Staff Product Designer

📍 Job Overview

Job Title: Staff Product Designer Company: Jerry.ai Location: United States Job Type: FULL_TIME Category: Product Design / User Experience Date Posted: December 15, 2025 Experience Level: Senior (12+ Years) Remote Status: Fully Remote

🚀 Role Summary

• Lead the design vision and execution for core product areas within Jerry's AI-powered car ownership platform, focusing on insurance, safety, and repairs.
• Drive the end-to-end design process for new, 0→1 features, transforming user insights from research and data into impactful and intuitive user experiences.
• Elevate the overall quality of UX and visual design by applying a strong craft and a focus on clarity, speed, and user delight across mobile and web platforms.
• Contribute to the strategic development and refinement of Jerry's design system, ensuring scalability, consistency, and visual excellence as the company grows.

📝 Enhancement Note: While the primary role is Product Design, the emphasis on AI, consumer products at scale, and driving measurable engagement and retention indicates a strong connection to Go-To-Market (GTM) and Revenue Operations principles. The successful candidate will need to understand how design directly impacts user acquisition, activation, and retention metrics, requiring collaboration with operations teams.

📈 Primary Responsibilities

• Spearhead the design strategy and execution for critical product initiatives, ensuring alignment with business objectives and user needs.
• Translate complex user problems into elegant, user-centered design solutions that simplify car ownership for millions of Americans.
• Collaborate closely with Product Managers, Engineers, and Data Scientists to define product roadmaps, identify user pain points, and iterate on designs based on performance data and user feedback.
• Develop and maintain comprehensive user flows, wireframes, prototypes, and high-fidelity mockups to effectively communicate design concepts and user journeys.
• Champion and evolve Jerry's design system, working with engineering to ensure its robust implementation and adoption across all product surfaces.
• Integrate AI capabilities thoughtfully into the user experience to enhance personalization, efficiency, and overall user satisfaction.
• Conduct user research, competitive analysis, and usability testing to inform design decisions and validate solutions.
• Mentor and guide junior designers, fostering a culture of high-quality design and continuous improvement.

📝 Enhancement Note: The responsibility to "apply AI to make our experience faster, clearer, and more personal" and to "drive measurable gains in engagement and retention" directly links this design role to revenue-generating activities. The candidate will need to demonstrate an understanding of how design impacts key operational metrics like conversion rates, customer lifetime value, and churn reduction.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong foundation in design principles, human-computer interaction, and visual arts is expected, often gained through formal education or equivalent practical experience.

Experience: Minimum of 12 years of professional product design experience, with a proven track record of shipping successful consumer-facing products at scale on both mobile and web platforms.

Required Skills:

• Exceptional Visual Design: A strong portfolio showcasing sophisticated visual aesthetics, attention to detail, and a keen eye for typography, color, and layout.
• Thoughtful UX Design: Demonstrated ability to create intuitive, user-centered experiences that solve complex problems and meet user needs effectively.
• End-to-End Project Ownership: Proven experience managing design projects from initial concept and user research through to final launch and post-launch iteration.
• Design Systems Expertise: Experience in building, maintaining, and scaling design systems in close collaboration with engineering teams.
• Consumer Product Focus: A portfolio rich with shipped consumer products, ideally demonstrating impact on user engagement and retention metrics.
• AI Integration: Understanding of how to leverage AI/ML to enhance user experiences and drive product innovation.
• Cross-functional Collaboration: Ability to work effectively with Product Managers, Engineers, Researchers, and Data Scientists.
• Communication & Storytelling: Excellent verbal and written communication skills, with the ability to articulate design decisions and influence stakeholders.
• Agile & Fast-Paced Environments: Adaptability and efficiency in delivering high-quality work within a dynamic startup setting.

Preferred Skills:

• Experience in marketplaces, fintech, mobility, or insurance industries.
• Familiarity with data analysis and using metrics to inform design decisions.
• Experience with user research methodologies and synthesis.

📝 Enhancement Note: The "12+ years" requirement for a Staff Product Designer role signals a need for deep strategic thinking, leadership potential, and a comprehensive understanding of product lifecycle management, not just execution. This level of experience typically implies involvement in product strategy and influencing GTM efforts through design.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Shipped Consumer Products at Scale: Showcase a minimum of 2-3 significant consumer-facing products or features that have been launched and are in active use by a large user base (millions).
• End-to-End Case Studies: Provide detailed case studies that walk through the entire design process, from problem identification and user research to ideation, prototyping, user testing, and final implementation. Clearly articulate your specific role and contributions.
• UX & Visual Design Excellence: Demonstrate a strong command of both user experience principles (information architecture, user flows, interaction design) and visual design execution (UI patterns, typography, color theory, visual hierarchy).
• Design System Contribution: Include examples of your work on design systems, such as creating new components, advocating for system adherence, or contributing to system documentation. Highlight how the system improved efficiency or consistency.
• Impact & Metrics: Quantify the impact of your design work whenever possible. Showcase how your designs contributed to key business objectives like increased user engagement, conversion rates, retention, or reduced friction in user journeys.

