Staff Product Designer

📍 Job Overview

Job Title: Staff Product Designer
Company: Jerry.ai
Location: San Francisco, California, United States
Job Type: FULL_TIME
Category: Product Design / GTM Operations
Date Posted: 2025-10-20
Experience Level: Mid-Senior Level (2-5 years estimated)
Remote Status: Fully Remote (within the United States)

🚀 Role Summary

• Drive measurable improvements in user engagement and onboarding for Jerry's core car ownership services (insurance shopping, safety, repairs) through user-centric design.
• Lead the development of 0→1 features that modernize car care for everyday consumers, directly impacting product strategy and user experience.
• Conduct comprehensive user research (qualitative and quantitative), rapid prototyping in Figma, and validate design solutions through usability testing and A/B experiments.
• Elevate the overall UX quality of Jerry's products, focusing on clarity, speed, and design consistency across all touchpoints.
• Strategically integrate AI to enhance product speed, clarity, and user helpfulness, aligning with Jerry's AI-powered mission.

📝 Enhancement Note: While the title is "Staff Product Designer," the responsibilities clearly indicate a significant impact on Go-To-Market (GTM) strategy through user engagement and onboarding. The role's focus on driving "measurable gains" and "shipping 0→1 features" with a data-driven approach (user research, A/B testing) aligns with GTM operations principles of optimizing the customer journey and product adoption. The emphasis on "delightful, friction-less experiences" is key to successful GTM execution in consumer products.

📈 Primary Responsibilities

• Design and iterate on user flows and interfaces for Jerry's suite of car ownership products, ensuring a seamless and intuitive user experience from initial engagement through ongoing use.
• Collaborate closely with Product Managers, Engineers, and Data Scientists to translate business requirements and user needs into high-fidelity designs and functional prototypes.
• Champion user research initiatives, including planning, conducting, and synthesizing findings from user interviews, surveys, and usability tests to inform design decisions.
• Develop and maintain a robust design system and style guide to ensure brand consistency, scalability, and efficiency in design and development processes.
• Craft compelling visual designs that enhance brand perception and user trust, aligning with Jerry's vision of being a "trusted friend in your pocket."
• Contribute to product strategy by identifying opportunities for innovation and improvement based on user insights, market trends, and competitive analysis.
• Advocate for design best practices within the product organization, fostering a culture of design excellence and user-centricity.
• Apply AI principles and technologies to create intelligent, personalized user experiences that simplify complex car ownership tasks.

📝 Enhancement Note: The core responsibilities highlight a blend of strategic product design and tactical execution, crucial for GTM success. The emphasis on "measurable gains," "0→1 features," and "A/B experiments" points to a data-driven approach that directly supports GTM objectives like user acquisition, conversion, and retention. The need to "raise the UX quality bar" suggests a focus on optimizing the customer journey post-acquisition to improve overall lifetime value.

🎓 Skills & Qualifications

Education: Bachelor's degree in Design, Human-Computer Interaction, or a related field, or equivalent practical experience.
Experience: 2-5 years of professional experience in Product Design, with a proven track record of shipping consumer-facing digital products.

Required Skills:

• Portfolio: A strong portfolio demonstrating exceptional visual taste, thoughtful UX design, and successfully shipped consumer-facing products. This is a critical requirement for evaluating design capabilities and impact.
• User Research: Proficiency in conducting qualitative and quantitative user research, including user interviews, surveys, and usability testing.
• Prototyping: Advanced skills in rapid prototyping using tools like Figma, enabling quick iteration and validation of design concepts.
• UX/UI Design: Deep understanding of user-centered design principles, interaction design, information architecture, and visual design best practices.
• Collaboration: Demonstrated ability to work effectively with cross-functional teams, including product managers, engineers, and data scientists, fostering strong working relationships and driving consensus.
• Problem-Solving: Capacity to break down complex problems into simple, clear, and trustworthy design solutions.
• Agile Development: Experience working within agile development environments and collaborating with engineering teams to ship products efficiently.
• Design Systems: Familiarity with creating and utilizing design systems to ensure consistency and scalability.

Preferred Skills:

• Experience in marketplace, fintech, mobility, or other complex consumer applications.
• Familiarity with AI/ML concepts and their application in user experience design.
• Experience with A/B testing and data analysis to inform design decisions.
• A passion for the automotive industry or a strong understanding of car ownership challenges.

