Lead Product Designer at Jerry.ai

📍 Job Overview

Job Title: Lead Product Designer Company: Jerry.ai Location: San Francisco, California, United States Job Type: FULL_TIME Category: Product Design / User Experience (UX) Date Posted: August 11, 2025 Experience Level: 5-10 years

🚀 Role Summary

Drive the end-to-end design process for new features and product evolution within a rapidly growing, pre-IPO startup environment, focusing on user-centric design principles.
Collaborate closely with Product Managers and fellow Designers to translate complex user needs and business objectives into intuitive, visually appealing, and highly usable mobile and web experiences.
Own the creation of design assets, including user flows, wireframes, interactive prototypes, and detailed specifications, ensuring brand consistency and adherence to platform-specific design patterns.
Leverage user feedback, A/B testing insights, and market advancements to continuously iterate and refine product designs, directly impacting millions of users.
Contribute to strategic product discovery through structured workshops and conceptualization, shaping the direction of Jerry.ai's car ownership super app.

📝 Enhancement Note: While the job title is "Lead Product Designer," the description emphasizes a hands-on, individual contributor role within a small team, with responsibility for end-to-end delivery and significant impact on product direction. This suggests the "Lead" aspect may refer to leadership in design execution and strategic thinking rather than extensive team management, at least initially, given the team size aiming to double.

📈 Primary Responsibilities

Lead the design and execution of new features and product enhancements, from initial concept and user research through to final implementation and post-launch analysis.
Develop comprehensive UX deliverables, including user personas, journey maps, site maps, wireframes, interactive prototypes, and detailed design specifications.
Champion user-centric design methodologies, conducting user research, usability testing, and leveraging A/B testing results to inform design decisions and optimize user experience.
Ensure brand consistency and visual integrity across all Jerry.ai platforms, creating and maintaining a robust design system and style guides.
Facilitate product discovery workshops, brainstorming sessions, and design critiques to foster innovation and align design solutions with product strategy and business goals.
Manage multiple design projects concurrently, ensuring timely delivery of high-quality design assets within an agile development environment.
Stay abreast of emerging design trends, mobile application patterns (iOS Human Interface Guidelines, Android Material Design), and competitive landscape to drive product innovation.

📝 Enhancement Note: The responsibilities highlight a strong blend of strategic product thinking and hands-on design execution. Emphasis on "end-to-end delivery," "managing design projects throughout the product life cycle," and "guiding product direction" indicates a senior-level individual contributor expected to own significant aspects of the product's user experience.

🎓 Skills & Qualifications

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

Experience: 5-10 years of proven experience in product design, UX/UI design, or interaction design, with a strong portfolio showcasing consumer-facing mobile or web applications.

Required Skills:

Demonstrated expertise in user-centered design processes and methodologies.
Proficiency in creating compelling screen flows, rapid prototypes, layout patterns, and information architecture.
Advanced proficiency with design and prototyping tools, with a specific emphasis on Figma.
Strong understanding of platform-specific design patterns, including iOS Human Interface Guidelines and Android Material Design.
Excellent visual design skills with a keen eye for detail, typography, color, and layout.
Ability to connect diverse user groups and industry workflows to create simplified design solutions.
Experience in conducting user research and incorporating user feedback into design iterations.
Proven experience in managing design projects from conception to launch.
Strong understanding of high-level layout patterns, UI elements, and navigation patterns.

Preferred Skills:

Experience with design systems and component libraries.
Familiarity with front-end development concepts (HTML, CSS, JavaScript) to facilitate collaboration with engineers.
Experience in a fast-paced startup environment or high-growth tech company.
Familiarity with AI-powered applications or the automotive industry.
Experience facilitating product discovery workshops and brainstorming sessions.
Ability to design and interpret results from A/B tests.