Process Documentation:

• Problem Definition & Research: Clearly outline the user problem or business opportunity you addressed, including the research methods used (e.g., user interviews, surveys, data analysis) and key insights derived.
• Design Exploration & Iteration: Detail your design process, including sketches, wireframes, interactive prototypes, and how you iterated based on feedback from user testing or cross-functional reviews.
• Collaboration & Alignment: Explain how you collaborated with product managers, engineers, and other stakeholders, demonstrating your ability to build consensus and align teams around a shared design vision.
• Systemic Thinking: Show how your designs integrate with or contribute to the broader product ecosystem and design system.

📝 Enhancement Note: For a Staff Designer role, the portfolio must go beyond simply showcasing screens. It needs to demonstrate strategic thinking, problem-solving capabilities, leadership in design initiatives, and a clear understanding of how design impacts business outcomes—aligning closely with the goals of Revenue Operations.

💵 Compensation & Benefits

Salary Range: $170,000 - $200,000 USD per year.

Benefits:

• Comprehensive Health Coverage: Includes health, dental, and vision insurance plans.
• Work-Life Balance: Generous paid time off (PTO) and paid parental leave.
• Retirement Planning: 401(K) plan with employer matching contributions.
• Wellness Support: Access to wellness benefits.
• Equity Opportunities: Potential for stock options or equity grants, aligning employee success with company growth.

Working Hours: Standard full-time employment, typically around 40 hours per week, with flexibility expected given the remote nature and the demands of a fast-paced startup environment.

📝 Enhancement Note: The listed salary range is competitive for a Staff Product Designer role in the US market, especially for a remote position with a well-funded, high-growth company like Jerry.ai. The inclusion of equity opportunities is standard for senior roles in startups and directly links compensation to company performance, a key concern for operations professionals.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, specifically focused on Automotive Services, Insurance Technology (Insurtech), Fintech, and AI-powered Consumer Applications. Jerry.ai operates in a massive, historically underserved market ($2T industry) ripe for disruption. Company Size: Jerry.ai has grown significantly, with over 5 million users and a team that includes 11 Product Managers, 55 Engineers, and 12 Analysts/Data Scientists, indicating a substantial, cross-functional organization. The company has reached profitability and is backed by substantial funding. Founded: Founded in 2017, Jerry.ai has a history of innovation and growth, evolving from its initial concept to a multi-faceted super app for car ownership.

Team Structure:

• Design Team: Led by Kruise Sapstein (Head of Design), the design team is positioned as crucial to the company's vision, aiming for high-craft and high-performance. This role will be a senior individual contributor within this team.
• Cross-functional Collaboration: Strong emphasis on partnership with Product Management, Engineering, and Data Science teams. The role requires close collaboration with 11 PMs, 55 engineers, and 12 analysts/data scientists.
• Leadership Involvement: Direct interaction with the CEO & Head of Product, Art Agrawal, highlighting the importance of design at the executive level.

Methodology:

• AI-Powered Innovation: Core to Jerry's approach is leveraging AI and Machine Learning to automate and simplify car ownership processes.
• Data-Driven Decisions: The presence of 12 analysts/data scientists suggests a strong reliance on data to identify opportunities, measure impact, and iterate on product features.
• User-Centric Design: The company emphasizes understanding customer needs and creating effortless experiences, with design being the primary vehicle for this vision.
• Agile Development: The fast-paced environment and emphasis on shipping quickly points to agile development methodologies.

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

📝 Enhancement Note: Jerry.ai's focus on disrupting a large, traditional industry with AI positions it as a high-growth tech company. The culture emphasizes innovation, data, and user experience, which means design is not just about aesthetics but about driving tangible business outcomes, aligning well with operations-focused roles.

📈 Career & Growth Analysis

Operations Career Level: This role is classified as a Staff Product Designer, representing a senior individual contributor level. It signifies a high degree of autonomy, strategic influence, and the expectation to lead significant design initiatives. Staff-level designers are expected to not only execute exceptionally but also to mentor others, define best practices, and shape the future direction of the product and design discipline within the company. In a GTM or RevOps context, this translates to influencing user acquisition funnels, retention strategies, and overall customer lifetime value through expert design.