📝 Enhancement Note: The emphasis on a "portfolio that demonstrates strong visual taste, thoughtful UX, and shipped work in consumer-facing products" is a direct indicator of the company's need for designers who can translate strategy into tangible, user-friendly products. The requirement to "break down complexity" and design "simple, clear, and trustworthy" flows is essential for a company aiming to simplify a complex domain like car ownership. Experience in marketplaces and fintech is a bonus, suggesting that the company values designers who can navigate complex transaction and data management scenarios.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Shipped Products: Showcase 2-3 key projects that have been successfully launched and are currently in market, with clear indicators of user impact or business results.
• User-Centered Design Process: Detail your end-to-end design process for at least one major project, highlighting how you used user research, ideation, prototyping, testing, and iteration to arrive at the final solution.
• Visual Design & UI: Present examples of your visual design skills, demonstrating strong typography, color theory, layout, and brand consistency.
• Interaction Design: Include examples of complex user flows you've designed, illustrating your ability to create intuitive and efficient interactions.
• Problem/Solution Framing: Clearly articulate the user problem or business challenge addressed by each project and how your design solution effectively resolved it.

Process Documentation:

• Research Synthesis: Demonstrate how you synthesize qualitative and quantitative user research findings into actionable design insights and recommendations.
• Prototyping & Testing: Provide examples of how you've used prototyping tools (e.g., Figma) to test design hypotheses and gather user feedback, and how that feedback influenced design iterations.
• Collaboration & Handoff: Illustrate your process for collaborating with engineers and product managers, including design handoff documentation and communication strategies.
• Metrics & Impact: Where possible, quantify the impact of your designs using relevant metrics (e.g., increased engagement, improved conversion rates, reduced task completion time).

📝 Enhancement Note: The portfolio requirements are heavily focused on demonstrating a proven design process that leads to tangible results. This aligns with GTM operations' need for designers who can not only create aesthetically pleasing interfaces but also drive measurable business outcomes through user engagement and conversion optimization. The emphasis on "shipped work" and "quantifiable impact" is critical for assessing a candidate's ability to contribute to GTM success.

💵 COMPENSATION & BENEFITS

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

Benefits:

• Comprehensive health, dental, and vision coverage.
• Generous paid time off (PTO) policy.
• Paid parental leave for new parents.
• 401(K) plan with employer matching contributions to support retirement savings.
• Wellness benefits designed to support employee well-being.
• Opportunities for equity grants, providing a stake in the company's success.

Working Hours: 40 hours per week (standard full-time). While the role is remote, a commitment to timely communication and collaboration during core business hours (likely Pacific Time, given the San Francisco HQ) is expected to facilitate effective teamwork with engineering and product teams.

📝 Enhancement Note: The salary range provided ($150,000 - $200,000 USD) is competitive for a Staff Product Designer role in a high-cost-of-living area like San Francisco, even for a remote position within the US. The inclusion of equity opportunities is a significant draw for senior roles, aligning with the "Staff" level designation and indicating potential for substantial long-term rewards. The note on working hours emphasizes the need for collaboration, which is crucial for GTM alignment even in a remote setting.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology (specifically AI-powered consumer automotive services). Jerry.ai operates at the intersection of AI, automotive, insurance, and fintech, aiming to disrupt the $2T car ownership market. This dynamic industry requires agility and innovation.
Company Size: Jerry.ai has grown significantly, with a product organization comprising 11 product managers, 55 engineers, and 12 product analysts/data scientists. While the exact total company size isn't explicitly stated, this indicates a well-established, mid-to-large sized tech company with a substantial product development team.
Founded: Founded in 2017, Jerry.ai has a history of innovation and growth, having reached profitability in 2024 and aiming for significant future valuation. This provides a context of a company that has moved beyond the startup phase and is focused on scaling and market expansion.

Team Structure:

• The design team is currently small, with the Staff Product Designer reporting directly to the CEO & Head of Product (Art Agrawal) until a Head of Design is hired. This offers significant influence and direct access to leadership.
• The designer will work closely with the Founding Designer (Patrick Westwood), providing a bridge to existing design knowledge and practices.
• The broader product organization is robust, with ample collaboration opportunities with Product Managers, Engineers, and Data Scientists, fostering a cross-functional, product-led environment.

