Staff Product Designer

📍 Job Overview

Job Title: Staff Product Designer Company: Jerry.ai Location: Palo Alto, California, United States (Remote OK) Job Type: Full-Time Category: Product Design / GTM Operations (Design Enablement) Date Posted: February 16, 2026 Experience Level: 10+ Years (Staff Level) Remote Status: Fully Remote (within US, Canada)

🚀 Role Summary

• Spearhead the design vision and execution for core product offerings, including insurance, safety, and repair services, directly impacting millions of car owners.
• Lead 0→1 feature development, transforming complex car ownership tasks into elegant, user-friendly experiences that drive engagement and retention.
• Collaborate intimately with product management, engineering, research, and data science to translate insights into impactful, scalable design solutions.
• Elevate the overall user experience (UX) and visual design quality, focusing on clarity, speed, and craft, to establish Jerry as a trusted digital companion.
• Drive the evolution and maintenance of Jerry's comprehensive design system, ensuring consistency, scalability, and visual excellence across all platforms.

📝 Enhancement Note: This role, while titled "Product Designer," has significant implications for GTM Operations by focusing on the user-facing aspects of a large-scale consumer product. The emphasis on "form" and "craft" for a company with established "function" suggests a crucial period of brand definition and user experience maturation, requiring strong design leadership to translate business success into a best-in-class customer journey. The role's impact on engagement and retention directly influences revenue streams and operational efficiency by reducing churn and increasing customer lifetime value.

📈 Primary Responsibilities

• Lead the end-to-end design process for key product initiatives within Jerry’s ecosystem, encompassing insurance, maintenance, safety, and future car ownership verticals.
• Conceptualize, design, and deliver innovative 0→1 features that address unmet needs in the car ownership market, aiming to modernize and simplify the user experience.
• Forge strong partnerships with Product Managers, Engineers, Researchers, and Data Scientists to identify user pain points, validate design concepts, and ensure data-informed decision-making.
• Develop elegant, intuitive, and frictionless user interfaces and workflows that demonstrably improve user engagement, task completion rates, and customer retention metrics.
• Own the development, maintenance, and adoption of Jerry’s design system, ensuring it is a robust, scalable, and accessible resource for design and development teams.
• Strategically integrate AI capabilities into the user experience to create more personalized, efficient, and proactive car ownership assistance.
• Champion and elevate the standards of UX and visual design across the product portfolio, emphasizing clarity, speed, and meticulous craft in all deliverables.
• Contribute to defining and articulating Jerry's brand story through exceptional design execution and clear communication.

📝 Enhancement Note: The responsibility to "apply AI thoughtfully" suggests a need for designers who can not only conceptualize user flows but also understand how to leverage AI for enhanced personalization and efficiency within a consumer-facing application. This requires a blend of user-centric design principles and an awareness of AI's practical applications in improving customer journeys, which is critical for GTM strategy execution.

🎓 Skills & Qualifications

Education:

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

Experience:

• Minimum of 12 years of progressive experience in product design, with a strong track record of shipping successful consumer-facing products at scale.

Required Skills:

• Exceptional Visual Design: Demonstrated mastery of visual aesthetics, typography, color theory, and layout, capable of creating compelling and on-brand interfaces.
• Thoughtful UX Design: Proven ability to craft intuitive, efficient, and user-centered experiences that solve complex problems for a mass audience.
• Portfolio of Shipped Consumer Products: A robust portfolio showcasing end-to-end design ownership of multiple successful consumer products, preferably at scale.
• Design System Expertise: Experience building, maintaining, and evolving design systems in close collaboration with engineering teams to ensure consistency and scalability.
• 0→1 Feature Development: Proven ability to take ideas from concept through research, ideation, prototyping, user testing, and final launch.
• Cross-functional Collaboration: Excellent communication, presentation, and storytelling skills to effectively align and influence Product Management, Engineering, Research, and Data Science teams.
• Fast-Paced Environment Adaptability: Comfort and proven success in working within agile, fast-paced environments and delivering high-quality work under pressure.
• Mobile and Web Design: Experience designing for both mobile (iOS/Android) and web platforms.

Preferred Skills:

• Experience in marketplaces, fintech, mobility, or insurance industries.
• Familiarity with AI/ML applications in consumer products.
• Experience leading design initiatives and mentoring junior designers.