Reporting Structure: The Staff Product Designer will report to the Head of Design, Kruise Sapstein. This direct line provides clear mentorship and strategic guidance while allowing for significant independent work. Collaboration will be extensive with Product Managers, Engineers, and Data Scientists, forming cross-functional project teams.

Operations Impact: The impact of this role is directly tied to customer acquisition, engagement, and retention. By designing "elegant, frictionless experiences that drive measurable gains in engagement and retention," the designer directly contributes to key operational metrics. Simplifying car ownership for millions of users translates to increased user base growth, higher customer lifetime value, and reduced churn, all critical KPIs for Revenue and Sales Operations. The application of AI in design also aims to streamline processes, reducing friction and improving operational efficiency from a user perspective.

Growth Opportunities:

• Leadership in Design: Opportunity to shape the design culture and standards at Jerry.ai, potentially growing into a Design Lead or Principal Designer role as the company scales.
• Strategic Influence: Contribute to product strategy and roadmap development, influencing the direction of a rapidly growing company in a massive market.
• Skill Expansion: Deepen expertise in AI-driven product design, consumer marketplaces, and insurtech/fintech sectors.
• Mentorship and Team Building: Opportunity to mentor junior designers and contribute to building a world-class design team.
• Impactful Product Development: Work on features that directly impact millions of users and contribute to the company's goal of becoming a $10B company.

📝 Enhancement Note: The Staff level designation implies that this role is not just about execution but about strategic contribution. The candidate is expected to influence product strategy and operations by making design decisions that demonstrably improve key business metrics like conversion, retention, and customer lifetime value.

🌐 Work Environment

Office Type: This is a fully remote position within the USA, offering significant flexibility and autonomy. The company culture is built around collaboration and high performance, irrespective of physical location.

Office Location(s): While the role is remote, the company's primary operations and headquarters are implied to be in the USA, with a focus on serving the American market. The company has a significant engineering and data science presence, suggesting a robust digital infrastructure.

Workspace Context:

• Collaborative Digital Environment: Expect to work in a highly collaborative digital space, utilizing tools for communication, project management, and design co-creation. The emphasis is on asynchronous and synchronous communication to foster teamwork.
• Operations Tools & Technology: Access to industry-standard design software (e.g., Figma, Sketch), prototyping tools, and collaboration platforms. The design team works closely with engineering and data science, implying access to relevant project management and analytics tools.
• Team Interaction: Regular interaction with a distributed team of Product Managers, Engineers, Data Scientists, and fellow Designers. Opportunities for virtual team-building and knowledge-sharing sessions will be prevalent.

Work Schedule: While the core expectation is a full-time role (approximately 40 hours per week), the remote nature allows for a degree of flexibility in structuring the workday. However, the fast-paced environment and need for cross-functional collaboration mean responsiveness and timely delivery are critical. This flexibility is beneficial for accommodating deep work sessions necessary for complex design tasks and data analysis.

📝 Enhancement Note: The fully remote aspect of this role requires strong self-discipline and communication skills. The company's focus on data and collaboration suggests a digital-first approach to its work environment, where successful operations and design hinge on effective remote teamwork and tool utilization.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Application & Portfolio Review: Submit your resume and a link to your design portfolio. The hiring team will assess your experience, skills, and the quality/impact of your past work.
• Screening Call: A brief conversation with a recruiter or hiring manager to discuss your background, motivations, and alignment with the role and company culture.
• Design Exercise/Case Study: You may be asked to complete a take-home design challenge or present a deep dive into a past project from your portfolio. This will assess your problem-solving approach, design process, and ability to articulate your work.
• Interviews with Cross-Functional Teams: Interviews with Product Managers, Engineers, Data Scientists, and potentially other Designers to evaluate your collaboration skills, technical understanding, and ability to integrate into the existing team structure.
• Interview with Head of Design: A final discussion with Kruise Sapstein to assess strategic thinking, leadership potential, and cultural fit.

Portfolio Review Tips:

• Focus on Impact: Prioritize case studies that clearly demonstrate the business impact and user value of your designs. Quantify results using metrics (e.g., conversion lift, engagement increase, retention improvement) wherever possible.
• Showcase Your Process: Clearly articulate your role in each project, your design process (research, ideation, iteration, testing), and the rationale behind your decisions.
• Highlight End-to-End Ownership: Demonstrate your ability to take a project from conception through to launch and iteration, showcasing your versatility across the entire product lifecycle.
• Design Systems and Scale: Include examples of your experience with design systems and how you've applied them to ensure consistency and scalability for large user bases.
• Clarity and Storytelling: Present your work clearly and concisely, using compelling narratives to explain the problem, your solution, and the outcome. Tailor the presentation to highlight aspects most relevant to Jerry.ai's mission and the Staff Designer role.

