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

Date Posted: May 18, 2026

Experience Level: Senior (12+ years)

Remote Status: Fully Remote (US & Canada)

🚀 Role Summary

• Spearhead the design of core product offerings within the car ownership ecosystem, focusing on insurance, safety, and repair services.

• Drive the creation of innovative 0→1 features that modernize and simplify car ownership for a mass consumer audience.

• Collaborate closely with product management, engineering, and data science teams to translate user insights and business objectives into impactful design solutions.

• Develop and maintain a robust design system, ensuring scalability, consistency, and visual excellence across all Jerry.ai products.

• Leverage AI capabilities to enhance user experience, making it faster, more personalized, and intuitive for millions of car owners.

📝 Enhancement Note: While the title is "Staff Product Designer," the responsibilities and emphasis on driving product strategy, cross-functional collaboration, and GTM impact align closely with roles that operate at the intersection of product development and Go-to-Market (GTM) operations. This role requires a strong understanding of how design contributes to user acquisition, engagement, and retention, which are key GTM metrics.

📈 Primary Responsibilities

• Lead the end-to-end design process for critical product initiatives within Jerry’s core verticals, including car insurance, safety features, and repair services.

• Conceptualize and deliver groundbreaking 0→1 features that address unmet needs in the car ownership market, aiming to redefine the consumer experience.

• Partner with User Research, Product Management, and Data Science teams to identify user pain points, market opportunities, and strategic priorities, translating findings into compelling design strategies.

• Craft elegant, intuitive, and frictionless user experiences that demonstrably improve user engagement and long-term retention rates.

• Own the development and continuous evolution of Jerry's comprehensive design system, ensuring its adoption and application for consistent, scalable, and high-quality design outcomes.

• Strategically integrate AI and machine learning functionalities into product design to create more intelligent, responsive, and personalized user journeys.

• Elevate the overall quality of UX and visual design, focusing on clarity, speed of interaction, and meticulous craft to set new industry standards.

📝 Enhancement Note: The emphasis on "0→1 features," "measurable gains in engagement and retention," and "applying AI to make our experience faster, clearer, and more personal" strongly indicates a focus on GTM impact. The role is expected to not only create beautiful interfaces but also to drive business outcomes through design, making it relevant to GTM operations professionals who understand the interplay between product experience and market success.

🎓 Skills & Qualifications

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

Experience: 12+ years of progressive experience in product design, with a significant portion in in-house roles or at design agencies, focusing on shipping consumer-facing products.

Required Skills:

• A strong portfolio showcasing exceptional visual design, profound UX thinking, and successful shipping of consumer products at scale.

• Proven track record of owning design projects from inception (research, concept) through to launch and iterative refinement.

• Demonstrated experience in building, maintaining, and evolving design systems in close collaboration with engineering teams.

• Adaptability and effectiveness in fast-paced, dynamic environments, with a consistent ability to deliver high-quality work rapidly.

• Excellent communication, presentation, and storytelling skills, essential for aligning diverse cross-functional teams and stakeholders.

Preferred Skills:

• Experience within marketplaces, fintech, mobility, or the insurance industry.

• Familiarity with AI/ML integration in product design.

• Expertise in mobile-first design principles and responsive web design.

• Experience with user research methodologies and usability testing.

📝 Enhancement Note: The "12+ years" requirement signifies a senior or staff-level individual contributor role. The emphasis on "shipping consumer products at scale" and "end-to-end ownership" points to a need for pragmatic design execution that directly impacts user acquisition and retention, aligning with GTM objectives. The preferred experience in marketplaces, fintech, mobility, or insurance is highly relevant for understanding the business context and customer segments Jerry.ai serves, critical for effective GTM strategy.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase a minimum of 3-5 significant projects that demonstrate end-to-end product design ownership, from initial concept and user research to final shipped product and iteration.

• Highlight case studies with a clear narrative arc, detailing the problem, your role, the design process, key decisions, and quantifiable outcomes (e.g., improvements in engagement, retention, conversion rates).