📝 Enhancement Note: The requirement for 12+ years of experience and the "Staff" title indicate a senior leadership role. The emphasis on "shipping consumer products at scale" and "0→1 feature development" points towards a need for strategic thinking and execution capability, not just execution. The preference for marketplace, fintech, mobility, or insurance experience is crucial for understanding the industry context and potential operational challenges.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrated Impact: Showcase case studies that clearly articulate the problem, your role, the design process, and the measurable business impact (e.g., engagement, retention, conversion improvements) of your shipped products.
• End-to-End Ownership: Provide examples of projects where you led the entire design lifecycle, from initial research and concept exploration to final iteration and launch.
• Design System Contribution: Include examples of your work contributing to or building design systems, highlighting how you ensured consistency and scalability.
• Visual & UX Excellence: Present a range of work that highlights both exceptional visual design craft and deeply thoughtful user experience problem-solving.
• Consumer Product Focus: Prioritize examples of consumer-facing applications, ideally those operating at significant scale.

Process Documentation:

• Evidence of structured design processes, including user research methodologies, ideation techniques, prototyping, and usability testing.
• Examples of how you have collaborated with engineering and product teams to translate design into implemented features.
• Demonstrations of how you iterate on designs based on user feedback, data analytics, and performance metrics.

📝 Enhancement Note: For a Staff-level designer, the portfolio is not just about showcasing visual work but demonstrating strategic thinking, process maturity, and the ability to drive significant business outcomes through design. The expectation is to see a clear narrative of problem-solving, collaboration, and quantifiable results, which directly aligns with GTM operational goals of driving customer acquisition and lifetime value.

💵 Compensation & Benefits

Salary Range: $190,000 - $230,000 USD per year This range is based on the provided information and reflects market rates for a Staff Product Designer in a competitive tech environment. The final salary will be determined by factors such as experience, qualifications, and location.

Benefits:

• Comprehensive Health, Dental, and Vision Coverage
• Generous Paid Time Off (PTO)
• Paid Parental Leave
• 401(K) Retirement Plan with Employer Matching
• Wellness Benefits
• Equity Opportunities (potential for stock options or grants)

Working Hours: 40 hours per week (standard full-time)

📝 Enhancement Note: The salary range is competitive for a Staff Product Designer role in the US tech market. The inclusion of equity opportunities is a significant draw for senior roles, aligning with long-term company growth and employee investment. The comprehensive benefits package supports employee well-being and retention, which are key operational considerations for talent management.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology / Automotive / Fintech / Insurance Company Size: Estimated 50-200 employees (based on funding and growth trajectory, though not explicitly stated) Founded: 2017

Team Structure:

• The design team is led by Kruise Sapstein, Head of Design, focusing on building a high-craft, high-performing design culture.
• You will report directly to the Head of Design, with significant collaboration across a product organization of 11 Product Managers, 55 Engineers, and 12 Analysts/Data Scientists.
• This structure indicates a highly collaborative, product-centric environment where design is integrated early and often into the development process.

Methodology:

• Data-driven decision-making is a core tenet, with a strong emphasis on leveraging insights from 12 Analysts/Data Scientists.
• Agile development methodologies are implied by the fast-paced environment and cross-functional collaboration.
• A focus on applying AI and ML to enhance customer experience is central to Jerry's product strategy.

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

📝 Enhancement Note: Jerry.ai operates in a dynamic intersection of automotive, insurance, and fintech, leveraging AI to simplify car ownership. The company's rapid growth (over 5 million customers, profitability, significant funding) suggests a culture that values innovation, speed, and customer focus. The relatively lean design team structure for a company of this scale implies a high degree of autonomy and impact for senior designers.

📈 Career & Growth Analysis

Operations Career Level: Staff Product Designer This is a senior individual contributor role, expected to provide design leadership, mentor others, and drive significant strategic initiatives. It's a critical role for defining and scaling the user experience as the company grows towards its $10B valuation goal.

Reporting Structure:

• Reports directly to the Head of Design.
• Works closely with Product Managers, Engineers, and Data Scientists.
• Expected to influence design direction and quality across multiple product areas.

Operations Impact:

• Directly influences customer acquisition, engagement, and retention through superior user experience design, impacting revenue growth and operational efficiency.
• Shapes the brand perception and user trust, crucial for a company managing sensitive financial and logistical aspects of car ownership.
• Contributes to the development of scalable design systems and processes, enhancing engineering efficiency and product consistency.

