Sr. Product Designer

📍 Job Overview

Job Title: Sr. Product Designer

Company: Jerry.ai

Location: Palo Alto, California, United States (Remote OK)

Job Type: FULL_TIME

Category: Product Design / UX/UI

Date Posted: 2026-05-04

Experience Level: 5-10 Years

🚀 Role Summary

• Drive the end-to-end design process for Jerry's core AI-powered car ownership products, ensuring intuitive and engaging user experiences.

• Translate complex data, user needs, and product requirements into clear, elegant, and visually polished interfaces for both mobile and web platforms.

• Collaborate closely with Product Managers, Engineers, and Data Scientists to define user problems and design solutions that achieve measurable business outcomes.

• Contribute to the evolution and maintenance of Jerry's design system, promoting consistency and scalability across all product touchpoints.

• Leverage user research, analytics, and experimentation to inform design decisions and continuously optimize the user journey.

📝 Enhancement Note: This role is critical for translating complex, data-heavy functionalities in the car ownership space into user-friendly experiences. The emphasis on AI integration and end-to-end ownership suggests a highly impactful position within a fast-growing, profitable company.

📈 Primary Responsibilities

• Lead the creation of user flows, wireframes, prototypes, and high-fidelity UI designs for new features and enhancements across Jerry's product suite.

• Conduct UX explorations for complex problem spaces, structuring intuitive workflows that simplify the car ownership and management experience.

• Partner with Product Managers and Engineers to define user problems, scope solutions, and iterate rapidly based on feedback and data.

• Utilize user research findings, product analytics, and A/B testing results to validate design decisions and drive continuous improvement.

• Apply thoughtful design solutions that integrate AI capabilities to enhance clarity, personalization, and automation within the user experience.

• Collaborate with other designers to maintain and evolve the design system, ensuring visual consistency and efficient design implementation.

• Advocate for user-centered design principles throughout the product development lifecycle, influencing product strategy and roadmap.

📝 Enhancement Note: The responsibilities highlight a blend of strategic UX thinking, detailed UI execution, and a data-informed approach, typical of senior design roles in consumer tech. The direct mention of "structuring workflows" and "simplifying data-heavy experiences" points to a need for strong problem-solving skills in a complex domain.

🎓 Skills & Qualifications

Education: While no specific degree is listed, a Bachelor's or Master's degree in Design, Human-Computer Interaction, or a related field is typically preferred for senior roles.

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

Required Skills:

• Demonstrated portfolio showcasing strong UX thinking, data-informed decision-making, and clean, intuitive interface design.

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

• Expertise in creating user flows, low- and high-fidelity wireframes, and interactive prototypes.

• Proficiency with design and prototyping tools, specifically Figma.

• Strong understanding of design systems, including their creation, maintenance, and application for consistency and scale.

• Excellent communication and collaboration skills, with the ability to articulate design rationale clearly to diverse stakeholders (technical and non-technical).

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

Preferred Skills:

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

• Understanding of AI/ML principles and their application in user experience design.

• Experience with evolving or contributing to existing design systems.

• Background in agency or in-house product design roles.

📝 Enhancement Note: The emphasis on a portfolio with "strong UX thinking" and "data-informed decision making" is crucial. The required skill set points to a designer who can operate independently, manage complex projects, and influence product direction, aligning with a senior-level position.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

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

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

• Examples highlighting your ability to simplify complex, data-heavy experiences and design intuitive workflows.

• Visual examples of clean, polished interface design across mobile and web platforms.

Process Documentation:

• Showcase your approach to user research, including methods used and how insights were integrated into the design process.

• Detail your workflow for translating product requirements and complex data into user flows, wireframes, and prototypes.

• Provide examples of how you've collaborated with Product Managers and Engineers, demonstrating your ability to define scope and iterate quickly.

• Illustrate your understanding and application of design systems to ensure consistency and scalability.

📝 Enhancement Note: For a Senior Product Designer role, the portfolio is paramount. It needs to go beyond just showcasing aesthetics; it must demonstrate strategic thinking, problem-solving capabilities, and a results-oriented approach, particularly in a data-intensive domain like car ownership.

