Jerry is building the first AI-powered advisor to manage all your physical assets. Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive. Imagine having a trusted friend in your pocket who takes care of everything: they find you…
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Building the first AI-powered advisor to manage all your physical assets.
Jerry is building the first AI-powered advisor to manage all your physical assets. Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive. Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry. We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and have been profitable since 2024. We're now expanding into home, motorcycle, RV, and beyond. Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft. We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership. We are a remote-first company, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto. Visit jerry.ai/careers/ for more information.
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Jerry.ai has 10 open jobs in Canada as of November 6, 2026. Top locations: Toronto.
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Jerry.ai
2+ YOECandidates need a JD or LLM with strong academic results and admission to practice in a U.S. state or Ontario in good standing. They need 2+ years of legal experience, including commercial agreement work, and strong research and writing skills.
AI and automation research and drafting tools
Jerry.ai
4+ YOECandidates need 4+ years of finance experience, ideally including investment banking or private equity and strategic finance at a high-growth company. They need a quantitative degree, strong financial modeling skills, unit economics knowledge, and the ability to write clear narratives for executives.
NetSuite, Ramp
Jerry.ai
4+ YOECandidates need 4+ years of experience, ideally including time at an investment bank, corporate development group or private equity firm and in strategic finance or FP&A at a high-growth company. They need a quantitative bachelor's degree, strong financial modeling skills, unit economics experience in consumer or marketplace businesses, and fluency with AI tools.
NetSuite, Ramp
Jerry.ai
4+ YOECandidates need 4+ years of finance experience, ideally including investment banking, corporate development or private equity plus strategic finance or FP&A at a high-growth company. They need strong financial modeling skills, unit economics knowledge (CAC, LTV, payback) and the ability to explain numbers clearly to executives.
NetSuite, Ramp
Jerry.ai
2+ YOECandidates need a bachelor's degree in any discipline and at least 2 years of hands-on HR generalist experience, including drafting policies and running payroll and compliance filings. In-house multi-state compliance experience and comfort with AI-driven process change are also required.
Regulatory compliance, Payroll, Operations management, Compensation and benefits
Jerry.ai
2+ YOECandidates need a bachelor's degree and at least 2 years of hands-on HR generalist experience, including in-house multi-state compliance work. They must be comfortable in a small team handling payroll, benefits and compliance, and open to building with AI.
Jerry.ai
Candidates need a Bachelor's degree, a track record of owning projects independently, and hands-on experience using AI and technology to improve work. Compliance, legal operations or audit experience is a plus but not required.
AI tools, low-code tools
Jerry.ai
Candidates need a Bachelor's degree from a strong academic program and a record of owning projects from start to finish. Jerry.ai also wants someone who has built or improved work with AI, automation or technology.
AI tools, low-code tools
Jerry.ai
Candidates need a JD or LLM with strong academic results, experience drafting or reviewing contracts, and strong legal research and writing skills. Strong organization and the ability to manage several matters and deadlines at once are also required.
Negotiate settlements, Research, Regulatory compliance, Legal research, Project management, Compensation and benefits
Jerry.ai
6+ YOECandidates need 6+ years in venture capital, private equity, or hands-on operating roles in fast-growing startups, plus a bachelor's degree in any discipline. They must be able to work in person in the Palo Alto office.
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