Head of Design

Jerry; Toronto; Remote; CAD 120,000 - 150,000; Full time

Job summary

A forward-thinking tech company in Toronto is seeking a Head of Design to shape the future of car and home ownership products. You will lead a small design team and work closely with founders to drive design excellence across platforms. The ideal candidate is a hands-on leader with strong visual design skills, and experience in building user-centric products. This role offers competitive salary and fully remote work options.

Benefits

Competitive salary and stock options

Fully remote work flexibility

Comprehensive benefits

Qualifications

• Hands-on design leader who loves to design
• Exceptional visual and interaction design skills
• Experience in high-growth environments

Responsibilities

• Lead design of product features from discovery to delivery
• Set design excellence standards and build design culture
• Hire, mentor, and manage a design team over time
• Evolve visual design system across platforms

Skills

Visual design skills

Interaction design skills

Leadership

Figma proficiency

Strategic thinking

Job description

Join to apply for the Head of Design role at Jerry

Join to apply for the Head of Design role at Jerry

Get AI-powered advice on this job and more exclusive features.

You could lead design anywhere. Why join 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).

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 due to a disability, please contact us at [e-mail]

About Jerry.ai

Jerry.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets.

Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all.

We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started.

Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing.

Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.

Seniority level

Seniority level

Executive

Employment type

Employment type

Full-time

Job function

Job function

Design, Art / Creative, and Information Technology

Industries

Software Development

Referrals increase your chances of interviewing at Jerry by 2x

Sign in to set job alerts for “Head of Design” roles.

Director of Product Design and Research (Contract)

Global Director for Building Service Line & Sustainability

Greater Toronto Area, Canada 2 months ago

Engineering Manager - Public Cloud, Python, Golang

Engineering Manager - Public Cloud, Python, Golang

Engineering Manager, Frontend (Remote - Canada)

We’re unlocking community knowledge in a new way. Experts add insights directly into each article, started with the help of AI.

J-18808-Ljbffr