Senior Product Designer (Remote)

📍 Job Overview

Job Title: Senior Product Designer Company: Jerry.ai Location: United States (Remote) Job Type: FULL_TIME Category: Product Design / GTM Operations Support Date Posted: July 28, 2025 Experience Level: 5-10 Years Remote Status: Fully Remote (US-based candidates preferred, with optional hubs)

🚀 Role Summary

• This role is pivotal in shaping the user experience for Jerry.ai's innovative consumer-facing platform, focusing on car and home ownership management.
• The Senior Product Designer will drive the end-to-end design process for new features, translating user needs and business objectives into intuitive and visually appealing interfaces.
• A key aspect involves contributing to and evolving Jerry.ai's cross-platform design system, ensuring consistency and scalability across mobile and web applications.
• This position offers a unique opportunity to influence the design culture and processes within a rapidly growing startup, working closely with leadership.

📝 Enhancement Note: While this is a Product Design role, it has significant overlap with GTM (Go-To-Market) operations by directly impacting the user acquisition, engagement, and retention strategies through the product's user experience. The emphasis on user data, iteration, and cross-functional collaboration aligns with operational excellence principles.

📈 Primary Responsibilities

• Lead the complete design lifecycle for new product features, from initial concept and user research through wireframing, prototyping, high-fidelity UI design, and post-launch iteration based on user data and A/B testing.
• Collaborate closely with Product Managers, Engineers, Data Scientists, and Marketing teams to conceptualize, validate, and refine product ideas, ensuring alignment with user needs and business goals.
• Define, maintain, and evolve Jerry.ai's visual design system, ensuring brand consistency and a cohesive user experience across all platforms (iOS, Android, Web).
• Conduct user research, usability testing, and analyze user feedback and product analytics to inform design decisions and drive continuous product improvement.
• Actively contribute to the operational aspects of the design function, including team rituals, documentation standards, and the selection and implementation of design tooling.
• Champion best practices in visual and interaction design, elevating the overall craft and quality of design output across the organization.
• Advocate for the user by translating complex problems within the car and home ownership space into simple, elegant, and effective design solutions.

📝 Enhancement Note: The responsibilities emphasize a blend of creative design execution and operational rigor, including data analysis for iteration, design system management, and process contribution. This indicates a need for a designer who can operate with a high degree of autonomy and strategic thinking, akin to an operations role focused on product excellence.

🎓 Skills & Qualifications

Education:

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

Experience:

• 5-10 years of professional experience in Product Design, UX/UI Design, or a similar role, with a strong portfolio showcasing end-to-end product design experience.
• Proven experience designing for consumer-facing digital products, preferably in a high-growth startup or tech environment.
• Demonstrated experience in evolving and maintaining design systems across multiple platforms.

Required Skills:

• Product Design Expertise: Deep understanding of user-centered design principles, product development lifecycles, and best practices in UX/UI design.
• Visual & Interaction Design: High visual standards with a strong portfolio demonstrating exceptional UI design, typography, and interaction design skills.
• Prototyping & Wireframing: Proficiency in creating detailed wireframes, user flows, and interactive prototypes to effectively communicate design concepts.
• Collaboration & Communication: Excellent verbal and written communication skills, with the ability to articulate design decisions, present work effectively, and collaborate cross-functionally with diverse teams.
• Figma Proficiency: Expert-level skills in Figma for design, prototyping, and collaboration.
• User-Centricity & Empathy: A genuine curiosity and deep empathy for users, with the ability to translate user needs and pain points into effective design solutions.

Preferred Skills:

• Platform Design Systems: Familiarity with iOS Human Interface Guidelines, Android Material Design, and best practices for web design systems.
• User Research & Testing: Experience conducting various forms of user research, including interviews, surveys, and usability testing.
• Data Analysis for Design: Ability to interpret user data, analytics, and A/B test results to inform and iterate on designs.
• Agile Development Environment: Experience working within agile or scrum methodologies.
• Problem-Solving in Ambiguity: Proven ability to thrive in fast-paced, ambiguous environments and tackle complex problems with creative solutions.

📝 Enhancement Note: The required skills highlight a need for a designer who understands not just the aesthetics but also the strategic and operational aspects of product development, including user data analysis and system thinking. The "Senior" title implies a level of autonomy and strategic contribution expected in operations roles.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Comprehensive Case Studies: Showcase 3-5 detailed case studies that demonstrate end-to-end product design ownership, from problem definition and user research to final solution and measured impact.
• Problem-Solution Framing: Clearly articulate the problem being solved, the target user, and the design process undertaken, highlighting how user needs and business objectives were met.
• Visual & Interaction Design Examples: Include high-fidelity mockups, interactive prototypes, and examples of user flows that highlight strong visual and interaction design skills.
• Design System Contribution: If applicable, include examples of contributions to or creation of design systems, demonstrating an understanding of scalability and consistency.
• Impact & Iteration: Quantify the impact of your design solutions using metrics (e.g., conversion rates, engagement, task completion time) and describe how designs were iterated upon based on feedback or data.

