Sr. Product Designer

📍 Job Overview

Job Title: Sr. Product Designer

Company: Jerry.ai

Location: United States

Job Type: FULL_TIME

Category: Product Design / User Experience

Date Posted: 2025-11-10

Experience Level: 5-10 Years

Remote Status: Fully Remote (USA)

🚀 Role Summary

• Drive the end-to-end product design lifecycle for Jerry.ai’s AI-powered car ownership platform, focusing on user experience and intuitive interface design.

• Translate complex, data-heavy problems and requirements into simple, elegant, and user-friendly workflows across mobile and web platforms.

• Collaborate closely with Product Management, Engineering, and Data Science teams to conceptualize, design, and iterate on features that enhance user decision-making for insurance, safety, and repairs.

• Contribute to the evolution of Jerry.ai's design system, ensuring consistency, scalability, and a high standard of visual and interactive design across all products.

📝 Enhancement Note: This role is critical for the "form" of Jerry.ai's product, complementing its existing "functionality." The emphasis on AI integration suggests a need for designers who can leverage AI to personalize and automate user experiences, a key differentiator for the company.

📈 Primary Responsibilities

• Partner with Product Managers and Engineers to deeply understand user problems, define feature scope, and design solutions that achieve measurable business and user outcomes.

• Develop comprehensive design artifacts, including user flows, low-fidelity wireframes, high-fidelity mockups, and interactive prototypes to effectively communicate design concepts and solutions.

• Lead UX explorations for complex product challenges, focusing on structuring intuitive workflows that simplify the multifaceted aspects of car ownership and management.

• Utilize user research methodologies, quantitative analytics, and A/B testing results to inform design decisions, validate design approaches, and drive continuous improvement.

• Collaborate with a team of designers to maintain and evolve the company's design system, ensuring brand consistency and efficient design implementation across platforms.

• Thoughtfully integrate AI capabilities into the user experience to enhance clarity, deliver personalized insights, and enable seamless automation of car-related tasks.

📝 Enhancement Note: The responsibilities highlight a strong emphasis on data-informed design and iterative development, common in fast-paced tech environments. The need to "simplify data-heavy experiences" points to a significant challenge in translating complex insurance and automotive data into accessible user interfaces.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong understanding of design principles, user-centered design methodologies, and visual communication is expected, often gained through formal education in Design, HCI, or related fields, or through extensive professional experience.

Experience: 5+ years of dedicated experience in product design, with a significant focus on consumer-facing mobile or web applications, either from in-house roles or agency work.

Required Skills:

• A robust portfolio demonstrating strong UX thinking, data-informed decision-making, and the creation of clean, intuitive interface designs.

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

• Demonstrated comfort and effectiveness collaborating with Product Managers and Engineers to define scope, prioritize solutions, and execute rapid iterations.

• Proficiency in Figma for design and rapid prototyping, with the ability to clearly communicate design ideas and interactions.

• Solid understanding of design systems, including experience in using and evolving them to ensure consistency and facilitate scalable design solutions.

Preferred Skills:

• Experience within marketplaces, fintech, insurance, or mobility sectors.

• Familiarity with user research methodologies and the ability to leverage insights to drive design decisions.

• Experience with AI-driven product features and understanding of their design implications.

• Knowledge of accessibility best practices in UI/UX design.

📝 Enhancement Note: The "5+ years of experience" is a guideline, with the portfolio and demonstrated capabilities being the primary evaluation criteria. The preference for marketplace, fintech, or insurance experience suggests a desire for candidates who can quickly grasp the nuances of Jerry.ai's industry.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A curated portfolio showcasing a minimum of 3-5 diverse projects that highlight your end-to-end design process, from problem definition to final UI.

• Demonstrate a clear understanding of user-centered design principles and how you applied them to solve specific user problems.

• Include case studies that detail your approach to translating complex data or requirements into intuitive user flows and interfaces.

