Senior Product Designer (Remote) at Jerry.ai

📍 Job Overview

Job Title: Senior Product Designer (Remote) Company: Jerry.ai Location: San Francisco, California, United States (Remote) Job Type: FULL_TIME Category: Product Design / GTM Operations Strategy Date Posted: August 11, 2025 Experience Level: 5-10 Years (Senior Level) Remote Status: Fully Remote (United States)

🚀 Role Summary

Drive the end-to-end product design lifecycle for Jerry.ai's consumer-facing platform, focusing on car and home ownership management.
Contribute to shaping the design culture and processes within a growing, small design team, working closely with leadership.
Leverage data, user research, and testing to inform design decisions and iterate on features for a rapidly scaling user base.
Develop and maintain a cohesive visual design system across mobile and web platforms to ensure a consistent and high-quality user experience.
Collaborate cross-functionally with product, engineering, and data teams to translate complex problems into intuitive and impactful design solutions.

📝 Enhancement Note: While this is a Product Design role, the emphasis on "shaping the future of car and home ownership," "serving our next 50 million users," and the "massive market" suggests a significant strategic component. The role will likely involve understanding Go-To-Market (GTM) implications of design decisions, ensuring user experience aligns with business objectives, and contributing to the operational efficiency of the design process itself, making it relevant to GTM Operations Strategy.

📈 Primary Responsibilities

Own the complete design process for new features and product enhancements, from initial concept, user flows, wireframing, and prototyping to high-fidelity UI design and final asset delivery.
Conduct user research, usability testing, and analyze user feedback and performance data to identify opportunities for design improvement and validate design solutions.
Collaborate closely with Product Managers to define product requirements, explore design solutions, and ensure alignment with business goals and user needs.
Partner with Engineering teams to ensure accurate implementation of designs, troubleshoot technical constraints, and maintain design integrity throughout the development cycle.
Contribute to the evolution and maintenance of Jerry.ai's design system, ensuring consistency, scalability, and adherence to best practices across all product touchpoints.
Elevate the overall design craft and user experience by establishing and advocating for high visual and interaction design standards.
Participate in defining and refining design team rituals, documentation practices, and tooling to optimize workflow efficiency and collaboration.

📝 Enhancement Note: The responsibility to "raise the bar for craft" and "define and evolve our visual design system" implies a strategic contribution to the company's design operations, ensuring consistency and efficiency in design output. This aligns with operational excellence in design execution.

🎓 Skills & Qualifications

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

Experience: 5-10 years of professional experience in product design, with a strong portfolio showcasing end-to-end design ownership for consumer-facing digital products.

Required Skills:

Proven expertise in user-centered design principles and methodologies.
High visual design standards with a keen eye for detail, typography, and layout.
Proficiency in industry-standard design and prototyping tools, with a strong emphasis on Figma.
Experience in developing and maintaining comprehensive design systems across multiple platforms (mobile, web).
Strong understanding of user research techniques, usability testing, and data analysis to inform design decisions.
Excellent collaboration and communication skills, with the ability to articulate design rationale effectively to cross-functional teams and stakeholders.
Experience working in fast-paced, agile environments and comfortable with ambiguity.
Demonstrated ability to design for complex problems and deliver intuitive user experiences.

Preferred Skills:

Experience with consumer fintech or property management related products.
Familiarity with front-end development concepts (HTML, CSS, JavaScript) to better collaborate with engineering.
Experience mentoring junior designers or contributing to design team processes.
Familiarity with A/B testing methodologies for design optimization.
Experience in a startup environment with a focus on rapid iteration and growth.

📝 Enhancement Note: The requirement for "agency-style speed" and "broader ownership" suggests a need for designers who can manage projects autonomously and adapt quickly, reflecting a need for operational agility within the design function. The emphasis on "curious, thoughtful, and deeply empathic" points to a candidate who can not only execute but also contribute to the strategic understanding of user needs, which is crucial for GTM alignment.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

Showcase a minimum of 3-5 distinct product design projects, demonstrating end-to-end ownership from problem identification to launched solution.
Projects should highlight your process, including user research, ideation, wireframing, prototyping, UI design, and post-launch iteration based on data.
Clearly articulate the problem statement, your role, design challenges, solutions, and the impact of your work, ideally with quantifiable results.
Include examples of your contribution to or creation of design systems, showcasing consistency and scalability.
Demonstrations of mobile (iOS/Android) and web design expertise are highly valued.

