Head of Design

📍 Job Overview

Job Title: Head of Design Company: Jerry.ai Location: San Francisco, California, United States Job Type: FULL_TIME Category: Design Operations / Product Design Leadership Date Posted: August 11, 2025 Experience Level: 5-10 Years (Mid-Senior to Senior) Remote Status: Fully Remote (with optional hubs)

🚀 Role Summary

• Lead the end-to-end product design process for Jerry.ai's mobile and web platforms, encompassing discovery, ideation, prototyping, UI design, and post-launch iteration.
• Establish and cultivate a world-class design culture focused on speed, thoughtfulness, and user-centricity, while setting a high bar for design excellence.
• Drive cross-functional collaboration with Product, Engineering, and Data teams to translate user insights and business objectives into intuitive and impactful product experiences.
• Develop and manage a high-performing design team, fostering growth through mentorship, feedback, and strategic hiring, while establishing scalable design processes and tools.

📝 Enhancement Note: While the provided title is "Head of Design," the responsibilities heavily emphasize hands-on product design leadership, team building, and process establishment. This suggests a role that is both strategic and deeply tactical, requiring a leader who can execute as well as guide. The "0 to 1" aspect indicates a significant opportunity to shape the design function from its foundational stages.

📈 Primary Responsibilities

• Product Design Ownership: Lead the design of product features across Jerry.ai's mobile (iOS, Android) and web surfaces, from initial concept exploration and user flows to wireframing, prototyping, high-fidelity UI design, and iterative refinement based on user feedback and data.
• Design Excellence & Culture: Define and champion design standards, ensuring exceptional quality in visual design, interaction design, and overall user experience. Foster a collaborative and iterative design culture that encourages experimentation, learning, and a strong focus on usability.
• Cross-Functional Partnership: Collaborate closely with Product Management, Engineering, and Data Science teams to explore new opportunities, validate hypotheses through user research and A/B testing, and ensure seamless delivery of design solutions.
• User-Centricity & Data Leverage: Utilize user research methodologies (qualitative and quantitative) and behavioral data analytics to deeply understand user needs, identify pain points, and inform design decisions, leading to continuous improvement of existing and new features.
• Design System Evolution: Drive the development, maintenance, and expansion of Jerry.ai's visual design system and component libraries across all platforms, ensuring consistency, scalability, and efficiency in design and development.
• Team Building & Mentorship: Recruit, onboard, mentor, and manage a small but high-performing team of product designers. Elevate the design quality and impact across the organization through effective feedback, training, and knowledge sharing.
• Process & Operations: Establish and refine scalable design processes, workflows, and best practices to support the design team's growth and ensure efficient, high-quality output. Implement and manage design tools and technologies that enhance productivity and collaboration.

📝 Enhancement Note: The responsibilities highlight a dual focus on individual contribution ("hands-on design work") and team leadership ("build a world-class design team"). The emphasis on "0 to 1" and establishing "scalable design processes" indicates a need for someone comfortable with ambiguity and foundational work, common in early-stage, high-growth companies.

🎓 Skills & Qualifications

Education:

• Bachelor's or Master's degree in Design, HCI, Computer Science, or a related field, or equivalent practical experience.

Experience:

• Proven track record of successfully leading product design initiatives for consumer-facing digital products, with a strong emphasis on mobile and web platforms.
• Experience in high-growth technology environments or startups, demonstrating an ability to adapt quickly and thrive in fast-paced, evolving landscapes.
• Demonstrated experience in building, mentoring, and managing design teams, including hiring and performance management.

Required Skills:

• Exceptional Visual & Interaction Design: Mastery in crafting intuitive, engaging, and aesthetically pleasing user interfaces and seamless interaction flows.
• Hands-On Design Execution: Proficiency in using design tools such as Figma for wireframing, prototyping, UI design, and component library management.
• User Research & Data Analysis: Ability to conduct user research, analyze behavioral data, and translate insights into actionable design improvements.
• Design Leadership & Strategy: Capability to set design vision, define design principles, and develop strategic design roadmaps aligned with business objectives.
• Cross-Functional Collaboration: Proven ability to partner effectively with Product Managers, Engineers, Data Scientists, and Marketing teams.
• System Thinking: Experience in developing and scaling design systems and component libraries for consistency and efficiency.
• Mentorship & Team Development: Demonstrated ability to mentor designers, provide constructive feedback, and foster a positive and productive team environment.
• Agile & Iterative Methodologies: Familiarity with agile development processes and a strong iterative design approach.

