problem Definition: Clearly articulate the user problem or business challenge you addressed, including any initial research or discovery phases.

• Design Process Visualization: Demonstrate your design process, including user flows, wireframes, information architecture, and iteration on concepts.

• Data & User Insights: Provide evidence of how data, user research, or analytics informed your design decisions and led to specific outcomes.

• UI/Visual Design: Include high-fidelity mockups and interactive prototypes that highlight your aesthetic sensibility and attention to detail.

• Impact & Results: Quantify the impact of your design solutions with relevant metrics (e.g., conversion rates, engagement, task completion, user satisfaction).

Process Documentation:

• Candidates should be prepared to discuss their approach to user research, usability testing, design system management, and collaboration with engineering and product teams.

• Be ready to articulate how you would structure and simplify complex workflows, particularly those involving data or AI.

📝 Enhancement Note: For a Senior Product Designer role, the portfolio is critical. It's not just about showcasing pretty screens, but demonstrating a strategic, problem-solving process that yields measurable results. The emphasis on "data-informed decision making" and "quantifying impact" is key.

💵 Compensation & Benefits

Salary Range:

Benefits:

• Comprehensive health, dental, and vision coverage.

• Generous paid time off (PTO).

• Paid parental leave.

• 401(k) plan with employer matching.

• Wellness benefits.

Working Hours:

• Standard full-time hours, typically around 40 hours per week. While remote, maintaining consistent availability during core business hours for collaboration is expected.

📝 Enhancement Note: The salary range is competitive for a Senior Product Designer role in a tech company, especially in a high-cost-of-living area like Palo Alto, even for a remote position. The inclusion of equity grants is a significant perk, aligning with Jerry.ai's ambition to become a $10B company. The mention of "market-dependent" ranges suggests potential flexibility based on candidate qualifications and location.

🎯 Team & Company Context

🏢 Company Culture

Industry: Insurtech, Fintech, Automotive Technology, AI. Jerry.ai operates at the intersection of these rapidly evolving sectors, aiming to disrupt the traditional car ownership market.

Company Size: Growing rapidly, with a significant engineering and product team. The description implies a dynamic startup environment that has achieved profitability and significant funding, suggesting a blend of startup agility with established operational maturity.

Founded: 2017. This indicates a company with a few years of product development and market traction, past the initial startup phase and into a growth and scaling phase.

Team Structure:

• Design Team: Led by Kruise Sapstein (Head of Design), focusing on building a "high-performing, high-craft design culture." The team is likely small enough to allow for direct collaboration with leadership but large enough to foster diverse perspectives.

• Product Organization: A robust product organization comprising 11 Product Managers, 55 Engineers, and 12 Analysts/Data Scientists, indicating strong cross-functional collaboration and data-driven development processes.

• Leadership Involvement: Direct collaboration opportunities with the CEO & Head of Product (Art Agrawal), emphasizing a culture where design has high visibility and impact.

Methodology:

• AI-Powered Innovation: A core focus on leveraging Artificial Intelligence and Machine Learning to enhance user experience and automate processes.

• Data-Driven Development: Heavy reliance on research, analytics, and experimentation to inform product decisions and design iterations.

• Consumer-Centric Design: A commitment to simplifying complex processes and creating effortless experiences for car owners.

• Agile Development: Implied through close collaboration between design, PM, and engineering, enabling rapid iteration and quick response to market needs.

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

📝 Enhancement Note: Jerry.ai positions itself as a tech-forward company with a strong focus on AI and data. The culture appears to be collaborative, fast-paced, and ambitious, with significant opportunities for impact. The direct access to leadership and the scale of the product organization suggest a high level of accountability and visibility for senior roles.

📈 Career & Growth Analysis

Operations Career Level:

• Senior Product Designer: This role signifies an individual contributor expected to operate with a high degree of autonomy. They are responsible for complex design challenges, influencing product strategy through design, and mentoring junior designers (though not explicitly stated, this is common at the senior level). The focus is on delivering high-quality design solutions and driving measurable product outcomes.

Reporting Structure:

• Reports directly to Kruise Sapstein, Head of Design.

• Works closely with Product Managers, Engineers, and Data Scientists within specific product pods or feature teams.

Operations Impact:

• Design is positioned as a critical driver of user adoption, retention, and satisfaction for Jerry's core products, directly impacting the company's revenue and growth trajectory.

• By simplifying car ownership, the design team enables Jerry to acquire and retain the 5 million+ customers it currently serves and contributes to the goal of becoming a $10B company.

Growth Opportunities:

• Design Leadership: Potential to grow into a Lead Product Designer or Design Manager role as the design team expands.

• Specialization: Deepen expertise in specific areas like AI-driven design, complex data visualization, or platform-wide design systems.

• Cross-Functional Advancement: Develop a strong understanding of product management, data science, or engineering, potentially leading to hybrid roles or strategic product roles.

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

• Impactful Contribution: Directly shape the user experience of a product used by millions and contribute to the success of a rapidly growing, well-funded company.