💵 Compensation & Benefits

Salary Range: $150,000 - $200,000 USD per year.

Benefits:

• Comprehensive health, dental, and vision coverage.

• Generous paid time off (PTO).

• Paid parental leave.

• 401(K) plan with employer matching.

• Wellness benefits.

• Opportunities for equity grants and stock options, reflecting the company's growth trajectory and profitability.

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

📝 Enhancement Note: The salary range is competitive for a Senior Product Designer in the Palo Alto/Bay Area, even for a remote role. The inclusion of equity grants and stock options is a significant indicator of the company's growth potential and its desire to attract and retain key talent in a high-impact role. The benefits package is robust and aligns with industry standards for tech companies.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, specifically focused on the automotive/mobility and fintech/insurance sectors, leveraging AI. Jerry.ai is building a "super app" for car ownership.

Company Size: Jerry.ai has grown significantly, with over 5 million customers and a team structure that includes 11 PMs, 55 engineers, and 12 analysts/data scientists, indicating a medium-to-large size tech organization.

Founded: Founded in 2017, Jerry.ai has a proven track record and has achieved profitability, backed by substantial funding.

Team Structure:

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

• Designers will work within a larger product organization comprising Product Managers, Engineers, and Data Scientists, fostering cross-functional collaboration.

Methodology:

• Data-driven decision-making is a core principle, with heavy reliance on analytics and experimentation.

• A strong emphasis on user-centered design to simplify complex processes.

• Application of AI and machine learning to enhance product functionality and user experience.

• Iterative development cycles, encouraging rapid prototyping and feedback loops.

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

📝 Enhancement Note: Jerry.ai presents itself as an ambitious, AI-driven company disrupting a massive, traditional industry. The culture appears to value high performance, craft, and data-informed decisions, with a clear vision for growth and market leadership. The collaborative structure suggests an environment where designers can have significant influence.

📈 Career & Growth Analysis

Operations Career Level: This is a Senior Product Designer role, indicating a mid-to-senior level position with significant autonomy and responsibility. The expectation is for the designer to lead complex projects, mentor junior designers (if applicable), and significantly influence product strategy and user experience.

Reporting Structure: The role reports directly to the Head of Design, Kruise Sapstein. This close reporting line suggests opportunities for direct mentorship and high visibility. Collaboration will be extensive with Product Managers, Engineers, and Data Scientists.

Operations Impact: The Senior Product Designer will have a direct impact on how millions of users interact with Jerry's platform, influencing customer acquisition, retention, and satisfaction. Their work will be instrumental in simplifying car ownership, a critical and often frustrating aspect of daily life for many Americans, directly contributing to the company's mission and growth targets.

Growth Opportunities:

• Skill Development: Opportunity to deepen expertise in AI-driven design, complex data visualization, and designing for marketplaces/fintech. Exposure to a rapidly scaling product and design system.

• Leadership Potential: Potential to grow into a Lead Product Designer or Design Manager role as the design team expands. Opportunity to shape design processes and mentor emerging talent.

• Industry Expertise: Gain deep experience in the automotive, insurance, and fintech sectors, highly valuable in a growing market.

• Strategic Influence: Contribute to product strategy discussions and influence the direction of a rapidly scaling, profitable tech company with ambitious growth targets.

📝 Enhancement Note: This senior role offers substantial growth potential, not just in design execution but also in strategic influence and leadership within a high-growth tech company. The direct reporting to the Head of Design and the company's expansion plans provide a clear path for career advancement.

🌐 Work Environment

Office Type: While the job is listed as TELECOMMUTE and remote, the company has physical locations (Palo Alto, CA). The "Remote OK" status suggests a hybrid or fully remote approach is acceptable, with potential for occasional in-person collaboration or team events.

Office Location(s): Palo Alto, California, with potential satellite locations or remote work options in Austin, Chicago, Los Angeles, Phoenix, Portland, and the San Francisco Bay Area.

Workspace Context:

• The role is designed for remote work, offering flexibility.

• Collaboration will likely occur through digital tools (Slack, Figma, video conferencing), facilitating interaction with a distributed team.