Preferred Skills:

• Experience with multi-platform design (iOS, Android, Web) and understanding of platform-specific design patterns.
• Familiarity with customer relationship management (CRM) tools and their integration with user experience.
• Knowledge of automation tools and their application in streamlining design workflows.
• Experience in the FinTech, InsurTech, or real estate technology sectors.

📝 Enhancement Note: The emphasis on "hands-on design leader who still loves to design" and "exceptional visual and interaction design skills" points towards a need for a senior individual contributor who can also lead. The mention of "0→1 opportunities" and "navigating ambiguity" further reinforces the expectation of a proactive, self-starter mentality.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Product Design Case Studies: Showcase at least 3-5 comprehensive case studies demonstrating end-to-end product design ownership for complex consumer-facing features or products. Each case study should clearly articulate the problem, your role, the design process, key decisions, and the impact of your work.
• Visual & Interaction Design Excellence: Highlight a strong portfolio of visual design examples, including UI mockups, style guides, and detailed interaction flows that demonstrate a keen eye for detail and aesthetic quality.
• System Design & Scalability: Include examples of contributions to or creation of design systems, component libraries, or style guides, illustrating an understanding of scalability, consistency, and maintainability.
• User Research & Data Integration: Demonstrate how user research, data analysis, or A/B testing informed your design decisions and led to measurable improvements in user experience or business outcomes.
• Leadership & Team Impact: If applicable, include examples of leadership, mentorship, or process improvements that positively impacted a design team or product development cycle.

Process Documentation:

• Workflow Design & Optimization: Portfolio pieces should implicitly or explicitly demonstrate your ability to design and optimize user workflows, ensuring efficiency and clarity.
• System Implementation Standards: Showcase how you've applied design systems and component libraries to ensure consistent and scalable product development.
• Measurement & Performance Analysis: Provide evidence of how your design work has been measured against key performance indicators (KPIs) and how you've used data to iterate and improve.

📝 Enhancement Note: Given the "0 to 1" nature of building the design team and processes, the portfolio should not only showcase individual design craft but also the ability to define and implement design operations, including system thinking and process maturation.

💵 Compensation & Benefits

Salary Range: Based on industry standards for a Head of Design role in San Francisco/Bay Area with 5-10 years of experience, including leadership responsibilities, the estimated salary range is $180,000 - $250,000 per year. This range is subject to adjustment based on the candidate's specific experience, skills, and location.

Benefits:

• Competitive Salary and Stock Options: Offers a flexible cash vs. equity structure, allowing candidates to tailor their compensation package.
• Fully Remote Work: Employees can work from anywhere in the United States or Canada, with optional hubs available in San Francisco, New York, and Palo Alto.
• Comprehensive Benefits Package: Includes 401K matching, robust health, dental, and vision insurance, and mental health support.
• Professional Development: Opportunities for growth and learning within a rapidly expanding company.

Working Hours:

• Standard full-time hours are expected, likely around 40 hours per week. However, given the leadership role and startup environment, flexibility and a commitment to achieving goals are paramount. The fully remote nature may offer some flexibility in structuring the workday, but responsiveness and collaboration across time zones will be important.

📝 Enhancement Note: The salary estimate is derived from industry benchmarks for senior design leadership roles in high-cost-of-living areas like San Francisco, considering the company's funding and growth trajectory. The "flexible cash vs equity structure" is a significant perk that allows for personalized compensation planning.

🎯 Team & Company Context

🏢 Company Culture

Industry: InsurTech / Consumer Technology / Fintech Company Size: Growing rapidly, currently has a small but growing design team (2 designers mentioned). Overall company size is implied to be scaling from its 2017 founding, with over 5 million customers and significant funding ($240M raised). Founded: 2017

Team Structure:

• The Head of Design will report directly to the Cofounder & Head of Product, indicating a high level of visibility and direct access to leadership.
• The initial design team is small (currently 2 designers), providing an opportunity for the Head of Design to build and shape the team from the ground up.
• Collaboration is expected to be close-knit and cross-functional, involving Product, Engineering, and Data teams.