Methodology:

• Data-Driven Product Development: The company emphasizes data science and analytics, with 12 product analysts/data scientists on the team, indicating a strong focus on using data to inform product decisions and measure impact.
• AI Integration: A core part of Jerry's strategy is the application of AI and machine learning to simplify car ownership, suggesting a culture that embraces cutting-edge technology.
• User-Centricity: The role's description emphasizes creating "delightful, friction-less experiences" and raising the "UX quality bar," pointing to a deep commitment to understanding and serving user needs.

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

📝 Enhancement Note: The company's focus on a $2T market and its AI-first approach positions it as a significant player in the automotive tech space. The team structure, with direct reporting to the CEO and close collaboration with a large engineering and product team, suggests a high-impact role where design decisions can significantly influence company trajectory. The emphasis on data and AI aligns with modern GTM operations, where data-driven insights and technological leverage are paramount.

📈 Career & Growth Analysis

Operations Career Level: This role is designated as "Staff Product Designer," indicating a senior individual contributor position. It signifies a level of expertise and autonomy where the designer is expected to lead complex projects, mentor junior designers (when they join), and significantly influence product strategy and design standards. This level typically requires 5-10 years of experience, though the listed requirement is 2-5 years, suggesting that exceptional talent and a strong portfolio can accelerate career progression.

Reporting Structure: Initially, the Staff Product Designer will report directly to the CEO & Head of Product, Art Agrawal. This direct line of communication provides immense visibility and influence. The role will transition to reporting to a future Head of Design, suggesting a growth path for design leadership within the organization. Collaboration will be extensive with Product Managers, Engineers, and Data Scientists.

Operations Impact: The Staff Product Designer's work will directly shape the user experience of Jerry's AI-powered car ownership platform. This includes driving user engagement and onboarding, launching new features, and improving overall UX quality. These elements are critical for GTM success, directly impacting customer acquisition, retention, and the perceived value of Jerry's services. By making car ownership "accessible and affordable," the designer contributes to the company's mission and its ability to capture significant market share.

Growth Opportunities:

• Design Leadership: As one of the early designers, there is a clear opportunity to shape the future design team, potentially leading to a Head of Design role as the company scales.
• Product Strategy Influence: Direct access to the CEO and a senior role position the designer to have a significant impact on product strategy and roadmap decisions.
• Skill Development: Working with AI, complex consumer applications, and a data-rich environment offers opportunities to deepen expertise in cutting-edge design challenges.
• Cross-Functional Expertise: Deep collaboration across product, engineering, and data science will foster a holistic understanding of product development and GTM execution.
• Equity and Financial Growth: The potential for equity grants aligns career growth with company success, offering significant financial upside.

📝 Enhancement Note: The "Staff" title, coupled with the reporting structure to the CEO, indicates a high-impact, high-visibility role. The growth opportunities are significant, particularly in shaping the design function and influencing product strategy, which are key aspects of driving GTM success from a product design perspective. The emphasis on AI and complex consumer applications positions this role for significant skill development relevant to future GTM challenges.

🌐 Work Environment

Office Type: The role is advertised as "Fully Remote" within the United States, with a San Francisco, California headquarters. This indicates a remote-first or remote-friendly culture that prioritizes talent over location.
Office Location(s): While the company is headquartered in San Francisco, CA, the remote nature of the role means employees can be based anywhere within the United States. This offers flexibility and access to a wider talent pool.

Workspace Context:

• Remote Collaboration: The work environment will be heavily reliant on digital collaboration tools (e.g., Slack, Figma, Zoom, project management software) to maintain communication and productivity across distributed teams.
• Cross-Functional Interaction: Designers will work closely with a large cohort of engineers, product managers, and data scientists, fostering a collaborative and iterative product development process.
• Impactful Design: The environment is geared towards building a "disruptive" product, suggesting a fast-paced, results-oriented atmosphere where design directly contributes to business objectives.

Work Schedule: Standard full-time (40 hours per week). While remote, effective collaboration will require responsiveness and availability during core business hours, likely aligned with Pacific Time to sync with the San Francisco-based HQ and product teams. This ensures seamless integration with engineering and product sprints.