• Showcase your ability to work with or contribute to design systems, emphasizing consistency and scalability in your designs.

Process Documentation:

• For each project in your portfolio, clearly articulate the problem statement, your role, the design process followed, key decisions made, and the final outcome or impact.

• Illustrate how you leveraged user research, data analytics, or A/B testing to inform your design choices and measure success.

• Provide examples of your collaboration with cross-functional teams (PMs, Engineers) throughout the design lifecycle.

• Showcase your proficiency in Figma and other relevant design and prototyping tools within your case studies.

📝 Enhancement Note: The portfolio is paramount for this role, serving as the primary evidence of a candidate's design thinking, problem-solving skills, and ability to execute. Expect to present detailed case studies that walk interviewers through your strategic process and design rationale.

💵 Compensation & Benefits

Salary Range: The provided salary range for this role is $130,000 - $160,000 USD per year. This range is based on market conditions for a Sr. Product Designer role in the United States, considering the company's funding and growth trajectory, and the experience level required.

Benefits:

• Comprehensive health, dental, and vision coverage.

• Generous paid time off (PTO) policy.

• Paid parental leave.

• 401(K) plan with employer matching contributions.

• Wellness benefits to support employee well-being.

• Opportunities for equity grants as part of the total compensation package.

Working Hours: The standard working hours are approximately 40 hours per week, aligning with full-time employment expectations. Given the remote nature, flexibility in scheduling may be available, but core collaboration hours will need to be observed.

📝 Enhancement Note: The salary range is competitive for a Sr. Product Designer in the US market, especially for a remote role at a well-funded startup. The inclusion of equity opportunities signifies potential for significant upside beyond base salary, aligning with the company's ambitious growth targets.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, specifically focused on Automotive Services, Insurance Technology (Insurtech), and Fintech. Jerry.ai operates within the multi-trillion dollar car ownership industry, aiming to disrupt traditional analog processes with an AI-powered digital solution.

Company Size: Jerry.ai has grown significantly, with the product organization alone comprising 11 PMs, 55 Engineers, and 12 Analysts/Data Scientists. The overall company size is not explicitly stated but is implied to be substantial given its funding and employee count in key departments.

Founded: Jerry.ai was founded in 2017. The company has achieved profitability and is backed by $240 million in funding, with a stated goal of becoming a $10 billion company by 2030. This indicates a growth-oriented, ambitious, and innovative culture.

Team Structure:

• The design team is led by Kruise Sapstein, Head of Design, who is focused on building a high-performing, high-craft design culture. The Sr. Product Designer will not be a "cog in a big design machine" but a key collaborator within a focused and impactful design function.

• Collaboration is structured to be direct, with the designer working closely with Product Managers (including CEO & Head of Product Art Agrawal), engineers, and data scientists.

Methodology:

• Jerry.ai emphasizes a data-driven approach, leveraging analytics and experimentation to inform design decisions and measure outcomes.

• Workflow planning and optimization are central to the product's mission of simplifying car ownership.

• Automation, particularly through AI, is a core component of their strategy to enhance user experience and efficiency.

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

📝 Enhancement Note: Jerry.ai is positioned as a disruptor in a massive, underserved market. The culture is likely fast-paced, innovative, and focused on tangible results, driven by strong leadership and significant investment. The emphasis on "curious and egoless people" suggests a collaborative and growth-minded environment.

📈 Career & Growth Analysis

Operations Career Level: This role is defined as a Senior Product Designer. In the context of operations and product development, this signifies a level of individual contributor expertise requiring significant autonomy, strategic thinking, and the ability to mentor or guide less experienced designers. Senior designers are expected to lead complex projects, influence product strategy, and contribute to the overall design vision and standards of the organization.