Methodology:

• Data-Driven Product Development: Emphasizes leveraging user research and behavioral data to inform design decisions and product iterations.
• Agile & Iterative Approach: The mention of shipping fast and testing hypotheses suggests an agile development methodology with a strong focus on iterative design and continuous improvement.
• "0 to 1" Mentality: The company is looking for individuals comfortable with building new functions, processes, and teams from scratch.
• Mission-Oriented: A strong focus on helping "everyday Americans" manage their finances and major assets (car, home).

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

📝 Enhancement Note: The company's mission to simplify complex financial and ownership tasks for a broad consumer base is a key cultural driver. The "super app" approach for car and home ownership suggests a focus on integration, user convenience, and comprehensive solutions.

📈 Career & Growth Analysis

Operations Career Level: Lead / Principal / Managerial (Design Leadership) Reporting Structure: Reports directly to the Cofounder & Head of Product. Will likely manage a small team of 2-4 designers initially, with potential for team expansion. Operations Impact: As Head of Design, this role has a direct and significant impact on user acquisition, engagement, retention, and overall product success. By shaping user experience and driving design excellence, the role directly contributes to revenue growth and market positioning.

Growth Opportunities:

• Team Building & Leadership: Opportunity to build a world-class design team from the ground up, defining its structure, processes, and culture.
• Strategic Influence: Direct collaboration with founders and leadership provides a platform to influence product strategy and company direction.
• Market Disruption: Play a pivotal role in disrupting massive ($5T+) markets (car and home ownership) with a unique, unified platform.
• Skill Advancement: Develop expertise in leading design for consumer-focused "super apps" and scaling design operations in a high-growth environment.
• Career Progression: Potential to grow into a VP of Design or similar senior leadership role as the company scales.

📝 Enhancement Note: The "0 to 1" nature of building the design function means this role offers substantial opportunity for leadership growth and direct impact on company trajectory, appealing to ambitious design leaders.

🌐 Work Environment

Office Type: Hybrid/Optional Hubs: While fully remote is the primary offering, Jerry.ai maintains optional hubs in San Francisco, New York, and Palo Alto. This suggests a flexible work environment that supports remote collaboration but also provides physical spaces for optional in-person interaction or focused work. Office Location(s): San Francisco, CA; New York, NY; Palo Alto, CA; Toronto, Canada (remote-friendly).

Workspace Context:

• Remote-First Culture: The company supports a fully remote work arrangement, emphasizing asynchronous communication and digital collaboration tools.
• Collaborative Digital Environment: Expect a culture that relies heavily on digital tools for communication, design collaboration (e.g., Figma), and project management.
• Cross-Functional Interaction: Opportunities to engage with product, engineering, and data teams through virtual meetings, shared documentation, and collaborative platforms.
• Focus on Efficiency: The emphasis on "speed, thoughtfulness, and usability" implies a work environment that values efficient processes and high-quality output.

Work Schedule:

• Standard full-time working hours are expected. Given the remote nature and potential for international team members (e.g., Toronto), flexibility in scheduling may be present, but effective communication across time zones will be key. Emphasis on delivering results over strict adherence to hours.

📝 Enhancement Note: The "fully remote" aspect with optional hubs offers flexibility. The success of this environment relies heavily on strong communication protocols, digital collaboration tools, and a self-motivated workforce.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Likely a brief call with a recruiter to assess basic qualifications and cultural fit.
• Hiring Manager Interview: In-depth discussion with the Cofounder & Head of Product, focusing on leadership experience, design philosophy, strategic thinking, and motivations.
• Portfolio Review & Design Challenge: A presentation of your portfolio, likely including a specific design challenge or case study discussion related to Jerry.ai's product. This is where you'll demonstrate your hands-on skills, process, and strategic thinking.
• Cross-Functional Interviews: Interviews with key stakeholders from Product, Engineering, and Data to assess collaboration skills and technical understanding.
• Team Interviews: Potentially meet with existing designers or team members to evaluate cultural fit and team dynamics.
• Final Round/Executive Interview: May involve a final discussion with other company leaders.