Growth Opportunities:

• Design Leadership: Potential to grow into a Group Design Lead or Director role as the design team expands.
• Strategic Influence: Opportunity to shape product strategy and company direction through design insights and advocacy.
• Skill Specialization: Deepen expertise in AI-driven design, consumer marketplaces, or fintech product development.
• Mentorship: Guide and mentor junior designers, contributing to the growth of the design team and fostering a strong design culture.

📝 Enhancement Note: The "Staff" level implies a significant opportunity for growth beyond individual contribution, into leadership, mentorship, and strategic product influence. This role is pivotal for a company aiming for massive scale, requiring a designer who can not only execute but also guide and elevate the entire design function.

🌐 Work Environment

Office Type: Remote-First Company with a strong emphasis on distributed collaboration. Office Location(s): While headquarters are in Palo Alto, CA, the company fully supports remote work across the United States and Canada. Specific hubs may exist, but the primary mode is remote.

Workspace Context:

• Collaborative Remote Culture: Expect a high degree of virtual collaboration using tools like Slack, Zoom, and potentially Figma for real-time design work.
• Tooling: Access to industry-standard design and prototyping tools, integrated with engineering workflows.
• Cross-functional Interaction: Frequent opportunities to interact with product, engineering, and data teams, fostering a holistic understanding of product development.

Work Schedule:

• Standard 40-hour work week, with flexibility often afforded to remote employees.
• Emphasis on asynchronous communication where possible, balanced with synchronous meetings for critical discussions and collaborations.

📝 Enhancement Note: As a remote-first company, Jerry.ai likely has mature processes for remote collaboration and asynchronous work. This environment requires strong self-discipline, proactive communication, and comfort with digital collaboration tools, which are essential for operational efficiency in a distributed team.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Review of resume and portfolio to assess qualifications and alignment with the role.
• Portfolio Presentation: A deep dive into selected case studies from your portfolio, discussing your process, impact, and role. Expect to articulate your design decisions and their outcomes.
• Cross-functional Interviews: Meetings with Product Managers, Engineers, and potentially Data Scientists to assess collaboration style, technical understanding, and ability to work with diverse teams.
• Design Challenge/Workshop: Potentially a take-home assignment or a live design workshop to evaluate your problem-solving skills, design thinking, and ability to articulate solutions under pressure.
• Hiring Manager Interview: Final discussion with the Head of Design to assess cultural fit, leadership potential, and strategic alignment.

Portfolio Review Tips:

• Tell a Story: Structure your case studies as narratives – problem, your approach, your solution, and the results. Focus on the "why" behind your decisions.
• Quantify Impact: Whenever possible, use data and metrics to demonstrate the success of your designs. Show how you drove engagement, retention, or other key business objectives.
• Showcase Process: Don't just show final screens. Include wireframes, user flows, research insights, and iterations to demonstrate your thought process.
• Highlight Collaboration: Mention how you worked with PMs, engineers, and data scientists. Emphasize your ability to influence and align stakeholders.
• Tailor to Jerry: Demonstrate an understanding of Jerry's mission and target audience. If possible, include work that shows relevant experience (consumer apps, marketplaces, fintech).

Challenge Preparation:

• Anticipate challenges that involve simplifying complex user journeys, integrating AI features, or improving engagement/retention in a consumer app context.
• Practice articulating your design rationale clearly and concisely, especially when under time constraints.
• Be prepared to discuss how you would approach designing for scale and maintaining consistency through a design system.

📝 Enhancement Note: The interview process for a Staff Designer will be rigorous, focusing on strategic impact, leadership potential, and deep design craft. A strong portfolio that showcases quantifiable results and a clear design process is paramount. The emphasis on collaboration and influencing cross-functional teams is a key indicator of the operational dynamics within Jerry.ai.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (highly likely, given industry trends and collaborative focus), Sketch, Adobe Creative Suite.
• Design System Management: Tools integrated with Figma/Sketch, potentially Storybook for component documentation.
• Collaboration: Slack, Zoom, Google Workspace/Microsoft 365.

Analytics & Reporting:

• Tools like Amplitude, Mixpanel, Google Analytics, Tableau, or Looker for user behavior analysis and performance tracking.
• Understanding of how to interpret data to inform design decisions is critical.

CRM & Automation:

• While not a direct design tool, understanding how CRM data (e.g., Salesforce, HubSpot) and marketing automation platforms influence customer journeys can be beneficial.

📝 Enhancement Note: Proficiency with Figma is almost a given for this role. The ability to leverage analytics tools to inform design decisions and understand the impact of design on key business metrics (engagement, retention) is crucial for demonstrating operational value.