📝 Enhancement Note: The required skills emphasize hands-on proficiency with industry-standard tools like Figma and a deep understanding of mobile design principles. The "Lead" title, combined with the experience requirement, suggests a candidate who can not only execute but also guide and influence design strategy and process within the team.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

A strong, curated portfolio demonstrating end-to-end product design experience, showcasing shipped products and design process.
Case studies that detail problem definition, user research, design exploration (sketches, wireframes, prototypes), iteration based on feedback, and final UI design.
Examples of how you have translated complex user needs and business requirements into elegant and intuitive user interfaces.
Demonstrations of your ability to create and maintain brand consistency and visual identity across different platforms.
Evidence of your proficiency with Figma, including complex component creation, prototyping, and collaborative workflows.

Process Documentation:

Case studies should clearly articulate the design process followed, highlighting contributions to user research, ideation, prototyping, user testing, and iterative refinement.
Showcase how you have managed design projects, including scoping, timeline management, and collaboration with cross-functional teams (Product Managers, Engineers, etc.).
Examples of contributions to or creation of design systems, style guides, or component libraries to ensure scalability and consistency.
Documentation of how user feedback and data (e.g., A/B test results) were integrated into the design process to drive improvements and impact.

📝 Enhancement Note: A robust portfolio is critical for this role. It should not only display visual design skills but also demonstrate a deep understanding of the UX process, problem-solving capabilities, and the ability to articulate design decisions and their impact. For a "Lead" role, showing experience in managing projects and influencing product direction through design is key.

💵 Compensation & Benefits

Salary Range: Based on industry benchmarks for a Lead Product Designer with 5-10 years of experience in San Francisco, California, the estimated salary range is typically between $150,000 to $200,000 annually. This range is subject to variation based on the candidate's specific experience, skills, and the company's compensation philosophy.

Benefits:

Competitive salary and potential for equity in a pre-IPO, well-funded startup.
Comprehensive health, dental, and vision insurance plans.
Generous paid time off (PTO) and holidays.
Opportunities for professional development, including training, conferences, and workshops.
Work in a dynamic, fast-paced environment with significant growth potential.
Be part of a mission-driven company aiming to disrupt a massive market.
Potential for impact on millions of users and contribution to a $10B business.

Working Hours: The standard full-time work week is approximately 40 hours. While the role is based in San Francisco, the remote status indicates flexibility for candidates within the United States, but specific on-site expectations would need clarification.

📝 Enhancement Note: Given the company's pre-IPO status and significant funding, expect a compensation package that may include a competitive base salary, strong benefits, and potentially valuable stock options or equity, reflecting the high-growth environment and the impact expected from a Lead Designer.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology / Automotive / Fintech / Insurance. Jerry.ai operates at the intersection of these sectors, leveraging technology to simplify car ownership. The market for car ownership optimization is estimated at $2T in the U.S., indicating a substantial opportunity for disruption and innovation.

Company Size: Approximately 200 employees across 7 countries. This indicates a mid-sized, rapidly scaling organization with a global presence, offering opportunities for diverse collaboration.

Founded: 2017. The company has a history of innovation and scaling, having grown significantly since its inception and achieving substantial revenue growth and customer acquisition.

Team Structure:

The Product Design team is currently small (3 designers) and aims to double in size, indicating a period of growth and team building.
The Lead Product Designer will report directly to the CEO, Art Agrawal, signifying high-level visibility and direct influence on product strategy.
The design team will collaborate closely with Product Managers, Engineers, and other cross-functional stakeholders to deliver product features.

Methodology:

Data-driven approach, utilizing AI and machine learning to power its services and improve customer experiences.
Focus on iterative development and continuous improvement, leveraging user feedback and A/B testing.
Emphasis on building a "super app" that integrates multiple services related to car ownership, requiring a holistic and interconnected design strategy.
Agile development methodologies are likely employed to manage the rapid pace of product development.

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

📝 Enhancement Note: The company culture is characterized by rapid growth, innovation, and a focus on solving real-world problems in a massive market. The direct reporting line to the CEO for the Lead Product Designer underscores the strategic importance of design within Jerry.ai.

📈 Career & Growth Analysis

Operations Career Level: This is a "Lead" position, indicating a senior individual contributor role. It requires a high degree of autonomy, ownership, and the ability to influence product direction and design strategy. The role is positioned to significantly impact the user experience of a product used by millions.