Process Documentation:

• While not a formal requirement for submission, candidates should be prepared to discuss their personal design process, including how they approach user research, ideation, prototyping, testing, and collaboration.
• Be ready to articulate how you contribute to improving design team processes, documentation, and tooling.

📝 Enhancement Note: The emphasis on quantifiable impact, iteration based on data, and contribution to design systems directly reflects operations thinking, where process efficiency and measurable outcomes are paramount. A portfolio demonstrating these aspects will be highly valued.

💵 Compensation & Benefits

Salary Range:

• Based on industry benchmarks for Senior Product Designers in the US with 5-10 years of experience, and considering Jerry.ai's funding and growth stage, a competitive salary range is estimated between $140,000 - $190,000 annually. This range is inclusive of base salary and potential bonuses, and can vary based on specific experience, location within the US, and negotiation.

Benefits:

• Competitive Salary and Stock Options: Offering a flexible cash vs. equity structure to accommodate individual circumstances and preferences.
• Fully Remote Work: Flexibility to work from anywhere in the United States, with optional access to hubs in San Francisco, New York, and Palo Alto.
• Comprehensive Health & Wellness: Robust benefits package including health, dental, and vision insurance, 401K match, and dedicated mental health support.
• Career Acceleration: Opportunities for significant career growth, high visibility with company leadership, mentorship programs, and substantial ownership and influence within the product development cycle.
• Generous PTO: Likely includes paid time off, holidays, and sick leave, though specific details are not provided.

Working Hours:

• Standard full-time hours are expected, approximately 40 hours per week. The fully remote nature offers flexibility in scheduling, but candidates should be prepared to align with team needs and collaborate effectively across different time zones within the US.

📝 Enhancement Note: Salary range is an estimate based on industry data for similar roles and experience levels in the US tech market. The benefits highlight a focus on employee well-being and professional development, aligning with attracting top talent in competitive fields.

🎯 Team & Company Context

🏢 Company Culture

Industry: Insurtech, Consumer Technology, FinTech (focus on simplifying car & home ownership) Company Size: Jerry.ai has grown significantly, serving over 5 million customers and raising substantial funding ($240M+). While specific employee count isn't provided, its rapid growth suggests a dynamic, fast-paced, and scaling environment. Founded: 2017, founded by serial entrepreneurs. This indicates a company with established leadership and a track record of innovation.

Team Structure:

• The design team is currently small, consisting of only two designers, including this role. This means the Senior Product Designer will have a significant impact on shaping the team's structure, processes, and culture.
• The role reports directly to the Cofounder & Head of Product, offering high visibility and direct access to leadership.
• Cross-functional collaboration is integral, with close working relationships expected with Product Management, Engineering, Data Science, and Marketing teams.

Methodology:

• Data-Driven Decisions: Emphasis on using user research, feedback, and product analytics to inform design choices and drive product iteration and optimization.
• Agile Development: Likely operates using agile methodologies, requiring adaptability and iterative design processes.
• Customer-Centricity: A strong focus on understanding and solving the real-world problems of everyday Americans related to car and home ownership.
• Innovation & Disruption: Aiming to disrupt massive markets ($2T car, $3T home) by building a unified, end-to-end platform.

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

📝 Enhancement Note: The small design team size is a critical factor, presenting an opportunity for the Senior Product Designer to not just execute but also to influence and build the design function. This requires a proactive, process-oriented approach similar to operations roles.

📈 Career & Growth Analysis

Operations Career Level: Senior Individual Contributor with potential for Design Lead or Managerial growth as the design team scales. This role offers significant ownership and influence, akin to a senior operations role focused on process ownership and strategic impact. Reporting Structure: Reports directly to the Cofounder & Head of Product. This provides a direct line to decision-makers and a clear understanding of strategic priorities. Operations Impact: The Senior Product Designer will have a direct impact on customer acquisition, engagement, retention, and overall user satisfaction through the product experience. Their work will be crucial in achieving Jerry.ai's ambitious growth targets and market disruption goals.

Growth Opportunities:

• Design Leadership: Opportunity to shape the design team's culture, processes, and best practices as the company scales. Potential to grow into a Design Lead or Manager role.
• Skill Specialization: Deepen expertise in areas like design systems, user research, or specific product domains (insurtech, fintech, consumer apps).
• Cross-Functional Exposure: Gain broad experience working across various departments, understanding business operations and strategic decision-making at a startup.
• Mentorship: Receive mentorship from founders and senior leadership, accelerating professional development.
• Impactful Projects: Work on large-scale problems with the potential to impact millions of users and shape the future of consumer asset management.