📝 Enhancement Note: The fully remote nature of the role requires strong self-discipline and excellent communication skills. The emphasis on collaboration with a large product and engineering team suggests a structured, yet dynamic, remote work environment where designers are integrated into the core product development lifecycle. This integration is vital for ensuring design outputs effectively support GTM initiatives.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio to assess qualifications and alignment with the role's requirements.
• Portfolio Presentation & Discussion: Candidates will likely present their portfolio, discussing specific projects, design process, and impact. This stage will focus on visual taste, UX thinking, and problem-solving abilities.
• Take-Home Challenge or Design Exercise: A practical exercise to evaluate design skills, problem-solving approach, and ability to work within constraints. This might involve designing a specific feature or flow.
• Cross-Functional Interviews: Meetings with Product Managers, Engineers, and potentially Data Scientists to assess collaboration skills, technical understanding, and cultural fit.
• Final Interview: Likely with the CEO & Head of Product (Art Agrawal) to discuss strategic alignment, vision, and overall fit for the company and the role.

Portfolio Review Tips:

• Structure for Impact: Organize your portfolio to clearly articulate the problem, your role, your process, the solution, and the measurable impact of your work. Use the STAR method (Situation, Task, Action, Result) as a guide.
• Show, Don't Just Tell: Use high-fidelity mockups, interactive prototypes, and user flow diagrams to visually demonstrate your design capabilities.
• Highlight Data & Research: Emphasize instances where user research and data (qualitative and quantitative) informed your design decisions. Explain how you used testing and A/B experiments to validate solutions.
• Tailor to Jerry: Research Jerry's products and mission. Highlight projects that showcase your ability to design for complex consumer applications, marketplaces, or AI-driven features.
• Be Ready to Discuss: Prepare to talk in detail about your decision-making process, trade-offs you made, and the outcomes of your projects.

Challenge Preparation:

• Understand the Context: If given a take-home challenge, thoroughly understand the problem statement and the target user.
• Prioritize and Scope: Focus on delivering a well-reasoned solution within the given time constraints. It's better to deliver a focused, high-quality solution than a broad, unfinished one.
• Communicate Your Assumptions: Clearly state any assumptions you make during the challenge, especially regarding user needs or business goals.
• Design for Iteration: Show that you've considered future iterations and potential improvements beyond the immediate scope of the challenge.

📝 Enhancement Note: The interview process is designed to thoroughly assess a candidate's design acumen, problem-solving skills, and ability to collaborate effectively within a product team. The emphasis on portfolio review and a potential design challenge highlights the company's focus on practical skills and demonstrable impact, which are critical for GTM success.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Essential for design, prototyping, and collaboration. Proficiency in Figma is a key requirement.
• Prototyping Tools: Beyond Figma, familiarity with other prototyping tools may be beneficial for quick concept validation.
• User Research Platforms: Tools for conducting user interviews, surveys, and usability testing (e.g., UserTesting.com, Lookback, SurveyMonkey).
• Collaboration Tools: Slack for real-time communication, Jira/Asana for project management, Confluence for documentation.

Analytics & Reporting:

• A/B Testing Platforms: Experience with tools that facilitate experimentation to measure design impact (e.g., Optimizely, VWO, or in-house solutions).
• Analytics Tools: Familiarity with platforms like Google Analytics, Mixpanel, Amplitude, or similar tools to understand user behavior and measure engagement metrics.
• Data Visualization Tools: Potentially exposure to tools used by data scientists for reporting and analysis.

CRM & Automation:

• While not directly a designer's tool, understanding how design impacts the user journey through CRM and marketing automation platforms can be beneficial for GTM alignment.

📝 Enhancement Note: The explicit mention of Figma as a primary tool is crucial. Proficiency in analytics and A/B testing tools is also highlighted, underscoring the data-driven nature of the role and its contribution to GTM optimization. A designer who understands how their work impacts conversion funnels and user engagement metrics will be highly valuable.

👥 Team Culture & Values

Operations Values:

• User-Centricity: A deep commitment to understanding and solving user problems, ensuring that design decisions are always grounded in user needs and feedback.
• Data-Driven Decision Making: Valuing insights derived from user research and analytics to guide product development and design iterations, ensuring effectiveness and impact.
• Collaboration & Transparency: Fostering an open environment where ideas are shared freely, feedback is constructive, and teams work together seamlessly towards common goals.
• Efficiency & Speed: A focus on delivering high-quality work efficiently, embracing agile methodologies to iterate quickly and adapt to market changes.
• Innovation & AI Integration: Embracing new technologies, particularly AI, to create novel solutions and push the boundaries of what's possible in car ownership services.

Collaboration Style:

• Cross-Functional Partnership: The design team is deeply embedded within the product organization, working hand-in-hand with Product Managers, Engineers, and Data Scientists. This ensures design is integrated from ideation through development.
• Constructive Feedback: A culture that encourages open and honest feedback to elevate the quality of work and foster continuous improvement.
• Shared Ownership: A sense of collective responsibility for product success, where all team members contribute to creating the best possible user experience and business outcomes.

