
Job Overview
Location
Toronto, Ontario
Job Type
Full-time
Category
HR & Recruiting
Date Posted
May 12, 2026
Full Job Description
📋 Description
- • As a Legal Researcher at Jerry.ai, you will play a critical role in supporting the company’s legal and compliance functions by owning corporate governance, conducting applied legal research, and driving resolution of complex regulatory and consumer issues.
- • Day to day, you will manage entity compliance across U.S. and Canada jurisdictions, conduct structured legal research on regulatory and product-related matters, lead responses to consumer escalations and regulatory inquiries, collaborate with Product and Engineering teams on compliance reviews, monitor IP risks, lead compliance audits, and build scalable legal workflows using automation and AI tools.
- • Jerry.ai is a high-growth, venture-backed startup recognized as a Forbes Top Startup Employer, with over $240M in funding and 60X revenue growth in six years, operating at the intersection of law, business, and technology to revolutionize car ownership through its AI-powered super app.
- • In this role, you will gain hands-on legal experience in a fast-paced, meritocratic environment, develop end-to-end ownership of meaningful legal workstreams, build expertise in compliance and regulatory affairs, and accelerate your legal career by working directly with executive leadership and cross-functional teams from elite backgrounds.
🎯 Requirements
- • Strong academic background in law (Bachelor’s, JD, LLM, or PhD in a legal field)
- • Proven resourcefulness and initiative — ability to find answers independently and close loops without prompting
- • Interest in leveraging AI, technology, or automation to optimize legal workflows and reduce manual work
- • Impeccable attention to detail with a zero-error mindset in regulatory filings, compliance audits, and deadline management
- • Comfort operating in high-performance, ambiguous environments with urgency and full ownership of outcomes
🏖️ Benefits
- • Comprehensive benefits package including health, dental, and vision coverage
- • Paid time off and paid parental leave
- • 401(K) plan with employer matching
- • Wellness benefits and equity opportunities as part of total rewards
- • Opportunity to work remotely with optional onsite access to offices in Palo Alto, Toronto, and New York
Skills & Technologies
About Jerry Technologies Inc.
Jerry Technologies offers a mobile-first AI platform that automatically compares insurance quotes, refinances auto loans, and shops for home and renters coverage. Users submit photos of existing policies, and the app retrieves and compares rates from carriers to find lower premiums or better terms. The company earns commissions from insurers when policies are switched or originated through its platform, serving consumers seeking to reduce recurring auto and home expenses without manual comparison shopping.
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