Challenge Preparation:

• Understand the Business: Research Jerry.ai's mission, target audience, product offerings, and competitive landscape. Understand the core problems they are solving in car ownership.
• Design for AI: Be prepared to discuss how you would leverage AI to enhance user experiences in the context of car ownership (e.g., personalized recommendations, proactive assistance, streamlined processes).
• Focus on Metrics: Think about how you would measure the success of your design solutions. What KPIs would you track? How would you tie design decisions to measurable business outcomes?
• Communication is Key: Practice articulating your thought process, design choices, and potential trade-offs clearly and confidently. Be ready to answer questions about your approach and decision-making.

📝 Enhancement Note: The emphasis on a portfolio showcasing "shipped consumer products at scale" and "measurable gains in engagement and retention" strongly suggests that the company views design as a critical driver of business outcomes, akin to how operations professionals view their metrics. Candidates must be prepared to demonstrate this link.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (highly probable given industry trends), Sketch, Adobe Creative Suite.
• Collaboration Platforms: Slack, Jira, Confluence, Asana, or similar project management and communication tools.
• Design System Management: Tools for component libraries, documentation, and version control (often integrated within Figma or standalone platforms).

Analytics & Reporting:

• Product Analytics: Amplitude, Mixpanel, Google Analytics, or similar platforms for tracking user behavior, engagement, and conversion funnels.
• Data Visualization: Tableau, Looker, or internal dashboards for understanding user data and performance metrics.
• A/B Testing Tools: Optimizely, VWO, or similar platforms for experimental design and validation.

CRM & Automation:

• While not directly a design tool, understanding CRM (e.g., Salesforce, HubSpot) and marketing automation principles can be beneficial for context on user lifecycle management and customer segmentation.

📝 Enhancement Note: The role requires proficiency in modern design tools and a strong understanding of how design integrates with analytics and product management workflows. Familiarity with data analysis tools is crucial for demonstrating the impact of design decisions, a common requirement for operations-minded professionals.

👥 Team Culture & Values

Operations Values:

• User-Centricity & Empathy: A deep commitment to understanding and serving the needs of car owners, making complex processes effortless and affordable. This translates to operational efficiency for the user.
• Innovation & AI-Driven Solutions: A drive to leverage cutting-edge technology, particularly AI, to disrupt traditional industries and create novel solutions. This mirrors the operational drive for efficiency through automation.
• Craftsmanship & Quality: A high standard for the quality of work, from code to design, ensuring a polished and reliable user experience. This aligns with operations’ focus on process integrity and output quality.
• Speed & Agility: The ability to move quickly, iterate, and adapt in a fast-paced startup environment. This is critical for operations to respond to market changes and customer needs.
• Collaboration & Egolessness: A culture where individuals work together effectively, prioritize team success over individual accolades, and are open to feedback and diverse perspectives.

Collaboration Style:

• Cross-Functional Partnership: Strong emphasis on close collaboration between Design, Product, Engineering, and Data Science. This integrated approach ensures that design decisions are informed by technical feasibility, business goals, and user data.
• Data-Informed Design: Decisions are expected to be backed by data and user research, fostering a culture of evidence-based problem-solving.
• Open Communication: Encouragement of direct and honest communication, with a focus on constructive feedback to drive continuous improvement.
• Shared Ownership: A sense of collective responsibility for the product's success, where team members contribute to problem-solving regardless of their specific discipline.

📝 Enhancement Note: The company's values of user-centricity, innovation, speed, and collaboration are directly transferable to operational excellence. A candidate who embodies these values will likely excel in an environment that values data-driven decisions and efficient problem-solving, common traits in successful operations professionals.

⚡ Challenges & Growth Opportunities

Challenges:

• Scaling Design for Millions: Ensuring design quality and consistency as the user base grows exponentially while maintaining a delightful and intuitive experience.
• Simplifying Complex Domains: Translating complicated areas like insurance, financing, and car maintenance into easily understandable and manageable user flows.
• Integrating AI Seamlessly: Leveraging AI capabilities effectively without making the user experience overly complex or opaque.
• Fast-Paced Environment: Adapting to rapid product iterations and evolving business priorities, requiring efficient design workflows and decision-making.
• Balancing Craft and Speed: Delivering high-quality, polished design work quickly to meet aggressive product timelines.