📝 Enhancement Note: The growth trajectory is steep, offering significant opportunities for individuals who can demonstrate operational excellence in design, process improvement, and strategic thinking. This mirrors the career path for high-performing individuals in operations.

🌐 Work Environment

Office Type: The company offers a hybrid approach with optional hubs in San Francisco, New York, and Palo Alto. However, the role is primarily fully remote, allowing employees to choose their work location within the United States. Office Location(s): Hubs are available in San Francisco, CA; New York, NY; and Palo Alto, CA. These locations offer optional co-working spaces and opportunities for in-person collaboration.

Workspace Context:

• Remote Collaboration: Expect a highly collaborative environment that leverages digital tools for communication, design reviews, and project management.
• Design Tooling: Access to industry-standard design tools, particularly Figma, will be essential for day-to-day work.
• Team Interaction: While remote, fostering strong relationships with the Product, Engineering, and Data teams will be key. This will likely involve regular virtual meetings, stand-ups, and design critiques.

Work Schedule:

• Primarily a 40-hour work week, with flexibility inherent in a remote setup. However, the need for cross-functional collaboration may require some alignment with core working hours for team meetings and synchronous communication.

📝 Enhancement Note: The emphasis on remote collaboration and digital tooling underscores the need for strong self-management, communication, and process adherence, similar to requirements in remote operations roles.

📄 Application & Portfolio Review Process

Interview Process:

• Application Review: Initial screening of resumes and portfolios. A strong portfolio showcasing relevant experience and impact is crucial.
• Hiring Manager/Product Lead Interview: A discussion focused on your background, design philosophy, experience with consumer products, and understanding of Jerry.ai's mission.
• Design Challenge/Portfolio Deep Dive: This may involve a take-home assignment or a live presentation and critique of your portfolio. Expect to walk through case studies, explaining your process, decisions, and the impact of your work.
• Cross-functional Interviews: Meetings with members of the Product, Engineering, and potentially Data or Marketing teams to assess collaboration skills and integration with other functions.
• Founder/Leadership Interview: A final conversation to assess cultural fit, strategic thinking, and overall alignment with the company's vision.

Portfolio Review Tips:

• Focus on Impact: Quantify the results of your design work whenever possible. Use metrics to demonstrate how your designs solved problems or achieved business goals.
• Tell a Story: Structure your case studies as narratives, clearly outlining the problem, your process, your role, the challenges, and the outcome.
• Show Your Process: Include wireframes, user flows, research insights, and iteration examples to demonstrate your design thinking.
• Highlight Collaboration: Mention how you worked with cross-functional teams and stakeholders.
• Tailor to Jerry.ai: If possible, show projects that demonstrate experience with consumer apps, financial services, or complex problem-solving in large markets.

Challenge Preparation:

• Be prepared for a design challenge that might involve improving an existing feature or designing a new one. Focus on a structured approach: understanding the problem, defining constraints, exploring solutions, and justifying your choices.
• Practice presenting your work clearly and concisely, anticipating questions about your design decisions and their rationale.

📝 Enhancement Note: The interview process emphasizes a deep dive into design process and measurable impact, mirroring the evaluation criteria for operations roles where problem-solving methodology and quantifiable results are key.

🛠 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.
• Prototyping Tools: While Figma is primary, familiarity with other prototyping tools (e.g., InVision, ProtoPie) might be beneficial.
• User Research Platforms: Experience with tools like UserTesting.com, Maze, Lookback, or similar platforms for conducting remote user research and usability testing.

Analytics & Reporting:

• Product Analytics Tools: Familiarity with tools like Amplitude, Mixpanel, Google Analytics, or similar platforms to analyze user behavior and product performance data.
• Data Visualization Tools: Understanding how to interpret data visualizations and potentially use tools like Tableau or Looker for insights.

CRM & Automation:

• While not directly a design tool, understanding how CRM systems (e.g., Salesforce) and marketing automation platforms influence the customer journey can be beneficial for context.

📝 Enhancement Note: Proficiency in Figma is non-negotiable. Experience with analytics tools is highly valued, as it demonstrates an operational mindset focused on data-driven decision-making and performance optimization within the product.

👥 Team Culture & Values

Operations Values:

• Customer Obsession: Deeply understanding and prioritizing the needs and pain points of users in the car and home ownership space.
• Data-Driven: Utilizing research, feedback, and analytics to inform all design decisions and measure impact.
• Ownership & Accountability: Taking full responsibility for feature design, from concept to launch and iteration, and contributing to the operational excellence of the design team.
• Collaboration & Transparency: Working effectively with cross-functional teams, sharing insights openly, and fostering a culture of constructive feedback.
• Innovation & Simplicity: Striving to create elegant, user-friendly solutions for complex problems in massive markets.