Reporting Structure: The Sr. Product Designer will report directly to Kruise Sapstein, Head of Design. This direct line of reporting offers visibility to design leadership and opportunities for direct mentorship and strategic input. The role also requires close collaboration with Art Agrawal, CEO & Head of Product, indicating a flat organizational structure where design has direct influence on key product decisions.

Operations Impact: The impact of this role is substantial. By designing intuitive and efficient user experiences for car ownership, the Sr. Product Designer directly influences customer acquisition, retention, satisfaction, and the overall adoption of Jerry.ai's services (insurance, maintenance, safety, financing). A well-designed product can lead to increased user engagement, conversion rates, and ultimately, contribute significantly to the company's revenue goals and market expansion.

Growth Opportunities:

• Design Leadership: As Jerry.ai scales, there will be opportunities to grow into lead design roles, manage design projects, or even build and lead specialized design teams.

• Skill Specialization: Deepen expertise in areas such as AI-driven design, complex data visualization, or specific product domains like insurtech or fintech.

• Product Strategy Influence: Contribute more significantly to product strategy and roadmap planning, leveraging design insights to identify new opportunities and threats.

• Mentorship: Mentor junior designers, contributing to the development of the broader design team's capabilities and craft.

📝 Enhancement Note: The "Sr." designation implies expectations of leadership in design thinking and execution, not necessarily people management. The direct access to CEO and Head of Design is a significant growth indicator, suggesting high impact potential.

🌐 Work Environment

Office Type: This is a Fully Remote position, allowing employees to work from anywhere within the United States. This offers maximum flexibility and autonomy.

Office Location(s): While the company is based in the US, the role is remote, meaning there is no specific office location requirement for the employee. Jerry.ai operates with a distributed team model.

Workspace Context:

• The remote work environment necessitates strong self-discipline, proactive communication, and effective use of digital collaboration tools.

• The company provides access to essential design tools and technologies (like Figma) to facilitate remote work and design execution.

• Opportunities for team interaction will primarily be through virtual meetings, Slack, and other digital communication platforms, fostering a culture of asynchronous and synchronous collaboration.

Work Schedule: The role is full-time (approximately 40 hours per week). While remote, maintaining consistent availability for team meetings, design critiques, and cross-functional collaboration during core business hours (likely aligned with US time zones) is expected. Flexibility may be offered in how the 40 hours are structured, but responsiveness is key.

📝 Enhancement Note: The fully remote nature is a significant perk, appealing to candidates who value flexibility. However, it also requires strong communication and organizational skills to thrive in a distributed team environment. Expect a high reliance on digital collaboration tools.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Application & Portfolio Review: Submit your resume and a compelling portfolio. The hiring team will assess your experience, UX thinking, visual design skills, and overall fit for the role.

• Screening Call: A brief call with a recruiter or hiring manager to discuss your background, motivations, and initial fit.

• Design Challenge/Case Study Presentation: You will likely be given a design challenge or asked to present a case study from your portfolio. This is where you'll demonstrate your problem-solving process, design rationale, and ability to articulate complex ideas clearly. Focus on showing how you think and why you made certain design decisions, especially in translating complex data into simple solutions.

• Team Interviews: Interviews with the Head of Design, Product Managers, Engineers, and potentially other designers. These sessions will assess your collaboration skills, technical proficiency, understanding of product strategy, and cultural fit. Expect questions about your experience with data-informed design and AI.

• Final Interview: Potentially with the CEO & Head of Product, Art Agrawal, to discuss your vision, strategic thinking, and alignment with the company's mission and growth objectives.

Portfolio Review Tips:

• Curate Selectively: Choose 3-5 of your strongest projects that best represent the skills required for this Sr. Product Designer role (UX thinking, data-informed design, complex problem-solving, clean UI).

• Tell a Story: For each project, clearly articulate the problem, your specific role and contributions, your design process, the challenges you faced, the decisions you made (and why), and the measurable outcomes or impact. Use visuals effectively to guide the narrative.