Reporting Structure: The Lead Product Designer reports directly to the CEO, Art Agrawal. This provides direct access to executive leadership and an opportunity to influence company-level product decisions. The designer will also work closely with Product Managers and other members of the foundational design team.

Operations Impact: The Lead Product Designer will have a direct and substantial impact on Jerry.ai's growth and success by shaping the user experience of its car ownership super app. This involves driving customer acquisition, retention, and engagement through intuitive and visually appealing design solutions that simplify complex processes for millions of users.

Growth Opportunities:

Skill Advancement: Opportunity to deepen expertise in mobile and web app design, potentially specializing in areas like AI-driven product features, design systems at scale, or user research methodologies.
Leadership Potential: As the design team grows, there may be opportunities to mentor junior designers, lead design initiatives, and potentially move into a Design Manager or Head of Design role in the future.
Career Progression: Contributing to a pre-IPO, high-growth company offers significant career acceleration, with the potential for advancement as the company scales and potentially goes public.
Strategic Influence: Direct exposure to CEO-level decision-making provides invaluable experience in product strategy and business development.

📝 Enhancement Note: The reporting structure to the CEO is a significant factor for career growth, offering unparalleled visibility and influence. The role is ideal for a designer looking to make a substantial impact and grow with a rapidly scaling tech company, with potential leadership opportunities emerging as the team expands.

🌐 Work Environment

Office Type: The job is listed as "TELECOMMUTE," with a primary location in San Francisco, California. This suggests a remote-first or hybrid work model, offering flexibility to candidates across the United States. However, the mention of San Francisco as a location might imply an expectation for some on-site collaboration or occasional team meetups.

Office Location(s): Primary listed location is San Francisco, California. The company also has employees across 7 countries, indicating a distributed workforce.

Workspace Context:

The role operates within a fast-paced, dynamic startup environment, fostering a culture of innovation and rapid iteration.
Collaboration is key, with designers working closely with Product Managers, Engineers, and other stakeholders.
Expect a tech-forward environment with access to modern design and collaboration tools.
The remote nature of the role necessitates strong self-discipline, proactive communication, and effective use of virtual collaboration platforms.

Work Schedule: The role is full-time, with an estimated 40 hours per week. While remote, the emphasis on collaboration and timely delivery in a startup context suggests a need for responsiveness and commitment to project deadlines.

📝 Enhancement Note: The "TELECOMMUTE" designation is crucial. Candidates should clarify the exact expectations regarding on-site presence or required in-office days if any, especially given the San Francisco location mention. The environment is likely highly collaborative but also demanding due to the startup's growth trajectory.

📄 Application & Portfolio Review Process

Interview Process:

Initial Screening: A brief call with a recruiter to assess basic qualifications, experience, and cultural fit. Candidates should be ready to articulate their interest in Jerry.ai and its mission.
Portfolio Review & Design Challenge: This is a critical stage. Candidates will present their portfolio, showcasing their design process and impact. A practical design challenge or take-home project may be assigned to evaluate problem-solving skills, design thinking, and execution within a specific timeframe.
Hiring Manager/CEO Interview: A deeper dive into design philosophy, leadership potential, strategic thinking, and how the candidate aligns with the company's vision and values. Expect questions related to past project successes, challenges, and how they approach collaboration.
Team/Cross-functional Interviews: Meetings with Product Managers, Engineers, and potentially other designers to assess collaboration style, communication skills, and ability to integrate into the existing team dynamics.

Portfolio Review Tips:

Curate Effectively: Select 3-5 of your strongest, most relevant case studies that demonstrate end-to-end product design impact, particularly in mobile/consumer apps.
Tell a Story: For each case study, clearly articulate the problem, your role, the process you followed, the key decisions you made, the challenges you overcame, and the measurable outcomes or impact of your design.
Highlight Figma Proficiency: Be prepared to walk through your Figma files, showcasing your organizational skills, component usage, prototyping capabilities, and design system thinking.
Focus on "Why": Explain the rationale behind your design decisions, linking them back to user needs, business goals, and data insights.
Quantify Impact: Whenever possible, use metrics (e.g., conversion rates, user satisfaction scores, task completion times) to demonstrate the success of your design solutions.