Process Documentation:

Be prepared to discuss your design process in detail, including how you approach user research, concept validation, and iterative design based on feedback and data.
Examples of how you've collaborated with product, engineering, and data teams to bring designs to life.
Ability to articulate how you contribute to team rituals, documentation, and tooling to improve design operations and efficiency.
Evidence of how you raise the bar for design craft and advocate for user-centric solutions within a team.

📝 Enhancement Note: The expectation to "Contribute to how design operates — from team rituals to documentation and tooling" and "Raise the bar for craft" indicates a need for a portfolio that not only showcases design output but also demonstrates an understanding of design operations and process improvement. This is key for candidates looking to influence the operational framework of the design team.

💵 Compensation & Benefits

Salary Range: Given the Senior Product Designer title, 5-10 years of experience, and a remote role in the US, a competitive salary range is expected. Based on industry benchmarks for similar roles in tech hubs like San Francisco and for fully remote positions across the US, the estimated annual base salary range would be $140,000 - $180,000. This range can vary based on specific experience, skills, and the candidate's location within the US.

Benefits:

Competitive salary and stock options, with a flexible cash vs. equity structure to accommodate individual circumstances and preferences.
Fully remote work environment, allowing for flexibility and work-life balance.
Comprehensive benefits package including:
- 401K match to support retirement savings.
- Health, dental, and vision insurance for medical well-being.
- Mental health support to promote overall wellness.
Accelerated career growth opportunities with high visibility to leadership, mentorship programs, and significant ownership and influence within the company.

Working Hours: The standard working hours are typically 40 hours per week, aligning with full-time employment. However, the fully remote nature and startup environment may offer some flexibility in scheduling to accommodate different time zones and personal needs, provided core responsibilities and collaboration with teams are met.

📝 Enhancement Note: The mention of "flexible cash vs. equity structure" is a significant perk for senior roles and indicates the company's willingness to tailor compensation packages. The "accelerated career growth" with "high visibility with leaders" suggests a dynamic environment where operational contributions are recognized and can lead to faster advancement.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology (Fintech/Consumer Services) - Jerry.ai operates in the massive, multi-trillion dollar markets of car and home ownership, aiming to simplify these complex areas through technology and AI. This positions them at the intersection of Insurtech, Fintech, and Consumer SaaS.

Company Size: Jerry.ai is a growing startup, having achieved significant revenue growth (60X in 6 years) and raised substantial funding ($240M). While the exact current employee count isn't provided, the mention of a "small team" of designers (2 today) suggests an overall company size that is likely between 50-200 employees, characteristic of a scaling startup. This size offers opportunities for high impact and broad ownership.

Founded: Founded in 2017, Jerry.ai has a history of innovation and growth in a short period, demonstrating a strong track record and ambition to disrupt traditional markets.

Team Structure:

Design Team: Currently small (2 designers), providing a unique opportunity for a Senior Product Designer to significantly influence the team's direction, processes, and culture. You'll report to the Cofounder & Head of Product.
Cross-functional Collaboration: Expect close collaboration with Product Management, Engineering (likely agile teams), Data Science/Analytics, Marketing, and potentially Customer Support teams. The design function is integral to the product development lifecycle.

Methodology:

Data-Driven: The company emphasizes using "real user data," "user feedback," and "testing" to refine designs, indicating a strong reliance on analytics and user insights.
Agile & Iterative: The startup environment and focus on rapid growth suggest an agile development methodology with frequent iterations and a continuous improvement mindset for product and design.
Process Optimization: The role explicitly mentions contributing to "how design operates — from team rituals to documentation and tooling," highlighting a focus on optimizing the design workflow and operational efficiency.