👥 Team Culture & Values

Operations Values:

• Customer Obsession: A deep commitment to understanding and serving the needs of car owners, making their lives easier and more affordable.
• Craftsmanship & Quality: A high regard for the quality of design, code, and overall product execution.
• Data-Driven Innovation: Utilizing data and AI to inform product development and create intelligent solutions.
• Speed & Agility: A culture that embraces rapid iteration and quick decision-making in a fast-paced market.
• Collaboration & Ego-lessness: Working effectively across teams, valuing collective success over individual accolades.

Collaboration Style:

• Highly collaborative, with design integrated into product teams from the outset.
• Emphasis on clear communication, constructive feedback, and shared ownership of product success.
• Expectation of proactive engagement and contribution from all team members, regardless of role.

📝 Enhancement Note: The emphasis on "craft," "speed," and "collaboration" points to a culture that values both high-quality execution and efficient, team-oriented workflows. Understanding these values will be key to cultural fit and successful integration into the team.

⚡ Challenges & Growth Opportunities

Challenges:

• Scaling Design: Ensuring design quality and consistency across a rapidly growing product and user base.
• Simplifying Complexity: Designing intuitive solutions for the often complex and fragmented car ownership lifecycle.
• AI Integration: Effectively and ethically integrating AI features to enhance, not complicate, the user experience.
• Balancing Speed and Craft: Maintaining high design standards while operating in a fast-paced, iterative environment.

Learning & Development Opportunities:

• Industry Conferences: Potential to attend leading design and tech conferences.
• Skill Advancement: Opportunities to deepen expertise in AI-driven design, consumer marketplace dynamics, and user research.
• Mentorship: Direct mentorship from the Head of Design and exposure to executive leadership.
• Impactful Projects: Work on mission-critical features that directly contribute to the company's ambitious growth targets.

📝 Enhancement Note: The challenges highlight opportunities for a designer to make a significant impact by solving complex problems related to scale, user experience, and emerging technologies like AI. The growth opportunities are substantial for a senior individual contributor looking to influence product strategy and design leadership.

💡 Interview Preparation

Strategy Questions:

• "How would you approach designing a new feature for car insurance renewal that leverages AI to personalize the user's experience and potentially offer cost savings?"
• "Describe a time you had to balance aggressive timelines with maintaining high design quality. What was your approach?"
• "How would you approach building or evolving a design system to support a rapidly growing product suite?"
• "Walk us through a project where you used data and user research to significantly influence product direction."

Company & Culture Questions:

• "What interests you most about Jerry's mission and the car ownership space?"
• "How do you approach collaborating with product managers and engineers who may have different priorities?"
• "Describe your ideal design team culture. How do you contribute to a positive and productive team environment?"
• "How do you measure the success of your design work beyond visual appeal?"

Portfolio Presentation Strategy:

• Focus on Impact: For each case study, clearly articulate the business problem, your unique contribution, the design process, and the quantifiable results achieved.
• Demonstrate Strategic Thinking: Explain the "why" behind your design decisions, linking them to user needs and business objectives.
• Showcase Collaboration: Highlight how you worked with cross-functional teams and influenced outcomes.
• Be Prepared for Deep Dives: Expect questions about specific design choices, trade-offs made, and alternative solutions considered.
• Articulate Your Vision: Be ready to discuss your perspective on the future of product design in the automotive/fintech space and how AI can play a role.

📝 Enhancement Note: Prepare to discuss your experience with scalability, AI integration, and driving measurable business outcomes. Your ability to articulate your design process, rationale, and collaborative approach will be critical. Demonstrating an understanding of Jerry's market and mission will be highly advantageous.

📌 Application Steps

To apply for this Staff Product Designer position:

• Submit your application through the provided link on Ashby.
• Tailor Your Resume: Highlight your 12+ years of experience, focus on shipped consumer products at scale, and emphasize end-to-end project ownership and design system contributions. Use keywords from the job description.
• Curate Your Portfolio: Select 3-5 of your strongest case studies that demonstrate exceptional visual design, thoughtful UX, and measurable impact. Prioritize consumer products and showcase your process clearly. Ensure your portfolio is easily accessible online.
• Prepare Your Narrative: Practice articulating your portfolio case studies, focusing on the problem, your solution, your role, and the quantifiable results. Be ready to discuss your experience with AI, design systems, and cross-functional collaboration.
• Research Jerry.ai: Understand their mission, product offerings, recent news, and company culture to articulate your interest and fit during interviews.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.

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