• Show Your Process: Don't just show final screens. Include sketches, wireframes, user flows, prototypes, and evidence of user testing or data analysis. This demonstrates your thinking from start to finish.

• Highlight Data & AI: If you have projects involving complex data or AI integration, explicitly call these out, explaining how you approached designing for these areas.

• Tailor to Jerry.ai: Research Jerry.ai's products and mission. If possible, subtly tailor your presentation to show how your skills align with their specific challenges in simplifying car ownership.

Challenge Preparation:

• Practice Articulating Your Process: Be ready to walk through your design process for a given problem, explaining your rationale at each step.

• Focus on "Why": For every design decision, be prepared to explain the "why" behind it, linking it back to user needs, business goals, or data insights.

• Consider Trade-offs: Be ready to discuss design trade-offs and how you prioritize solutions when faced with constraints (technical, time, etc.).

• Prepare Questions: Have thoughtful questions ready for the interviewers about their design process, challenges, culture, and vision for the product.

📝 Enhancement Note: The interview process is designed to thoroughly assess not only design craft but also strategic thinking, collaboration abilities, and problem-solving skills relevant to Jerry.ai's unique market and AI-driven approach. A strong portfolio presentation is crucial.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: This is explicitly mentioned as a required skill and will be the primary tool for UI design, prototyping, and collaboration. Proficiency in its advanced features for component management, auto layout, and interactive prototyping is expected.

• Prototyping Tools: Beyond Figma, experience with other rapid prototyping tools that facilitate quick iteration and user testing is valuable.

Analytics & Reporting:

• Experience leveraging data from analytics platforms (e.g., Amplitude, Mixpanel, Google Analytics) to inform design decisions. The ability to interpret user behavior data, conversion funnels, and A/B test results is crucial.

CRM & Automation:

• While not directly a CRM role, understanding how user data from CRM-like systems and user behavior analytics informs the design of features that drive engagement and loyalty is important.

• Understanding of how AI and automation are integrated into user experiences to streamline processes.

📝 Enhancement Note: The emphasis on Figma and data-informed design highlights a modern, agile product development environment. Candidates should be comfortable working with data to justify design choices and understand how their designs contribute to broader business objectives.

👥 Team Culture & Values

Operations Values:

• High Craft & Excellence: A strong emphasis on quality in design, aiming to elevate the user experience and brand perception.

• Data-Driven Decision Making: Design choices are expected to be informed by user research, analytics, and experimentation, promoting a culture of evidence-based design.

• Collaboration & Ego-lessness: Working effectively with cross-functional teams (PMs, Engineers, Data Scientists) with a focus on shared goals rather than individual credit.

• Innovation & AI Integration: A forward-thinking approach to leveraging technology, particularly AI, to solve user problems and create unique product value.

• User-Centricity: A commitment to understanding and serving the needs of millions of car owners, simplifying a complex and often frustrating aspect of life.

Collaboration Style:

• Cross-functional Partnership: The design team works in close collaboration with Product Management and Engineering from ideation through to launch and iteration.

• Design Critiques: An expectation of regular design reviews and feedback sessions to ensure high standards and shared understanding.

• Knowledge Sharing: A culture that encourages sharing best practices, learning from each other, and collectively improving the design output.

📝 Enhancement Note: The culture seems to value both high-quality execution and collaborative problem-solving. The "egoless" aspect suggests a team that prioritizes the product's success and open feedback over individual ego.

⚡ Challenges & Growth Opportunities

Challenges:

• Simplifying Complexity: Translating the intricate world of car insurance, maintenance, financing, and repairs into intuitive, user-friendly digital experiences is a significant ongoing challenge.

• Data Heavy Environments: Designing effective interfaces for data-rich applications requires a strategic approach to information architecture, visualization, and user guidance.

• AI Integration: Thoughtfully applying AI to enhance user experience without creating confusion or over-promising requires careful design and iteration.