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

📝 Enhancement Note: The "small team, just 2 designers today" is a critical piece of information. It implies a significant opportunity for a Senior Product Designer to not just execute but also to mentor, shape processes, and build the design function from the ground up, making it a highly influential role in terms of design operations and team development.

📈 Career & Growth Analysis

Operations Career Level: Senior Product Designer. This level signifies a high degree of autonomy, expertise, and the ability to lead design initiatives. It involves not only execution but also strategic thinking, process contribution, and potentially mentoring. The role is critical in translating business objectives into user-centric product experiences.

Reporting Structure: The Senior Product Designer will report directly to the Cofounder & Head of Product. This close proximity to leadership provides high visibility and direct impact on strategic decisions.

Operations Impact: The design of Jerry.ai's platform has a direct impact on user acquisition, engagement, retention, and ultimately, revenue. By simplifying complex financial decisions related to car and home ownership, effective design can drive customer adoption, reduce churn, and enhance the company's ability to serve its massive target market, thereby contributing significantly to GTM success and overall business growth.

Growth Opportunities:

Design Leadership: Opportunity to grow into a Design Lead or Manager role as the design team expands.
Product Strategy: Influence product direction and strategy through design insights and user advocacy.
Skill Development: Deepen expertise in consumer-facing platforms, design systems, and potentially new areas as Jerry.ai expands its offerings.
Mentorship: Gain experience mentoring junior designers and establishing best practices for the design team.
Company Growth: Participate in scaling a high-growth consumer tech company with significant market disruption potential.

📝 Enhancement Note: The direct reporting line to a Cofounder & Head of Product is an exceptional growth opportunity. It suggests that this role is not just about design execution but also about contributing to the operational strategy of the product organization and the overall GTM approach through design leadership.

🌐 Work Environment

Office Type: The company offers a hybrid work model with optional in-office hubs in San Francisco, New York, and Palo Alto. However, the "Fully remote work" designation for this specific role means candidates are not required to be near an office.

Office Location(s): While the role is remote, the company has physical hubs in San Francisco, CA; New York, NY; and Palo Alto, CA. There's also a mention of Toronto, Canada, suggesting potential for a distributed team.

Workspace Context:

Remote Collaboration: Expect a highly collaborative remote environment that relies on digital tools for communication, project management, and design collaboration.
Tech-Enabled: Access to modern design and communication tools is expected, facilitating seamless interaction with distributed teams.
Autonomy & Flexibility: The remote setup emphasizes autonomy and flexibility, requiring self-discipline and proactive communication.

Work Schedule: While a standard 40-hour work week is implied, the remote nature may offer flexibility in daily scheduling, allowing individuals to structure their workdays around core collaboration hours and personal needs, which is beneficial for deep work and focused design activities.

📝 Enhancement Note: The "Fully remote work with hubs in San Francisco, New York, Toronto, Palo Alto (in-office optional)" indicates a distributed-first culture. For a Senior Product Designer, this means establishing robust remote collaboration workflows and contributing to the operational framework that supports a distributed design team.

📄 Application & Portfolio Review Process

Interview Process:

Application Screening: Review of resume and portfolio for relevant experience, skills, and design quality.
Hiring Manager/Product Lead Chat: An initial conversation to discuss your background, motivations, and assess cultural fit. This may include a brief overview of the role and team.
Design Portfolio Presentation & Discussion: A more in-depth session where you present your portfolio, discussing 2-3 key projects. Expect to detail your process, problem-solving approach, design decisions, and impact. This is where your operational understanding of design processes will be evaluated.
Cross-functional Collaboration Exercise/Interview: You might be asked to collaborate with a Product Manager or Engineer on a small design challenge or discuss how you would approach a specific product problem, assessing your collaboration and problem-solving skills.
Founder/Senior Leadership Interview: A final conversation to assess strategic thinking, cultural alignment, and overall fit with the company's mission and vision.