📝 Enhancement Note: The emphasis on data-driven decision-making, collaboration, and efficiency directly aligns with the principles of GTM operations. A designer who thrives in this environment will be well-positioned to contribute to the strategic goals of user acquisition, engagement, and retention.

⚡ Challenges & Growth Opportunities

Challenges:

• Scaling Design: As one of the first designers, building out design processes and standards for a rapidly growing company presents a significant challenge and opportunity.
• Simplifying Complexity: Designing intuitive experiences for a highly complex domain (car ownership, insurance, financing) requires innovative problem-solving.
• AI Integration: Effectively leveraging AI to enhance user experience without creating confusion or over-complication.
• Remote Collaboration: Managing effective design collaboration and communication within a distributed team.
• Balancing Vision and Execution: Aligning ambitious product vision with the practicalities of rapid development and shipping.

Learning & Development Opportunities:

• Leadership Development: Opportunity to shape the design function and potentially lead a team as Jerry grows.
• AI in Design: Deep dive into applying AI/ML to consumer products, a highly in-demand skill.
• Complex Domain Expertise: Gaining in-depth knowledge of the automotive, insurance, and fintech industries.
• Strategic Product Influence: Direct exposure to executive-level product strategy and decision-making.
• Industry Participation: Potential to attend industry conferences or pursue certifications related to product design, AI, or UX.

📝 Enhancement Note: The challenges listed highlight the significant impact and learning potential of this role. Tackling the complexity of car ownership and integrating AI are key areas where a designer can grow and contribute exceptionally to GTM strategy by improving user adoption and retention.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you used user research to significantly alter a product's direction or design. What was the outcome?" (Focus on process, data interpretation, and impact.)
• "How would you approach designing a new AI-powered feature for car maintenance reminders to ensure it's both helpful and trustworthy for users?" (Focus on AI ethics, user trust, and clarity.)
• "Walk me through your process for designing a complex user flow, from initial concept to final shipped product. What trade-offs did you consider?" (Focus on design methodology, problem-solving, and iteration.)

Company & Culture Questions:

• "What excites you about Jerry's mission to simplify car ownership, and how do you see design playing a role in achieving it?" (Demonstrate understanding of the company's value proposition and your contribution to GTM.)
• "How do you ensure design consistency and quality across a product, especially when working with a growing and distributed team?" (Highlight your approach to design systems and collaboration.)
• "How do you measure the success of your designs, and what metrics do you prioritize for consumer-facing products?" (Showcase your data-driven mindset and understanding of user engagement/conversion.)

Portfolio Presentation Strategy:

• Craft a Narrative: For each project, tell a clear story about the problem, your specific contributions, the challenges you faced, your design decisions, and the quantifiable results.
• Focus on Impact: Emphasize the "why" and the "what happened next" for each project, ensuring you highlight how your design work drove user engagement, solved user problems, or achieved business goals.
• Showcase Your Process: Demonstrate your thinking from research and ideation through to detailed UI and testing.
• Be Ready for Deep Dives: Anticipate detailed questions about your design choices, technical constraints, and collaboration experiences.

📝 Enhancement Note: Preparing for these types of questions will require candidates to connect their design experience directly to business outcomes and GTM objectives. Demonstrating an understanding of how design drives user acquisition, engagement, and retention will be key to success.

📌 Application Steps

To apply for this Staff Product Designer position:

• Submit your application through the provided link on Ashby.
• Portfolio Optimization: Ensure your portfolio clearly highlights consumer-facing products, your end-to-end design process, and quantifiable results. Tailor your case studies to showcase experience with complex applications or AI-driven features if possible.
• Resume Alignment: Update your resume to emphasize achievements related to user engagement, onboarding, feature development, and collaboration with product and engineering teams. Use keywords from the job description like "user research," "prototyping," "Figma," and "consumer apps."
• Prepare Your Narrative: Practice articulating your design process and project outcomes concisely and impactfully. Be ready to discuss your portfolio in detail and answer strategic questions about design's role in business success.
• Research Jerry.ai: Familiarize yourself with Jerry's mission, products, and recent news. Understand their AI-first approach and their goal of simplifying car ownership. This will help you tailor your responses and demonstrate genuine interest.

⚠️ 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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