• The environment is described as fast-paced and driven by a "passionate, curious and egoless" team focused on solving real-world problems.

• Access to a robust tech stack including Figma and rapid prototyping tools will support the design workflow.

Work Schedule: Standard full-time, likely with flexibility to accommodate remote work and project demands. While 40 hours per week is typical, the emphasis on rapid iteration and impact may require adaptability.

📝 Enhancement Note: The "Remote OK" designation with specific location preferences suggests a company that embraces flexible work arrangements while potentially valuing some level of regional alignment for collaboration or team gatherings. The focus is on delivering results regardless of physical location.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Review of application and portfolio to assess qualifications and fit.

• Portfolio Presentation & Discussion: A deep dive into the candidate's portfolio, focusing on UX thinking, problem-solving, design process, and impact. Candidates will be expected to articulate their rationale and decision-making.

• Skills-Based Exercise/Challenge: Potentially a design challenge or a collaborative problem-solving session with PMs and engineers to assess practical skills, communication, and approach to complex problems.

• Team/Culture Fit Interviews: Meetings with the Head of Design, CEO, and potentially other team members to evaluate collaboration style, cultural alignment, and communication effectiveness.

• Final Round: Possibly with senior leadership to discuss strategic alignment and long-term vision.

Portfolio Review Tips:

• Curate Strategically: Select 3-4 of your strongest projects that best showcase your skills in UX thinking, data-informed design, and UI craft, ideally with examples relevant to consumer tech, fintech, or mobility.

• Tell a Story: For each project, clearly outline the problem, your role, your process (research, ideation, iteration), the solutions you designed, and the measurable outcomes or learnings. Quantify impact wherever possible.

• Highlight Complexity: Emphasize projects where you translated complex data or requirements into simple, elegant solutions. Showcase your ability to structure intuitive workflows.

• Showcase Collaboration: Briefly mention how you collaborated with PMs, engineers, and stakeholders, and how you incorporated their feedback.

• Be Ready to Discuss: Prepare to walk through your process, defend your design decisions, and answer questions about your rationale, tools, and methodologies.

Challenge Preparation:

• Understand the Domain: Familiarize yourself with Jerry.ai's product, target audience, and the challenges of simplifying car ownership.

• Practice Problem-Solving: Be prepared to tackle hypothetical design problems related to user flows, feature design, or optimizing existing experiences.

• Articulate Your Process: Practice explaining your design thinking step-by-step, focusing on user needs, constraints, and desired outcomes.

• Communicate Clearly: Focus on clear, concise communication, especially when presenting your work or discussing solutions with a diverse group.

📝 Enhancement Note: The interview process is designed to thoroughly evaluate a candidate's design capabilities, strategic thinking, and cultural fit. The portfolio review is a critical component, requiring candidates to demonstrate not just design skill but also a deep understanding of user problems and business impact.

🛠 Tools & Technology Stack

Primary Tools:

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

• Prototyping Tools: Experience with rapid prototyping tools (often integrated within Figma or standalone like InVision, ProtoPie) is expected for communicating ideas effectively.

Analytics & Reporting:

• Familiarity with leveraging product analytics tools (e.g., Amplitude, Mixpanel, Google Analytics) to inform design decisions and measure impact.

CRM & Automation:

• While not directly a CRM role, understanding how design integrates with user journeys managed by CRM and automation platforms is beneficial.

• Experience designing for platforms that might utilize AI for personalization and automation.

📝 Enhancement Note: Proficiency in Figma is a non-negotiable requirement. The emphasis on data and experimentation implies that designers are expected to work closely with analytics tools and contribute to data-informed product development.

👥 Team Culture & Values

Operations Values:

• High Craft & Impact: A strong emphasis on producing high-quality design work that drives measurable business outcomes and user satisfaction.

• Data-Informed: Decisions are grounded in user research, analytics, and experimentation, ensuring designs are effective and aligned with business goals.

• Collaboration & Ego-Less: Working effectively in cross-functional teams, valuing diverse perspectives, and focusing on collective success over individual recognition.