Portfolio Review Tips:

Structure for Impact: Organize your portfolio logically, starting with a strong overview of each project. Clearly define the problem, your role, the process, your specific contributions, the solution, and the measurable outcomes.
Showcase Process, Not Just Polish: Highlight your design thinking, problem-solving methodologies, and how you iterate based on data and feedback. This demonstrates your operational approach to design.
Quantify Results: Whenever possible, include metrics that demonstrate the impact of your designs (e.g., increased conversion rates, reduced support tickets, improved user satisfaction scores). This ties your work to business operations.
Design System Contribution: If you have experience building or contributing to design systems, dedicate a section to showcase this, explaining your approach to scalability and consistency.
Tailor to Jerry.ai: Research Jerry.ai's products and mission. Frame your projects and discussions to highlight how your skills and experience align with their goals, particularly in simplifying car and home ownership.

Challenge Preparation:

Problem-Solving: Be prepared for hypothetical design challenges. Think about how you would approach understanding the problem, gathering information, ideating solutions, and validating them, demonstrating your structured thinking and operational approach.
System Thinking: Consider how your designs integrate with existing systems and user workflows. Show an understanding of the broader product ecosystem.
Communication: Practice articulating your design decisions clearly and concisely, especially when explaining trade-offs and user-centric justifications.

📝 Enhancement Note: The emphasis on "how design operates" and "team rituals to documentation and tooling" suggests that interviewers will be looking for candidates who not only design well but also understand the operational aspects of a design team and how to optimize them. This includes how to collaborate effectively, document processes, and contribute to a scalable design function.

🛠 Tools & Technology Stack

Primary Tools:

Figma: Explicitly mentioned as a required skill, signifying its central role in design creation, prototyping, and collaboration.
Prototyping Tools: While Figma is primary, familiarity with other tools like InVision, Principle, or Adobe XD might be beneficial for specific use cases.
Design System Management: Tools or methodologies for managing and scaling design systems (e.g., Zeroheight, Storybook integration).

Analytics & Reporting:

User Analytics Platforms: Experience with tools like Amplitude, Mixpanel, Google Analytics, or similar platforms to understand user behavior and measure design impact.
A/B Testing Tools: Familiarity with tools like Optimizely, VWO, or in-house A/B testing frameworks to validate design hypotheses.
Data Visualization Tools: Ability to interpret data presented in dashboards (e.g., Tableau, Looker) to inform design decisions.

CRM & Automation:

While not directly a designer's tool, understanding how CRM systems (like Salesforce) and marketing automation platforms influence user journeys and data collection can be beneficial for holistic product design.

📝 Enhancement Note: The implicit need to "use research, user feedback, and testing" and "use real user data" points to a requirement for designers to be comfortable with data analysis tools and methodologies. Understanding how to leverage analytics to improve designs is a key operational skill for a Senior Product Designer.

👥 Team Culture & Values

Operations Values:

User-Centricity: A deep empathy for users and a commitment to solving their real-world problems related to car and home ownership.
Impact-Driven: Focus on delivering tangible results and driving business growth through design, with an emphasis on measurable outcomes.
Collaboration: Strong teamwork and open communication across product, engineering, and data teams to achieve shared goals.
Craftsmanship & Quality: A commitment to high standards in visual design, interaction design, and overall user experience.
Curiosity & Learning: A proactive approach to learning, exploring new ideas, and adapting to a rapidly evolving market and technology landscape.
Ownership & Initiative: Taking responsibility for design outcomes and proactively identifying opportunities for improvement.

Collaboration Style:

Cross-functional Partnership: Working closely with Product Managers to define strategy and with Engineers to ensure feasible and high-quality implementation.
Open Feedback: A culture that encourages constructive feedback among designers and with cross-functional partners to elevate the quality of work.
Process-Oriented: Contributing to and improving design processes, documentation, and tooling to enhance team efficiency and output.

📝 Enhancement Note: The values emphasize not just individual design skill but also the ability to contribute to the operational health and effectiveness of the design team and its collaboration with other functions. This is crucial for a senior role aiming to influence the company's product development processes.