• Include examples of how you’ve collaborated with engineering to build and maintain design systems, demonstrating an understanding of scalability and consistency.

• Present work that clearly articulates the application of UX principles, visual design craft, and user-centered problem-solving.

Process Documentation:

• Provide evidence of your systematic approach to design, including user research methodologies, ideation processes, wireframing, prototyping, and usability testing.

• Demonstrate how you’ve contributed to or led the development of design system components, including style guides, UI patterns, and asset libraries.

• Showcase your ability to document design decisions and rationale, facilitating clear communication with product managers, engineers, and other stakeholders.

• Illustrate how you measure the impact of your design solutions, referencing metrics related to user behavior, engagement, and business goals.

📝 Enhancement Note: The explicit requirement for a portfolio demonstrating "shipped consumer products at scale" and "end-to-end project ownership" is a strong indicator that candidates will be evaluated on their ability to deliver tangible results. For a GTM-focused role, this means showcasing how design directly contributes to user acquisition, conversion, and retention metrics. The emphasis on design systems also highlights the need for operational efficiency in design execution.

💵 Compensation & Benefits

Salary Range: $190,000 - $230,000 USD per year.

Benefits:

• Comprehensive health, dental, and vision insurance coverage.

• Generous paid time off (PTO) policy.

• Paid parental leave.

• 401(K) plan with employer matching.

• RRSP plan with employer matching (for Canadian employees).

• Wellness benefits.

• Stock options and equity grants, offering ownership in Jerry.ai's growth.

Working Hours: Standard full-time hours, typically 40 hours per week, with flexibility expected for project deadlines and cross-functional collaboration across different time zones.

📝 Enhancement Note: The salary range provided is competitive for a Staff-level Product Designer in the US tech market, particularly in regions like Palo Alto, CA, though the remote status may influence this slightly depending on the candidate's specific location. The inclusion of equity grants and options is common for senior roles in growth-stage startups and is a significant component of total compensation, aligning with the company's ambitious growth targets. The mention of both 401(K) and RRSP plans indicates a commitment to supporting employees in both the US and Canada.

🎯 Team & Company Context

🏢 Company Culture

Industry: Insurtech, Automotive Technology, AI, Consumer Technology. Jerry.ai operates at the intersection of these dynamic sectors, aiming to disrupt the $2T car ownership market with an AI-powered solution.

Company Size: Jerry.ai is a rapidly growing company, having reached profitability and backed by significant funding ($240M), indicating a phase of scaling operations and market penetration. This size suggests a balance between established processes and the agility of a startup.

Founded: Founded in 2017, Jerry.ai has a history of innovation and market development, evolving from its initial concept to a significant player with over 5 million customers and clear growth projections ($10B by 2030).

Team Structure:

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

• You will work directly with the CEO & Head of Product, Art Agrawal, indicating high visibility and direct impact on strategic decisions.

Methodology:

• Data-driven decision-making is central, with a team of analysts and data scientists supporting product development.

• AI and machine learning are core to the product's value proposition, influencing user experience and operational efficiency.

• A focus on building a "super app" for car ownership suggests a strategy of comprehensive service integration and end-to-end customer journey management.

• Emphasis on "craft and clarity" in design alongside functional AI capabilities.

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

📝 Enhancement Note: The company's rapid growth, profitability, and ambitious valuation target ($10B by 2030) suggest a high-performance culture. The emphasis on "craft and clarity" in design, coupled with AI integration, indicates a forward-thinking approach that values both user experience and technological innovation. The collaborative structure with a large engineering and product team highlights the importance of strong communication and cross-functional alignment for successful product launches.

📈 Career & Growth Analysis

Operations Career Level: This role is classified as "Staff," representing a senior individual contributor position. It signifies a high level of expertise, autonomy, and influence within the product and design organization. Staff designers are expected to lead complex projects, mentor junior team members, and significantly shape product strategy and design quality.

Reporting Structure: You will report directly to Kruise Sapstein, Head of Design, and will work closely with Art Agrawal, CEO & Head of Product. This direct line to leadership provides significant visibility and opportunity to influence strategic direction.