Portfolio Review Tips:

• Tell a Story: Structure your case studies to clearly articulate the problem, your role, the design process, key decisions, user insights, and quantifiable outcomes.
• Show, Don't Just Tell: Use visuals, prototypes, and data to demonstrate your design thinking and impact.
• Highlight Leadership & Process: Since this is a leadership role, showcase how you've influenced design strategy, built teams, or improved processes. Demonstrate your ability to set standards and mentor others.
• Focus on Impact: Quantify the results of your design work whenever possible (e.g., increased conversion rates, improved user satisfaction, reduced churn).
• Tailor to Jerry.ai: Research Jerry.ai's products and mission. Be prepared to discuss how your skills and experience align with their goals and challenges. Show enthusiasm for their "super app" vision.

Challenge Preparation:

• Understand the Domain: Familiarize yourself with the InsurTech, FinTech, and consumer ownership spaces. Think about common user pain points and potential solutions.
• Problem-Solving Approach: Be ready to articulate your approach to solving ambiguous design problems. How do you gather information, define the problem, brainstorm solutions, and test them?
• System Thinking: Be prepared to discuss how you would approach building or evolving a design system for a rapidly growing consumer app.
• Collaboration Scenarios: Think about how you would handle disagreements or differing opinions with product or engineering teams.

📝 Enhancement Note: The emphasis on "0 to 1" and building a team suggests the interview process will heavily scrutinize leadership potential, strategic thinking, and the ability to create structure and process. Demonstrating experience in similar "build" scenarios will be crucial.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (explicitly mentioned, essential), Sketch, Adobe Creative Suite (as supporting tools).
• Prototyping Tools: InVision, ProtoPie, Framer (familiarity with advanced prototyping is beneficial).
• User Research & Testing: UserTesting.com, Lookback, Maze, Hotjar, Google Analytics, Mixpanel, Amplitude.
• Collaboration & Project Management: Slack, Asana, Jira, Confluence, Miro, Notion.

Analytics & Reporting:

• Product Analytics: Mixpanel, Amplitude, Google Analytics, Tableau (for dashboarding insights).
• Data Visualization: Tableau, Looker, Power BI (for presenting data-driven insights).
• A/B Testing Platforms: Optimizely, VWO, Google Optimize.

CRM & Automation:

• CRM: Salesforce, HubSpot (understanding CRM principles and data flow is helpful for user segmentation and personalization).
• Automation: Zapier, Make (formerly Integromat) (for understanding workflow automation, though less directly for design, it shows an appreciation for efficiency).
• Integration: Understanding API concepts and how different systems connect.

📝 Enhancement Note: Proficiency in Figma is explicitly required. A strong understanding of product analytics tools (Mixpanel, Amplitude) and user research platforms is critical for a data-informed design leader. Familiarity with building and managing design systems is also a key technical requirement.

👥 Team Culture & Values

Operations Values:

• User-Centricity: A deep commitment to understanding and serving the user, making complex financial and ownership tasks simpler and less stressful.
• Speed & Agility: A culture that values rapid iteration, quick decision-making, and the ability to move fast in a competitive market.
• Thoughtfulness & Craftsmanship: While moving fast, there's an equal emphasis on delivering high-quality, well-executed design solutions.
• Collaboration & Egoless Approach: Working together effectively across disciplines, with a focus on team success over individual accolades.
• Mission-Driven: A shared passion for the company's mission to empower everyday Americans with control over their major assets.
• Curiosity & Learning: Encouraging a mindset of continuous learning, exploration, and embracing new challenges.

Collaboration Style:

• Cross-Functional Integration: Expect close collaboration with Product Management, Engineering, and Data teams, requiring strong communication and partnership skills.
• Feedback-Rich Environment: A culture that encourages providing and receiving constructive feedback to drive continuous improvement in design and product.
• Shared Ownership: A belief that design is a shared responsibility, with all team members contributing to product excellence.
• Data-Informed Discussions: Decisions and discussions are expected to be backed by user research, data, and clear reasoning.

📝 Enhancement Note: The "egoless" characteristic is important for a leader who needs to build consensus and foster a collaborative environment, especially in a "0 to 1" team-building scenario.

⚡ Challenges & Growth Opportunities

Challenges:

• Building a Design Function: Establishing design processes, standards, and a team culture from the ground up in a fast-paced environment requires strong organizational and leadership skills.
• Balancing Strategy & Execution: As a hands-on leader, balancing strategic vision with the day-to-day demands of individual design contributions can be challenging.
• Cross-Functional Alignment: Ensuring consistent design vision and execution across multiple product areas and collaborating effectively with diverse teams.
• Scaling Processes: Developing design processes that are scalable and adaptable as the company and design team grow.
• Navigating Ambiguity: Operating in a "0 to 1" environment means dealing with evolving priorities and undefined areas, requiring adaptability and resilience.