Challenge Preparation:

Understand the Product: Thoroughly research Jerry.ai, its mission, its current product offerings, and its target audience.
Embrace the Brief: If given a take-home challenge, carefully read and understand all requirements and constraints.
Think Strategically: Focus on solving the core problem presented, demonstrating user empathy, a clear design process, and well-reasoned solutions.
Prioritize Clarity: Structure your presentation logically, using visuals effectively and clearly articulating your thought process. Be prepared to defend your design choices.
Simulate the Environment: Practice presenting your work and explaining your process concisely, as if you were in a live interview setting.

📝 Enhancement Note: The interview process will heavily weigh the portfolio and demonstrated design process. Candidates should prepare to present their work comprehensively and articulate their strategic thinking, especially given the direct reporting line to the CEO.

🛠 Tools & Technology Stack

Primary Tools:

Figma: Explicitly required for all design work, including wireframing, prototyping, UI design, and potentially design system management.
Prototyping Tools: While Figma is specified, familiarity with other prototyping tools like InVision, Principle, or Adobe XD might be beneficial for specific workflows.
User Research Platforms: Tools for conducting remote usability testing, user interviews, and surveys (e.g., UserTesting.com, Lookback, Maze).
Collaboration Tools: Platforms like Slack, Zoom, Google Workspace, and potentially project management tools like Asana or Jira for team communication and workflow management.

Analytics & Reporting:

Product Analytics: Familiarity with tools like Amplitude, Mixpanel, or Google Analytics to understand user behavior, track feature adoption, and measure the impact of design changes.
A/B Testing Platforms: Experience with tools used for A/B testing UI variations to optimize user engagement and conversion rates.

CRM & Automation:

While not directly a design tool, understanding how CRM systems (like Salesforce, HubSpot) and marketing automation platforms function can provide context for user journey mapping and cross-functional collaboration with marketing and sales operations.

📝 Enhancement Note: Proficiency in Figma is non-negotiable. Beyond that, experience with user research and product analytics tools will be highly valued, as they enable data-informed design decisions and demonstrate an understanding of measuring design impact.

👥 Team Culture & Values

Operations Values:

User-Centricity: A deep commitment to understanding and serving the user, ensuring that every design decision prioritizes a positive and seamless user experience.
Innovation & Problem-Solving: A drive to tackle complex challenges in the automotive ownership space with creative, technology-driven solutions.
Data-Driven Decision Making: Reliance on user data, A/B testing results, and analytics to inform design strategy and validate design choices.
Collaboration & Egoslessness: A team environment where individuals work together openly, share feedback constructively, and prioritize collective success over individual recognition.
Impact & Growth: A focus on making a tangible impact on millions of users and contributing to the company's ambitious growth targets.

Collaboration Style:

Cross-functional Partnership: Designers are expected to work closely and collaboratively with Product Managers, Engineers, and potentially marketing and data teams, fostering a shared understanding of product goals and user needs.
Open Communication: Encouragement of transparent communication, regular feedback loops, and constructive critiques to refine designs and processes.
Agile & Iterative: A willingness to adapt to changing priorities, embrace iterative design cycles, and respond quickly to user feedback and market shifts.
Proactive Engagement: Designers are encouraged to be proactive in identifying opportunities, contributing ideas, and driving design initiatives forward.

📝 Enhancement Note: The emphasis on "egoless" collaboration and a data-driven approach suggests a team that values humility, open feedback, and objective decision-making. A proactive and collaborative mindset will be key to success in this environment.

⚡ Challenges & Growth Opportunities

Challenges:

Scaling Design: As the company grows from 5M to 50M users, the design team will face the challenge of scaling design systems, processes, and user support to meet increased demand while maintaining quality.
Complexity of "Super App": Integrating multiple car ownership services into a single, cohesive "super app" presents a significant design challenge in terms of information architecture, user flow, and consistent experience.
Rapid Iteration Pace: The fast-paced startup environment requires designers to be adaptable, efficient, and comfortable with rapid iteration and evolving priorities.
Balancing Innovation with Usability: Creating groundbreaking features while ensuring they remain intuitive and user-friendly for a broad audience requires careful balance.