📝 Enhancement Note: The "Senior" title implies a clear path for growth, either into leadership or deeper specialization within product design. The company's ambitious growth targets and focus on product excellence suggest that high performers will be recognized and rewarded with opportunities for advancement and increased responsibility.

🌐 Work Environment

Office Type:

Office Location(s):

Workspace Context:

• Digital Collaboration: Expect a work environment heavily reliant on digital tools for communication (e.g., Slack), project management (e.g., Ashby), and design collaboration (e.g., Figma).

• Asynchronous Focus: Given the remote nature, the environment likely supports asynchronous workflows, requiring clear documentation and communication practices.

• Cross-functional Interaction: Opportunities to collaborate closely with Product Managers, Engineers, and Data Scientists, fostering a highly integrated product development process.

• Design System Integration: A workspace that values and utilizes a shared design system for efficiency and consistency.

Work Schedule:

• Standard full-time hours (approx. 40 hours/week).

• Flexibility is inherent in a remote setup, but candidates should be prepared to align with core collaboration hours and team meetings to ensure effective teamwork.

📝 Enhancement Note: The fully remote nature of the role is a key aspect of the work environment. This implies a need for strong self-discipline, excellent written communication skills, and comfort with digital collaboration tools. The company's geographic distribution of talent suggests a mature approach to remote work.

📄 Application & Portfolio Review Process

Interview Process:

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

• Hiring Manager Interview: Likely a conversation with Kruise Sapstein (Head of Design) to discuss your experience, design philosophy, and approach to problem-solving. This will heavily focus on portfolio review.

• Design Challenge/Exercise: You may be given a take-home design exercise or a live design critique/problem-solving session to assess your skills in real-time.

• Cross-Functional Interviews: Meetings with Product Managers, Engineers, and/or Data Scientists to evaluate collaboration skills and technical understanding.

• Final Interview: Potentially a conversation with leadership (e.g., CEO) to discuss strategic alignment and cultural fit.

Portfolio Review Tips:

• Curate Selectively: Choose 2-4 of your strongest, most relevant case studies that demonstrate end-to-end product design thinking, particularly for complex or data-heavy applications.

• Tell a Story: For each case study, clearly articulate the problem, your process, your role, the solutions you proposed, and the measurable impact achieved. Use visuals to support your narrative.

• Highlight Data & AI: Given Jerry's focus, emphasize any projects where you've used data, analytics, or AI to inform design or improve user experiences.

• Showcase Process: Detail your iterative process, including wireframing, prototyping, user testing, and how you incorporated feedback.

• Visual Polish: Ensure your portfolio is well-designed, easy to navigate, and visually appealing, reflecting your UI/UX skills.

• Prepare to Discuss: Be ready to walk through your portfolio and answer in-depth questions about your design decisions, challenges, and outcomes.

Challenge Preparation:

• Understand the Domain: Familiarize yourself with Jerry's mission, products, and the broader Insurtech/Fintech landscape.

• Practice Problem-Solving: Be ready to tackle a design problem related to car ownership, insurance, maintenance, or data simplification. Think about user flows, potential features, and trade-offs.

• Articulate Your Rationale: For any design exercise, clearly explain why you made certain decisions, referencing user needs, business goals, and design principles.

• Demonstrate Collaboration: If it's an interview with multiple people, show how you would collaborate and incorporate feedback.

📝 Enhancement Note: The interview process is designed to thoroughly assess both design craft and strategic thinking. The portfolio is the cornerstone of the evaluation, and candidates must be prepared to deconstruct their work and demonstrate a data-driven, user-centric approach.

🛠 Tools & Technology Stack

Primary Tools:

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

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

• Design System Tools: Familiarity with tools or methodologies for managing and contributing to design systems (e.g., Storybook, Zeroheight, or Figma's component libraries).

Analytics & Reporting:

• Product Analytics Platforms: Experience with tools like Mixpanel, Amplitude, Google Analytics, or similar for tracking user behavior and product performance.

• Data Visualization Tools: Familiarity with tools that help make sense of data (e.g., Tableau, Looker, or internal dashboards) to inform design.

CRM & Automation:

• While not directly a designer's tool, understanding how CRM systems (e.g., Salesforce) and automation platforms might integrate with the user experience can be beneficial. The company likely uses internal tools for managing customer interactions and workflows.

• Project Management: Proficiency with tools like Jira, Asana, or Ashby (used by the company for hiring) to manage tasks and collaborate on projects.

📝 Enhancement Note: The emphasis on Figma and prototyping tools is standard for product designers. The mention of "analytics" and "experimentation" in the responsibilities suggests that familiarity with data analysis tools and a data-driven mindset are highly valued, even if the designer isn't directly performing the analysis.

👥 Team Culture & Values

Operations Values:

• Customer Obsession: A primary focus on simplifying car ownership and creating an effortless experience for users, driven by the company's mission.

• Data-Driven Decisions: A strong reliance on data, research, and experimentation to guide product development and design choices.

