Job Overview
Location
Toronto, Ontario
Job Type
Full-time
Category
Product Marketing Manager
Date Posted
April 7, 2026
Full Job Description
đź“‹ Description
- • As a Legal Researcher at Jerry.ai, you will play a critical role in ensuring corporate compliance and mitigating legal risk across U.S. and Canadian jurisdictions, directly supporting the company’s rapid growth and innovation in the insurtech space.
- • You will work closely with Legal Counsel and executive leadership, translating complex legal and regulatory requirements into practical, scalable business solutions that impact product development, operations, and brand protection.
- • This role is ideal for ambitious law graduates seeking to build a high-impact legal career in a fast-paced, meritocratic startup environment where performance drives advancement and ownership is expected from day one.
- • You will own end-to-end legal workstreams, including corporate compliance, regulatory research, consumer issue resolution, IP protection, and compliance audits, while designing tech-enabled systems to improve legal efficiency.
- • Day-to-day responsibilities include managing entity compliance across jurisdictions, conducting structured legal research on regulatory and consumer protection matters, and synthesizing findings into actionable recommendations for stakeholders.
- • You will serve as a first-line responder to complex consumer escalations and regulatory inquiries, investigating root causes, assessing legal exposure, and leading compliance training initiatives to strengthen organizational awareness.
- • Collaboration with Product, Engineering, and Operations teams will be central to reviewing features, user flows, and policies for legal adherence, ensuring compliance is built into the product lifecycle.
- • You will monitor potential intellectual property infringements and support enforcement efforts, including drafting cease-and-desist notices and contributing to brand protection strategies.
- • Leading compliance audits across operations, you will proactively identify risks, ensure adherence to evolving regulations, and drive continuous improvement to exceed industry benchmarks.
- • A key part of the role involves identifying repetitive legal tasks and designing scalable solutions using AI, automation, or low-code tools to modernize the legal function.
- • You will be expected to exercise independent judgment, navigate legal ambiguity with urgency, and maintain a zero-error mindset in all regulatory filings, deadlines, and cross-functional projects.
- • The role offers hands-on experience at the intersection of law, business, and technology, allowing you to grow your legal expertise while contributing to a mission-driven company simplifying car ownership for millions.
- • You will join a high-performing team of professionals from top-tier companies like Nvidia, Amazon, McKinsey, and Bain, working in a culture that values resourcefulness, curiosity, and egoless collaboration.
- • Jerry.ai’s commitment to innovation and excellence is reflected in its #1 app store ranking, 4.7-star rating, and over 5 million customers, providing a dynamic environment where your work has measurable impact.
🎯 Requirements
- • Strong academic background in law, including a Bachelor’s degree, JD, LLM, or PhD in a legal field.
- • Proven resourcefulness and a driver mindset — demonstrated ability to find answers proactively and close loops without prompting.
- • Exceptional attention to detail with a zero-error approach to regulatory filings, compliance audits, and deadline management.
- • Interest in leveraging AI, technology, or automation to optimize legal workflows and improve efficiency.
- • Comfort operating in high-ambiguity, high-urgency environments with a strong sense of ownership and accountability.
🏖️ Benefits
- • Comprehensive health, dental, and vision coverage for regular employees.
- • Paid time off, paid parental leave, and access to a 401(K) plan with employer matching.
- • Wellness benefits and opportunities for equity grants as part of the total rewards package.
- • Flexibility to work fully remote with optional onsite access to offices in Toronto, Palo Alto, or New York.
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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