• Simplification & Intuition: A core drive to make complex processes (like car ownership) feel effortless and intuitive for users.

• Innovation & AI Application: Embracing new technologies, particularly AI, to create groundbreaking solutions and improve user experiences.

Collaboration Style:

• Cross-functional Integration: Designers are expected to work closely and collaboratively with Product Managers, Engineers, and Data Scientists throughout the product development lifecycle.

• Open Communication: Encouragement of clear, direct, and respectful communication to share ideas, provide feedback, and resolve challenges.

• Iterative Approach: A culture that embraces iteration, learning from feedback, and continuously refining designs based on user input and data.

📝 Enhancement Note: The company culture values a blend of high performance, user-centricity, and collaborative problem-solving, all within an innovative, AI-focused environment. The "ego-less" aspect suggests a team that prioritizes collective goals and mutual respect.

⚡ Challenges & Growth Opportunities

Challenges:

• Simplifying Complexity: The primary challenge is translating the multifaceted, often frustrating, aspects of car ownership (insurance, financing, maintenance, repairs) into a seamless and intuitive user experience.

• AI Integration: Thoughtfully applying AI to enhance user experience without creating complexity or a "black box" effect.

• Scaling Design: Evolving the design system and processes to support rapid company growth and new product initiatives.

• Data Interpretation: Effectively translating complex data and user research into actionable design insights.

Learning & Development Opportunities:

• AI in Design: Deepen understanding and practical application of AI/ML in user experience design.

• Domain Expertise: Become an expert in the automotive, insurance, and fintech sectors, a rapidly evolving and significant market.

• Design System Growth: Contribute to and learn from the development of a scalable design system for a rapidly growing consumer app.

• Strategic Product Influence: Gain experience influencing product strategy at a high-growth, profitable company with ambitious market leadership goals.

📝 Enhancement Note: The challenges are directly tied to the company's mission and the complexity of its domain. The growth opportunities are significant, offering a chance to develop cutting-edge skills in AI-driven design and gain strategic influence in a major market.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to simplify a complex, data-intensive user experience. What was your process, and what was the outcome?" (Focus on your UX thinking, workflow design, and ability to translate complexity.)

• "How do you approach collaborating with Product Managers and Engineers when defining scope and iterating on designs?" (Highlight your communication, negotiation, and iterative process.)

Company & Culture Questions:

• "Why Jerry.ai? What interests you about our mission and our approach to car ownership?" (Research the company's vision, products, and market position.)

• "How do you contribute to a high-craft, collaborative design culture?" (Relate your experiences to Jerry's values of craft, collaboration, and ego-less teamwork.)

Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly present the problem, your role, your process (research, ideation, iteration), the final solution, and the impact (quantified if possible).

• Highlight Key Skills: Explicitly point out how your work demonstrates strong UX thinking, data-informed decisions, and clean UI design.

• Emphasize Problem-Solving: Focus on how you tackled complex challenges and simplified user workflows.

• Be Concise and Engaging: Practice your presentation to be clear, engaging, and within the allotted time. Be prepared for in-depth Q&A.

📝 Enhancement Note: Interview preparation should focus on demonstrating a strong understanding of user-centered design, a data-driven mindset, excellent collaboration skills, and a clear vision for how design can simplify complex experiences, especially within the automotive and fintech space.

📌 Application Steps

To apply for this Sr. Product Designer position:

• Submit your application through the provided link on Ashby.

• Portfolio Customization: Ensure your portfolio prominently features projects that demonstrate strong UX thinking, data-informed decision-making, and clean, intuitive interface design, ideally with examples of simplifying complex experiences.

• Resume Optimization: Tailor your resume to highlight your 5+ years of experience in consumer-facing mobile/web product design, proficiency in Figma, and experience with user flows, wireframing, and prototyping. Quantify achievements where possible.

• Interview Preparation: Practice articulating your design process and rationale for key projects, focusing on how you translate complex requirements into elegant solutions and collaborate with cross-functional teams.

• Company Research: Thoroughly research Jerry.ai's mission, products, target audience, and recent achievements (profitability, funding, customer growth) to articulate your interest and cultural fit.

⚠️ 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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