Jerry

Head of Design

San Francisco, California, United States

Not SpecifiedCompensation
Expert & Leadership (9+ years)Experience Level
Full TimeJob Type
UnknownVisa
Fintech, Insurtech, Real EstateIndustries

About Jerry.ai

Your car and your home are the two most expensive things you’ll ever own — and the hardest to manage. At Jerry, we’re building the first super app to help everyday Americans take control of both. From insurance and financing to repairs and real estate, we’re reimagining what it means to own and maintain your car and home. This is a $5 trillion+ problem — and we’re the only company tackling it end to end.

Join us as our Head of Design. Come shape the future of car and home ownership, and build a world-class design team from the ground up. You’ll work directly with our Cofounder & Head of Product, lead by example through hands-on design work, and hire the small but mighty, high-craft team that will bring our next generation of products to life — helping us serve our next 50 million users.

How You’ll Make an Impact

  • Work on a mission that matters: Help the bottom 90% of Americans reduce financial stress and gain control over their most important assets.
  • Build from 0 to 1: Our design team is still small (currently 2 designers), giving you direct access to founders and leaders, and ownership to shape our product and process.
  • Massive market, once-in-a-generation opportunity: The car and home ownership space are $2T and $3T markets, respectively. Jerry is the only startup building a unified platform to serve both.
  • Accelerate our trajectory: 5M+ customers, $240M raised, and 60X revenue growth in 6 years so far. Help us become a $10B consumer company by 2030.

What You’ll Own

  • Lead the design of product features across our entire mobile and web surface from discovery to delivery — flows, wireframes, prototypes, UI, and iteration
  • Set the bar for design excellence through your own craft while building a strong design culture around speed, thoughtfulness, and usability
  • Partner closely with product, engineering, and data to explore opportunities, test hypotheses, and ship fast
  • Leverage user research and behavioral data to refine and improve experiences post-launch
  • Evolve our visual design system and component libraries across mobile and web platforms
  • Hire, mentor, and manage a small but high-performing design team over time, and elevate design quality across the company through mentorship, feedback, and high standards
  • Establish scalable design processes, tools, and rituals as we grow the team

Who You Are

  • You’re a hands-on design leader who still loves to design
  • You have exceptional visual and interaction design skills and set a high bar for quality
  • You’ve led design for consumer-facing products, ideally in high-growth or fast-paced environments
  • You can zoom out to think strategically but are equally comfortable executing
  • You lead with curiosity, empathy, and clarity — and know how to hire and develop great designers
  • You’re confident navigating ambiguity and energized by 0→1 opportunities
  • You’re fluent in Figma and familiar with multi-platform systems (iOS, Android, Web)

Compensation & Perks

  • Competitive salary and stock options, flexible cash vs equity structure based on your circumstances and preference.
  • Fully remote work with hubs in San Francisco, New York, Toronto, Palo Alto (in-office optional).
  • Comprehensive benefits (401K match, health, dental, vision, mental health support, etc).

Additional Information

While we appreciate your interest and application, only applicants under consideration will be contacted.

Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws. Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation...

Skills

Product Design
Mobile Design
Web Design
UI Design
UX Design
Prototyping
Wireframing
Design Leadership
Team Building
Cross-functional Collaboration

Jerry

Digital platform for car insurance and services

About Jerry

Jerry is a digital platform that helps car owners manage their expenses by providing a mobile app called AllCar™. This app allows users to compare insurance policies, refinance car loans, and monitor repair costs, while also rewarding good driving habits. Jerry stands out from competitors by offering a user-friendly experience that can lead to significant savings, with some users reporting reductions in insurance payments of up to $300 per month. The company's goal is to simplify car ownership by providing a comprehensive solution for insurance, financing, and maintenance.

Palo Alto, CaliforniaHeadquarters
2017Year Founded
$222.8MTotal Funding
DEBTCompany Stage
Automotive & Transportation, Consumer Software, FintechIndustries
201-500Employees

Benefits

401K / Retirement Plan
Performance Bonus
Dental Insurance
Health & Wellness Package
Paid Time Off

Risks

Data privacy scrutiny may challenge Jerry's operations and regulatory compliance.
Rising pedestrian accidents could increase insurance premiums, affecting competitive rates.
New features like GarageGuard require significant investment, straining financial resources.

Differentiation

Jerry offers a comprehensive app for car insurance, loans, and maintenance.
The AllCar™ App rewards users for safe driving habits, enhancing user engagement.
Jerry simplifies car ownership with a seamless process for switching insurance providers.

Upsides

Recent $110M funding boosts Jerry's service expansion and tech infrastructure.
AI integration in insurance comparison enhances personalized offerings and customer satisfaction.
GarageGuard and DriveShield features attract users with comprehensive car management solutions.

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