⚡ Challenges & Growth Opportunities

Challenges:

Shaping Design Processes: As part of a small, growing team, a challenge will be establishing and refining design workflows, documentation standards, and team rituals from the ground up.
Balancing Speed and Quality: Operating at "agency-style speed" while maintaining high design craft and system integrity requires efficient processes and strong decision-making.
Rapid Scaling: Designing for a rapidly growing user base (aiming for 50M+ users) and a complex, multi-faceted product suite (car and home) presents significant scalability challenges.
Ambiguity: Working in a fast-paced startup environment often involves ambiguity, requiring adaptability and the ability to define solutions with incomplete information.

Learning & Development Opportunities:

Influence Design Culture: Directly impact the formation and evolution of Jerry.ai's design culture and team practices.
Strategic Impact: Gain experience contributing to product strategy and GTM decisions through design leadership.
Cross-Disciplinary Exposure: Work closely with founders and leaders across product, engineering, and data, broadening your understanding of business operations.
Market Disruption: Be part of a company disrupting massive, established markets, offering unique learning experiences in business strategy and growth.

📝 Enhancement Note: The challenges are framed as opportunities for growth, particularly in the operational aspects of building and scaling a design function within a high-growth startup. This aligns with the expectation that a senior hire will contribute to process improvement and team development.

💡 Interview Preparation

Strategy Questions:

"How would you approach designing a new feature for our car insurance product that aims to increase user engagement by 15%?" (Focus on user research, ideation, validation, and metrics.)
"Describe your process for creating or evolving a design system for a rapidly growing consumer product. What are the key operational considerations?" (Focus on scalability, consistency, documentation, and collaboration.)
"How do you balance user needs with business objectives and technical constraints in your design process?" (Focus on trade-offs, communication, and problem-solving.)
"Given that the design team is small, how would you contribute to establishing efficient design workflows and team rituals?" (Focus on process improvement, collaboration, and operational contribution.)

Company & Culture Questions:

"What interests you most about Jerry.ai's mission to simplify car and home ownership?" (Demonstrate research and alignment with company values.)
"Describe a time you worked in an ambiguous environment. How did you define clarity and drive progress?" (Assess adaptability and problem-solving.)
"How do you ensure your design work is user-centric and data-informed?" (Focus on research, testing, and analytics.)

Portfolio Presentation Strategy:

Narrative Flow: Structure your portfolio presentation as a story, guiding the interviewers through your design journey for each project.
Process Emphasis: Dedicate significant time to explaining your thought process, the "why" behind your decisions, and how you iterated based on feedback and data. This is where your operational approach to design shines.
Impact & Metrics: Clearly articulate the success of your projects using quantifiable data. If exact metrics aren't available, discuss anticipated impact and how you would measure it.
Systemic Thinking: If discussing design systems, explain your approach to governance, contribution workflows, and ensuring adoption across teams.
Conciseness: Be mindful of time. Practice your presentation to ensure you cover key points efficiently and effectively.

📝 Enhancement Note: Interview preparation should focus on demonstrating not just design skills but also an understanding of operational efficiency within a design context, process ownership, cross-functional collaboration, and the ability to contribute to a growing team's structure and culture.

📌 Application Steps

To apply for this Senior Product Designer position:

Submit your application through the provided Ashby link.
Portfolio Customization: Ensure your portfolio prominently features projects that showcase end-to-end ownership, problem-solving, and design system contributions. Tailor the presentation to highlight your understanding of user-centric design and data-driven iteration.
Resume Optimization: Highlight relevant experience with consumer-facing products, Figma proficiency, design system work, and any experience contributing to design processes or team operations. Quantify achievements where possible.
Interview Preparation: Practice articulating your design process, methodologies, and the impact of your work. Be ready to discuss how you would contribute to shaping the design team's culture and operational efficiency.
Company Research: Understand Jerry.ai's mission, market position, and growth trajectory. Consider how your design philosophy aligns with their goal of simplifying car and home ownership for millions of Americans.

⚠️ 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.

Senior Product Designer (Remote)