Learning & Development Opportunities:

Advanced UX/UI Skills: Deepen expertise in mobile design patterns, complex user flows, and potentially specialized areas like AI-driven product design.
Design Leadership: Develop skills in mentoring, leading design initiatives, and influencing product strategy, with potential for future team leadership roles.
Industry Exposure: Gain experience in a high-growth tech company with significant funding, learning about scaling operations, product-market fit, and go-to-market strategies.
Cross-functional Collaboration: Enhance skills in working effectively with diverse teams, including engineering, product management, and executive leadership.

📝 Enhancement Note: This role offers significant opportunities for a designer to grow their skills and career within a rapidly scaling, innovative company. The challenges presented are typical of high-growth tech environments and provide excellent learning experiences.

💡 Interview Preparation

Strategy Questions:

"Describe a time you had to design a complex feature for a mobile app. What was the problem, your process, and what was the outcome?" (Focus on problem definition, user research, iterative design, and measurable impact.)
"How do you approach balancing user needs with business goals and technical constraints in your design process?" (Demonstrate strategic thinking and ability to find optimal solutions.)
"Walk us through your process for conducting user research and incorporating feedback into your designs. Can you provide an example?" (Highlight user empathy and data-driven iteration.)
"How do you ensure brand consistency and maintain a cohesive user experience across multiple product touchpoints?" (Showcase understanding of design systems and visual identity.)
"Describe your experience with Figma. What are some of your favorite features or workflows for efficient design?" (Be prepared to discuss specific Figma skills and best practices.)

Company & Culture Questions:

"What interests you about Jerry.ai and our mission to simplify car ownership?" (Research the company's mission, values, and recent news.)
"How do you handle constructive criticism or feedback on your designs from team members or stakeholders?" (Emphasize openness, collaboration, and a growth mindset.)
"Describe your ideal collaboration style with Product Managers and Engineers." (Highlight proactive communication, shared ownership, and mutual respect.)
"How do you stay updated on the latest design trends and technologies?" (Showcase continuous learning and passion for the field.)

Portfolio Presentation Strategy:

Structure: Organize your presentation logically, usually with an introduction to the company and role, followed by 2-3 detailed case studies, and concluding with your career aspirations.
Focus on Process: For each case study, clearly outline the problem statement, your specific role and contributions, the research methods used, the design iterations (showing evolution), key decisions, and the final outcomes/impact.
Quantify Impact: Use data and metrics whenever possible to demonstrate the success of your designs (e.g., increased conversion rates, improved user satisfaction, reduced task completion time).
Highlight Figma Skills: Be ready to share your screen and demonstrate specific Figma techniques, component usage, prototyping, or collaboration features.
Be Concise and Engaging: Practice your presentation to ensure it flows well and stays within the allotted time, keeping your audience engaged. Prepare for questions about your choices and challenges.

📝 Enhancement Note: Be prepared to discuss your design process in detail, demonstrating how you translate user needs and business goals into elegant solutions. Highlighting your experience with Figma and your ability to work collaboratively in a fast-paced environment will be crucial.

📌 Application Steps

To apply for this Lead Product Designer position:

Submit your application through the provided link on Ashby.
Portfolio Customization: Tailor your portfolio to highlight projects that demonstrate experience with consumer-facing mobile apps, end-to-end design processes, and proficiency with Figma. Prioritize case studies showing significant user impact or problem-solving.
Resume Optimization: Ensure your resume clearly articulates your years of experience, key skills (like UX Design, Visual Design, Prototyping, Figma), and quantifiable achievements relevant to product design. Use keywords from the job description.
Interview Preparation: Practice presenting your portfolio and design process, focusing on clarity, storytelling, and demonstrating how your work has driven measurable results. Prepare to discuss your approach to user research, collaboration, and handling feedback.
Company Research: Thoroughly research Jerry.ai, its mission, products, and recent achievements. Understand the car ownership market and how Jerry.ai aims to disrupt it. This will help you articulate your interest and align your answers with the company's vision.

⚠️ 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.

Lead Product Designer