Learning & Development Opportunities:

• Deep Dive into Insurtech/Fintech: Gain specialized knowledge in the insurance and financial technology sectors, understanding their unique challenges and opportunities.
• AI-Powered Product Design: Become an expert in designing for AI-enhanced consumer products, shaping the future of user interaction with intelligent systems.
• Leadership & Mentorship: Develop leadership skills by mentoring junior designers and influencing design strategy at a senior level.
• Cross-Functional Expertise: Enhance understanding of product management, data science, and engineering processes through close collaboration.
• Strategic Impact: Contribute significantly to the growth and success of a rapidly scaling company, potentially impacting its trajectory toward a $10B valuation.

📝 Enhancement Note: The challenges presented are common in high-growth tech companies and require not only strong design skills but also strategic thinking, resilience, and a proactive approach to problem-solving – traits highly valued in operations roles.

💡 Interview Preparation

Strategy Questions:

• "How would you approach designing a new feature for Jerry that leverages AI to proactively alert users about upcoming maintenance needs?"
  • Preparation Advice: Focus on user needs (avoiding surprises, cost savings), AI capabilities (predictive analytics, data integration), and user experience (clear notifications, actionable insights). Discuss data sources, potential user confusion, and how to ensure trust.
• "Describe a time you owned a significant product design initiative from 0→1. What were the key challenges, how did you overcome them, and what was the measurable outcome?"
  • Preparation Advice: Select a strong case study from your portfolio. Clearly articulate the problem, your role, your process (research, ideation, iteration), how you collaborated with stakeholders, and the quantifiable impact on users or business metrics.
• "How would you design an experience to increase user retention for Jerry's insurance product?"
  • Preparation Advice: Think about common retention drivers: value proposition, ease of use, personalized support, rewards, community. Discuss how design can enhance these aspects. Consider data points you'd analyze to identify drop-off points.

Company & Culture Questions:

• "What excites you about Jerry's mission to simplify car ownership, and how do you see design playing a role in that?"
  • Preparation Advice: Research Jerry's "super app" concept and their target audience. Connect their mission to your passion for user-centered design and problem-solving.
• "How do you ensure your design work aligns with business objectives and contributes to measurable outcomes like engagement and retention?"
  • Preparation Advice: Discuss your experience working with metrics, collaborating with data teams, and using data to inform design decisions. Highlight instances where your design directly impacted KPIs.
• "Describe your experience working in a fast-paced, remote, and collaborative environment."
  • Preparation Advice: Emphasize your communication skills, self-discipline, proactive approach to collaboration, and comfort with agile methodologies.

Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly outline: The Problem, Your Role, The Process, The Solution, and The Outcome (with metrics).
• Highlight Strategic Thinking: Explain why you made certain design decisions, not just what you designed. Discuss trade-offs and how you balanced user needs with business goals.
• Showcase Design Systems Work: If applicable, detail your contribution to design systems and how they enabled efficiency, consistency, and scalability.
• Demonstrate Collaboration: Mention how you worked with PMs, engineers, and other stakeholders, and how you incorporated their feedback.
• Be Prepared for Questions: Anticipate questions about your process, decisions, challenges, and the impact of your work.

📝 Enhancement Note: The interview preparation advice emphasizes demonstrating a data-driven mindset and an understanding of business impact, aligning with the expectations for operations professionals. Candidates should be ready to speak the language of metrics, ROI, and strategic contribution.

📌 Application Steps

To apply for this Staff Product Designer position:

• Submit your application through the provided link on Ashby.
• Portfolio Customization: Ensure your portfolio prominently features case studies that demonstrate end-to-end ownership of consumer products, quantifiable impact (engagement, retention), and experience with design systems. Tailor your presentation to highlight how your skills align with Jerry.ai's mission and the challenges of scaling AI-driven consumer products.
• Resume Optimization: Update your resume to emphasize your 12+ years of experience, your leadership in design initiatives, your contributions to shipped products at scale, and any relevant experience in marketplaces, fintech, or insurance. Use keywords from the job description.
• Interview Preparation: Thoroughly review the "Interview Preparation" section above. Practice articulating your design process, strategic thinking, and ability to drive business outcomes through design. Prepare specific examples for behavioral and situational questions.
• Company Research: Deeply understand Jerry.ai's business model, product suite, target audience, and company culture. Be ready to articulate why you are a strong fit for their specific goals and values, particularly their AI-first approach and mission to simplify car ownership.

⚠️ 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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