Job Overview
Location
Toronto, Ontario
Job Type
Full-time
Category
HR & Recruiting
Date Posted
May 4, 2026
Full Job Description
đź“‹ Description
- • As a Legal Researcher at Jerry.ai, you will play a critical role in ensuring legal and regulatory compliance across U.S. and Canada jurisdictions while supporting high-impact business decisions in a fast-growing startup environment.
- • You will own corporate compliance and governance, lead legal research and applied analysis, drive resolution of complex consumer and regulatory issues, partner cross-functionally on product and compliance matters, strengthen IP protection, run compliance audits, and build scalable legal systems using AI and automation tools.
- • Jerry.ai is a Forbes Top Startup Employer with $240M in funding and 60X revenue growth in six years, operating as America’s first and only super app for car ownership, backed by AI and machine learning, with over 5 million customers and offices in Palo Alto, Toronto, and New York.
- • You will gain hands-on legal experience, exercise independent judgment, translate legal ambiguity into practical decisions, and accelerate your career in a meritocratic, high-performance environment that values ownership, resourcefulness, and tech-enabled solutions.
🎯 Requirements
- • Academic excellence in law (Bachelor’s, JD, LLM, or PhD in a legal field)
- • Proven track record of extreme resourcefulness and ownership of outcomes
- • Interest in using AI/technology to optimize legal workflows and processes
- • Impeccable attention to detail with a zero-error mindset in regulatory filings and compliance audits
- • Ability to thrive in ambiguous, high-urgency environments with strong organizational rigor
🏖️ Benefits
- • Comprehensive health, dental, and vision coverage
- • Paid time off and paid parental leave
- • 401(K) plan with employer matching
- • Wellness benefits and equity opportunities
- • Opportunity to work remotely with optional onsite access in Toronto, Palo Alto, or New York
Skills & Technologies
About Jerry Technologies, Inc.
Jerry is a technology company focused on simplifying and personalizing the car ownership experience. They offer a mobile app that acts as a digital assistant for car owners, providing services such as insurance comparison and purchasing, maintenance scheduling, roadside assistance, and parking assistance. Jerry aims to reduce the stress and cost associated with owning a vehicle by leveraging AI and data analytics to offer tailored solutions and competitive pricing. Their platform connects users with a network of service providers and insurance carriers, streamlining the entire car ownership lifecycle.
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