Operations Impact: The Staff Product Designer will have a direct and substantial impact on Jerry.ai's success by shaping the user experience of products used by millions. This impact extends to driving user acquisition, increasing engagement and retention, and reinforcing the brand's image as a trusted, effortless solution for car ownership. Design is explicitly positioned as the vehicle for bringing the company's vision to life.

Growth Opportunities:

• Design Leadership: Opportunity to influence design vision, mentor emerging designers, and contribute to building a world-class design culture at a rapidly scaling company.

• Strategic Product Influence: Direct involvement in shaping core product strategy and roadmap, with the potential to lead design for new product categories or major feature expansions.

• Skill Specialization: Deepen expertise in designing for AI-powered consumer applications, large-scale consumer marketplaces, and complex financial/insurance products.

• Career Advancement: Potential to move into Principal Designer or Design Lead roles as the company and design team continue to grow.

📝 Enhancement Note: The "Staff" title implies a role that is both highly technical and strategically influential. The direct reporting lines to the Head of Design and CEO underscore the importance of this position in driving business outcomes through design. The growth opportunities are framed around leadership, strategic impact, and specialization, aligning with typical career progression for senior designers in high-growth tech companies.

🌐 Work Environment

Office Type: While the role is designated as "TELECOMMUTE" and fully remote, Jerry.ai has physical office locations in Palo Alto, CA, Jersey City, NJ, and potentially other hubs. The company emphasizes collaboration, suggesting that even in a remote setting, there's an expectation of active engagement and communication.

Office Location(s): Palo Alto, California, United States is listed as a primary location, but the role is remote-eligible across the United States and Canada. Specific company office locations include Palo Alto, CA; Jersey City, NJ; Boston, MA; New York, NY; Raleigh, NC; Salt Lake City, UT; and Toronto, ON.

Workspace Context:

• Remote Collaboration: Expect a highly collaborative remote environment, utilizing digital tools for communication, design reviews, and brainstorming sessions.

• Tooling: Access to industry-standard design and collaboration tools will be provided to support effective remote work.

• Team Interaction: Regular interaction with Product Managers, Engineers, Data Scientists, and the Head of Design is expected, fostering a connected and integrated team experience despite geographical distribution.

Work Schedule: The standard work schedule is full-time (approximately 40 hours per week). However, given the remote nature and the fast-paced environment, flexibility is key. Expect some work outside of traditional hours to accommodate cross-functional team needs, project deadlines, and collaboration across different time zones.

📝 Enhancement Note: The explicit mention of remote work eligibility across the US and Canada, alongside physical office locations, highlights a flexible, distributed work model. The emphasis on collaboration in a remote setting suggests that strong communication skills and proactive engagement are critical for success. The work schedule flexibility is typical for senior roles in tech, balancing personal needs with business demands.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio by the design leadership. Focus on articulating your impact and ownership.

• Portfolio Presentation: A dedicated session to walk through your portfolio with the Head of Design and potentially other design/product leaders. Be prepared to discuss your process, decisions, and the measurable outcomes of your work.

• Cross-Functional Interviews: Meetings with Product Managers, Engineers, and Data Scientists to assess collaboration skills, technical understanding, and ability to integrate design into the broader product development lifecycle.

• Design Challenge/Whiteboarding Session: Potentially a design exercise to evaluate problem-solving skills, design thinking, and ability to articulate solutions under pressure.

• Final Round: Discussions with senior leadership (e.g., CEO) to assess cultural fit, strategic thinking, and alignment with Jerry.ai's vision.

Portfolio Review Tips:

• Quantify Impact: For each project, clearly state the problem, your specific role, the design solutions you implemented, and the resulting impact using metrics (e.g., % increase in conversion, % decrease in churn, user satisfaction scores).

• Showcase 0→1 Experience: Highlight projects where you led design from concept to launch, demonstrating your ability to navigate ambiguity and define new product areas.