Learning & Development Opportunities:

• Foundational Leadership: The opportunity to define and build a design organization from its inception provides unparalleled leadership development.
• Strategic Impact: Direct influence on a product that aims to disrupt massive markets offers significant learning in business strategy and market dynamics.
• Mentorship & Team Building: Developing skills in hiring, coaching, and growing a design team.
• Industry Exposure: Gaining expertise in the complex InsurTech, FinTech, and consumer ownership spaces.
• Continuous Learning: Engaging with new technologies, design methodologies, and market trends in a dynamic startup environment.

📝 Enhancement Note: The primary challenge is the "build" aspect of the role – creating the function, team, and processes. Success here will lead to significant leadership growth and strategic impact.

💡 Interview Preparation

Strategy Questions:

• Design Vision & Leadership: "Describe your philosophy on leading design teams and establishing design culture in a high-growth startup. How would you approach building Jerry.ai's design function from the ground up?" (Prepare examples of how you've set vision, hired, mentored, and established processes.)
• Process & Collaboration: "How do you ensure effective collaboration between design, product, and engineering? Describe a time you had to navigate a significant disagreement with a cross-functional partner and how you resolved it." (Focus on communication, data-driven arguments, and consensus-building.)
• Problem-Solving & Impact: "Walk us through a challenging product design problem you solved. What was your process, what were the key trade-offs, and what was the measurable impact of your solution?" (Use a STAR method approach, highlighting your role, actions, and results.)

Company & Culture Questions:

• Mission Alignment: "Why are you drawn to Jerry.ai's mission to simplify car and home ownership? How does this resonate with your career goals?" (Show genuine interest and understanding of the problem Jerry is solving.)
• Startup Environment: "How do you thrive in ambiguous or '0 to 1' environments? What are your expectations for working in a fast-paced startup?" (Highlight adaptability, proactivity, and comfort with uncertainty.)
• Design Team Dynamics: "What qualities do you look for when hiring designers? How do you foster a supportive and high-performing design team environment?" (Demonstrate your approach to team building and talent development.)

Portfolio Presentation Strategy:

• Narrative Structure: Frame each case study as a story with a clear beginning (problem), middle (process, decisions, challenges), and end (solution, impact, learnings).
• Highlight Your Role: Clearly articulate your specific contributions, especially in leadership and strategic decision-making, beyond just UI execution.
• Data & Metrics: Integrate data points and user feedback throughout your presentation to support your design decisions and demonstrate impact. Show how you measure success.
• System Thinking: If applicable, dedicate a portion to showcasing your understanding of design systems, component libraries, and scalability.
• Conciseness & Clarity: Be mindful of time. Present your strongest work clearly and be prepared to dive deeper into specific areas based on interviewer questions.

📝 Enhancement Note: The interview will likely probe deeply into your ability to build and lead, not just design. Be prepared to discuss your experience in process creation, team development, and strategic contribution in addition to your design craft.

📌 Application Steps

To apply for this Head of Design position:

• Submit your application through the provided link on Ashbyhq.
• Portfolio Customization: Curate your portfolio to prominently feature 3-5 strong case studies that highlight end-to-end product design ownership, leadership experience, and quantifiable impact. Ensure these examples demonstrate your ability to work with consumer products and in fast-paced environments.
• Resume Optimization: Tailor your resume to emphasize leadership experience, team building, process establishment, and specific achievements in product design. Use keywords such as "design leadership," "product strategy," "user experience," "Figma," "design systems," and "cross-functional collaboration." Quantify your achievements wherever possible.
• Interview Preparation: Practice articulating your design philosophy, leadership approach, and problem-solving methodologies. Prepare to discuss your experience in shaping design teams and processes. Rehearse your portfolio walkthrough, focusing on storytelling and impact.
• Company Research: Thoroughly research Jerry.ai's mission, products, and recent news. Understand their "super app" strategy for car and home ownership and be prepared to discuss how your design vision aligns with their goals. Familiarize yourself with their competitors and the InsurTech/FinTech landscape.

⚠️ 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.