• High Craftsmanship: A commitment to producing high-quality, intuitive, and visually polished products, as evidenced by the focus on design systems and design quality.

• Collaboration & Ego-lessness: Encouraging teamwork across disciplines (design, PM, engineering, data science) and fostering an environment where ideas are shared openly and constructively.

• Ambition & Impact: A drive to disrupt a massive market and achieve significant growth, with a focus on building a $10B company.

Collaboration Style:

• Integrated Product Teams: Designers work closely within cross-functional teams, embedding into the product development lifecycle from ideation to launch and iteration.

• Transparent Communication: Emphasis on clear, open communication, likely leveraging tools like Slack and regular syncs to keep everyone aligned.

• Iterative Feedback Loops: A culture that encourages continuous feedback and iteration on designs and product features.

• Shared Ownership: While roles are defined, there's a sense of shared ownership over the product's success, fostering a collaborative spirit.

📝 Enhancement Note: The description emphasizes a culture that values both the craft of design and its impact on business outcomes. The "ego-less" and collaborative nature is crucial for a remote, cross-functional team aiming for rapid growth.

⚡ Challenges & Growth Opportunities

Challenges:

• Simplifying Complexity: Translating the intricate and often confusing world of car ownership (insurance, maintenance, financing, repairs) into a simple, intuitive user experience is a significant ongoing challenge.

• Data Interpretation: Effectively leveraging vast amounts of user data and AI insights to inform design decisions without overwhelming users or creating a sterile experience.

• Scaling Design Systems: Evolving and maintaining a design system that supports rapid feature development and a growing product suite across mobile and web.

• Cross-Functional Alignment: Ensuring seamless collaboration and communication across distributed remote teams (design, PM, engineering, data science) to maintain product velocity.

• Brand Consistency: Maintaining a strong, consistent brand identity and user experience as the product offering expands.

Learning & Development Opportunities:

• AI in Design: Deepen expertise in applying AI and ML to enhance user interfaces and user journeys.

• Complex Systems Design: Gain extensive experience in designing for complex, data-rich domains like insurance and automotive services.

• Design System Leadership: Contribute significantly to or lead the evolution of a scalable design system.

• Cross-Functional Acumen: Develop a strong understanding of product strategy, data analysis, and engineering constraints.

• Mentorship: Opportunity to mentor and guide junior designers, contributing to the growth of the design team.

• Industry Exposure: Work within a fast-growing Insurtech/Fintech company with significant funding and ambitious growth targets.

📝 Enhancement Note: The challenges are directly tied to the company's mission and the nature of its product. Overcoming these challenges presents significant opportunities for professional growth and skill development, particularly in areas like AI-driven design and complex system architecture.

💡 Interview Preparation

Strategy Questions:

• Prepare to discuss how you would approach designing a feature that simplifies car insurance comparison for users, emphasizing data points and user decision-making.

• How would you leverage AI to personalize the car maintenance experience for users, and what design considerations would be paramount?

• Describe a time you had to translate complex data into a simple, intuitive user interface. What was your process, and what was the outcome?

Company & Culture Questions:

• Research Jerry.ai's mission, values, and recent news. Understand their competitive landscape and unique value proposition.

• Be ready to discuss how your design philosophy aligns with Jerry's focus on simplicity, data, and AI.

• How do you approach collaboration with Product Managers, Engineers, and Data Scientists in a remote setting?

Portfolio Presentation Strategy:

• Start with the "Why": Clearly articulate the problem each case study solves.

• Walk Through Your Process: Explain your steps, from research and ideation to iteration and final solution. Use visuals extensively.

• Highlight Your Role: Be specific about your contributions, especially if it was a team project.

• Quantify Impact: Present metrics and outcomes to demonstrate the real-world value of your design work.

• Discuss Trade-offs: Be prepared to talk about challenges, compromises, and alternative solutions you considered.

• Showcase Figma Skills: Be ready to navigate your Figma files or demonstrate specific techniques if asked.

📝 Enhancement Note: Interview preparation should focus on demonstrating a strategic, data-informed approach to design, strong problem-solving skills, and a collaborative spirit, all tailored to Jerry.ai's specific domain and remote work environment.

📌 Application Steps

To apply for this Sr. Product Designer position:

• Submit your application through the provided link on Ashby.

• Portfolio Tailoring: Ensure your portfolio highlights end-to-end design case studies that showcase your problem-solving process, data-informed decisions, and UI/UX craft, with a focus on consumer-facing products.

• Resume Optimization: Update your resume to clearly articulate your 5+ years of experience, specific skills (Figma, prototyping, design systems), and quantifiable achievements relevant to product design.

• Interview Preparation: Practice articulating your design rationale, prepare to discuss your portfolio in detail, and research Jerry.ai's products, mission, and recent developments.

• Company Research: Understand Jerry.ai's position in the market, their AI-driven approach, and their commitment to simplifying car ownership. Be prepared to discuss how your skills can contribute to their ambitious growth goals.

⚠️ 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.