• Scaling Design Systems: As the product suite grows, maintaining and evolving a robust design system to ensure consistency and efficiency across all touchpoints will be critical.

• Remote Collaboration: Thriving in a fully remote environment requires strong communication, self-management, and proactive engagement.

Learning & Development Opportunities:

• Deep Dive into AI in Design: Gain hands-on experience applying AI to enhance user experiences in a real-world consumer product.

• Industry Expertise: Develop specialized knowledge in insurtech, fintech, and the automotive services market.

• Product Strategy Contribution: Grow from executing design tasks to influencing product strategy and roadmap based on design insights.

• Mentorship & Leadership: Opportunity to mentor junior designers and contribute to the growth of the design team's capabilities.

• Exposure to Fast-Paced Growth: Experience working in a rapidly scaling startup environment with significant funding and ambitious goals.

📝 Enhancement Note: The challenges presented are core to Jerry.ai's mission and offer significant opportunities for skill development and impact. The role is ideal for a designer who enjoys tackling complex problems and wants to be at the forefront of AI-driven product innovation.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to design for a highly complex or data-intensive product. How did you simplify it for the user?" (Focus on your process, user research, and iterative approach).

• "How do you approach integrating AI into a user experience? What are the potential pitfalls, and how do you mitigate them?" (Demonstrate understanding of AI ethics, transparency, and user trust).

• "Walk us through a project from your portfolio where you had to collaborate closely with PMs and engineers to define scope and deliver a solution. What was your role, and what were the key outcomes?" (Highlight your collaboration skills and ability to influence product decisions).

• "How do you leverage data and analytics to inform your design decisions? Can you provide an example?" (Showcase your data-informed design methodology).

Company & Culture Questions:

• "What excites you about Jerry.ai's mission to simplify car ownership?" (Show genuine interest and alignment with the company's purpose).

• "How do you contribute to a high-craft design culture, especially in a remote environment?" (Discuss your approach to design quality, collaboration, and feedback).

• "Describe your experience working with design systems. How do you ensure consistency and scalability?" (Highlight your understanding of design system best practices).

Portfolio Presentation Strategy:

• Structure: For each case study, follow a clear narrative: Problem -> Your Role -> Process -> Solution -> Outcome/Impact.

• Visuals: Use high-quality visuals (wireframes, mockups, prototypes) to illustrate your points. Avoid walls of text.

• Focus on "Why": Constantly explain the reasoning behind your design decisions. Why this flow? Why this UI element? Why this solution? Connect decisions back to user needs and business goals.

• Quantify Impact: Whenever possible, use metrics to demonstrate the success of your designs. If exact numbers aren't available, discuss the intended impact and how it would be measured.

• Be Prepared for Questions: Anticipate questions about your process, trade-offs, and alternative solutions. Be open to constructive feedback.

📝 Enhancement Note: The interview process will likely test your ability to think strategically, collaborate effectively, and articulate your design process with clarity and conviction. Be ready to showcase your best work and explain the "why" behind every decision.

📌 Application Steps

To apply for this Sr. Product Designer position:

• Submit your application through the provided link on Ashby.

• Portfolio Customization: Ensure your portfolio is up-to-date and highlights projects that demonstrate your expertise in UX thinking, data-informed design, and translating complex problems into intuitive interfaces, preferably with examples of mobile or web consumer products.

• Resume Optimization: Tailor your resume to emphasize your 5+ years of relevant experience, proficiency in Figma, and any experience with AI, marketplaces, fintech, or insurance. Use keywords from the job description.

• Portfolio Walkthrough Practice: Prepare to present 1-2 key projects from your portfolio in detail, focusing on your process, decision-making, and impact. Practice articulating your "why" clearly and concisely.

• Company Research: Thoroughly research Jerry.ai, its products, mission, and recent news to understand their business model, user base, and market position. Prepare questions that demonstrate your engagement and strategic thinking about their product challenges.

⚠️ 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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