• Design System Expertise: Feature examples of your involvement in building or evolving design systems, showing your understanding of scalability, consistency, and developer collaboration.

• Narrative Flow: Structure your case studies with a compelling story that guides the reviewer through your thought process and problem-solving approach.

• Tailor to Jerry.ai: Emphasize projects related to consumer apps, marketplaces, fintech, or insurance if available, and clearly articulate how your skills align with Jerry.ai's mission and challenges.

Challenge Preparation:

• Understand Jerry.ai's Business: Research Jerry.ai's products, target audience, market position, and competitive landscape.

• Focus on User-Centricity & Business Goals: Be prepared to balance user needs with business objectives, demonstrating how design can drive both.

• Articulate AI Integration: Think about how AI can enhance user experiences in car ownership and be ready to discuss potential design applications.

• Practice Communication: Rehearse explaining complex design decisions clearly and concisely, especially when discussing trade-offs and technical constraints.

📝 Enhancement Note: The interview process described is typical for senior design roles in tech, emphasizing portfolio strength, cross-functional collaboration, and strategic thinking. The advice for portfolio review and challenge preparation is tailored to highlight the specific needs of this role at Jerry.ai, such as demonstrating 0→1 experience, design system expertise, and quantifiable impact relevant to GTM success.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (highly probable, industry standard for collaborative design), Sketch, Adobe Creative Suite.

• Prototyping & Interaction: InVision, Framer, or Figma's prototyping capabilities.

• Design Systems: Tools and methodologies for component libraries, style guides, and design tokens.

• Collaboration: Slack, Zoom, Google Workspace (Docs, Sheets, Slides).

Analytics & Reporting:

• Product Analytics: Amplitude, Mixpanel, Google Analytics (for understanding user behavior, engagement, and conversion funnels).

• Data Visualization: Tableau, Looker, or internal dashboards for understanding performance metrics and communicating insights.

CRM & Automation:

• While not directly a designer's tool, understanding how design impacts CRM (e.g., lead generation forms, onboarding flows) and marketing automation is beneficial. Experience with tools like Salesforce or HubSpot from a user experience perspective could be a plus.

• AI/ML Integration: Familiarity with how AI/ML models are integrated into user-facing features and how design can facilitate their effective use.

📝 Enhancement Note: The expected tools align with current industry best practices for product design. Proficiency in Figma is almost a given for senior roles. Understanding analytics tools is crucial for a role focused on driving engagement and retention, as it allows designers to measure the impact of their work and iterate effectively, directly supporting GTM objectives. Familiarity with AI integration is a specific requirement for this role.

👥 Team Culture & Values

Operations Values:

• Craft & Clarity: A deep commitment to high-quality design execution, ensuring products are not only functional but also aesthetically pleasing and easy to understand.

• User-Centricity: Placing the user at the forefront of all design decisions, aiming to create effortless and delightful experiences for car owners.

• Data-Driven Innovation: Utilizing data and AI to inform design choices, identify opportunities, and optimize user journeys for maximum impact.

• Collaboration & Ego-lessness: Working effectively with cross-functional teams, valuing diverse perspectives, and prioritizing collective success over individual recognition.

• Speed & Agility: Embracing a fast-paced environment, iterating quickly, and delivering high-quality solutions efficiently.

Collaboration Style:

• Cross-Functional Integration: Close partnership with Product, Engineering, Research, and Data Science teams to ensure a holistic approach to product development.

• Feedback-Oriented: An open culture for giving and receiving constructive feedback to continuously improve design quality and product outcomes.

• Knowledge Sharing: Actively sharing insights, best practices, and learnings across the team and broader organization to foster collective growth and elevate design standards.

📝 Enhancement Note: The described values emphasize a blend of creative excellence, analytical rigor, and collaborative spirit. This is crucial for a role that bridges the gap between product vision and market execution, where design must align with data insights and business goals to drive GTM success. The emphasis on "speed and agility" is particularly relevant for a company aiming for rapid growth.