Collaboration Style:

• Cross-Functional Integration: Actively partnering with Product, Engineering, and Data teams to ensure cohesive product development.
• Iterative Feedback Loops: Engaging in regular design reviews and seeking input from stakeholders to refine designs.
• Knowledge Sharing: Contributing to the design team's collective knowledge base and helping to onboard new team members.
• Process Improvement: Proactively identifying opportunities to enhance design workflows, documentation, and tooling.

📝 Enhancement Note: The emphasis on customer obsession, data-driven approaches, ownership, and collaboration reflects a culture that values operational efficiency and measurable outcomes, aligning with the core tenets of revenue and sales operations.

⚡ Challenges & Growth Opportunities

Challenges:

• Scaling Design Systems: Evolving and maintaining a robust design system for a rapidly growing product across multiple platforms presents a significant challenge requiring meticulous organization and strategic thinking.
• Balancing Speed and Craft: Operating at "agency-style speed" while maintaining high craft standards and thorough user research requires efficient workflow management and prioritization.
• Ambiguity and Complexity: Navigating the complexity of the car and home ownership markets and working through ambiguous requirements demands strong problem-solving skills and adaptability.
• Building Design Culture: As one of the early designers, shaping the team's processes, rituals, and overall culture from the ground up is a rewarding but challenging endeavor.

Learning & Development Opportunities:

• Design Leadership: Direct exposure to founders and leadership offers unparalleled opportunities for mentorship and learning about strategic business operations.
• Cross-Disciplinary Learning: Opportunities to learn from Product Managers, Engineers, and Data Scientists, gaining a holistic understanding of product development and business strategy.
• Industry Disruption: Participating in the disruption of massive markets provides valuable experience in scaling and innovation.
• Skill Enhancement: Focused development on specific design skills or areas of expertise relevant to Jerry.ai's growth.

📝 Enhancement Note: The challenges are framed in a way that highlights opportunities for growth, particularly in areas of process optimization, strategic problem-solving, and leadership development, which are core to operations roles.

💡 Interview Preparation

Strategy Questions:

• Be prepared to discuss your approach to understanding user needs for complex financial/consumer products like car and home ownership.
• How do you balance user experience with business objectives and technical constraints?
• How would you approach building or evolving a design system for a rapidly scaling company?
• Describe a time you had to influence stakeholders with a design decision. What was your process?
• How do you measure the success of your designs, and what metrics do you focus on?

Company & Culture Questions:

• Research Jerry.ai's mission, products, and recent news. Understand their approach to simplifying car and home ownership.
• Be ready to articulate why you are passionate about this mission and how your skills align with Jerry.ai's goals.
• Discuss your experience working in startup environments and your comfort with ambiguity.
• How do you contribute to a positive and productive team culture, especially in a remote setting?

Portfolio Presentation Strategy:

• Structure: Organize your portfolio around 3-5 impactful case studies. For each, clearly define the problem, your role, your process, key decisions, challenges faced, and the quantifiable outcomes.
• Narrative: Tell a compelling story for each project. Explain why you made certain design choices and how they addressed the user's needs or business goals.
• Visuals: Showcase high-fidelity mockups and interactive prototypes. Ensure your visual design skills are clearly represented.
• Process: Include sketches, wireframes, user flows, and research findings to illustrate your design thinking process.
• Impact: Dedicate a section to the results and impact of your work using metrics. Be prepared to discuss how you measured success and iterated based on data.
• Conciseness: Aim for clear, concise presentations. Practice your talking points to ensure you can deliver your message effectively within the allotted time.

📝 Enhancement Note: Interview preparation should focus on demonstrating not just design skills but also a strategic, data-driven, and process-oriented mindset, aligning with the expectations for senior operations professionals.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the provided link (jobs.ashbyhq.com).
• Portfolio Customization: Ensure your portfolio highlights projects demonstrating end-to-end design ownership, user-centric problem-solving, and quantifiable impact. Tailor your case studies to showcase experience relevant to consumer-facing products and complex markets.
• Resume Optimization: Craft your resume to emphasize achievements related to product design strategy, process improvement, cross-functional collaboration, and data-driven decision-making. Use keywords like "Product Design," "UX/UI," "Figma," "Design Systems," "User Research," and "Data Analysis."
• Interview Preparation: Practice articulating your design process, justifying your design decisions with user insights and business goals, and preparing specific examples of your impact. Be ready to present your portfolio confidently and answer questions about your experience in ambiguous environments.
• Company Research: Thoroughly research Jerry.ai's mission, values, and product offerings. Understand their market position and growth strategy to better align your responses during interviews and demonstrate genuine interest.

⚠️ 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.