⚡ Challenges & Growth Opportunities

Challenges:

• Scaling Design Systems: Evolving and maintaining a robust design system across a rapidly expanding product suite and user base.

• Integrating AI Seamlessly: Designing intuitive and trustworthy AI-powered features that genuinely enhance the user experience without adding complexity.

• Balancing Craft with Speed: Delivering exceptional design quality while meeting aggressive product launch timelines in a fast-paced startup environment.

• Defining a New Category: Establishing Jerry.ai as the definitive "super app" for car ownership requires innovative design solutions that educate and guide users through a complex ecosystem.

Learning & Development Opportunities:

• Advanced AI Design: Gaining hands-on experience in designing for and with cutting-edge AI technologies.

• Strategic Product Leadership: Developing skills in influencing product roadmaps, mentoring teams, and shaping design strategy at a company-wide level.

• Industry Domain Expertise: Deepening knowledge in insurtech, fintech, and the automotive industry to create more impactful and contextually relevant designs.

• Cross-Functional Acumen: Enhancing understanding of engineering, product management, and data science workflows to foster even stronger collaboration.

📝 Enhancement Note: The challenges highlight the complexities of working in a fast-growing tech company with an innovative product. The growth opportunities are intentionally framed to leverage these challenges as learning experiences, focusing on specialized skills and leadership development relevant to the company's trajectory and the candidate's career progression.

💡 Interview Preparation

Strategy Questions:

• "How would you approach designing a new AI-powered feature for car insurance claims processing that prioritizes both speed and user trust?" (Focus on process, user empathy, AI considerations, and metrics.)

• "Describe a time you significantly influenced a product roadmap or strategy through your design work. What was your approach, and what was the outcome?" (Highlight strategic thinking, collaboration, and impact.)

Company & Culture Questions:

• "Based on your understanding of Jerry.ai, what do you see as the biggest design challenge or opportunity for the company in the next 1-2 years?" (Showcase research and strategic insight.)

• "How would you contribute to building and maintaining a high-craft design culture at Jerry.ai, especially in a remote setting?" (Focus on collaboration, mentorship, and advocacy.)

Portfolio Presentation Strategy:

• Start with the "Why": Clearly articulate the business problem and user need for each case study.

• Showcase Your Role & Process: Detail your specific contributions and the steps you took, from research and ideation to iteration and final execution. Use visuals effectively.

• Quantify Your Impact: Present concrete metrics and business outcomes (e.g., conversion rates, engagement uplift, retention improvements) to demonstrate the value of your design work.

• Highlight Design System Contribution: If applicable, show how you contributed to or leveraged design systems for efficiency and consistency.

• Tell a Story: Weave a narrative that engages the interviewer, demonstrating your passion, problem-solving skills, and strategic thinking. Be prepared to answer deep-dive questions about your decisions.

📝 Enhancement Note: These interview questions and preparation tips are designed to probe for the specific skills and mindset required for a Staff Product Designer at a company like Jerry.ai, emphasizing strategic thinking, quantifiable impact, and cross-functional collaboration. The focus on AI and design systems is crucial, as is the ability to articulate design's role in driving business metrics.

📌 Application Steps

To apply for this Staff Product Designer position:

• Submit your application through the provided link on Ashby.

• Curate Your Portfolio: Select 3-5 of your most impactful projects that best demonstrate your end-to-end product design capabilities, your experience with consumer products at scale, and your ability to drive measurable outcomes. Emphasize case studies that highlight your ownership and problem-solving process.

• Optimize Your Resume: Tailor your resume to highlight your 12+ years of experience, specific achievements in product design, experience with design systems, and any relevant industry experience (fintech, mobility, insurance). Use keywords from the job description.

• Prepare Your Narrative: Practice articulating your design philosophy, your approach to user research and problem-solving, and how your work has directly contributed to business goals and user growth. Be ready to discuss your portfolio in detail.

• Research Jerry.ai: Understand Jerry.ai's mission, products, target market, and recent company news. Prepare thoughtful questions about the company culture, the design team's vision, and the specific challenges of the role.

⚠️ 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.