Legal Researcher (Remote) Toronto, Ontario

More than 80% of Americans own a car and see it as a fundamental necessity, yet the experience of owning one is stuck in the 90s. At Jerry.Ai, we are building the first app to manage it all. Since launching in 2019, we’ve reached 5M+ customers, raised $240M+, scaled revenue 70X, and achieved profitability in 2024.
Operating across the US and Canada brings a steady flow of regulatory, consumer protection, and product questions that need clear legal answers fast. As our Legal Researcher, you’ll work closely with our Legal Counsel and partner with teams across Jerry to research hard questions and turn your findings into decisions the business can act on.
This role is built for high-performing law graduates who want a rigorous in-house legal career outside the law firm path. It’s highly hands-on: you’ll draft and negotiate agreements with partners and vendors, research licensing and regulatory requirements, support product and compliance reviews, and help solve new legal questions as the business grows. If you succeed, Jerry’s leaders make faster, better-informed decisions on legal risk, and you’ll have owned work that shapes how the company grows.
Why You Will (Or Won’t) Like Working Here
A seat close to the decisions:
Your work will help inform important business decisions, and you’ll have opportunities to present your analysis and recommendations to Legal and business leaders. You’ll need to be comfortable developing a point of view, explaining your reasoning, and incorporating feedback.
Judgement that grows with experience:
Many of the questions you’ll take on have no clear precedent. You’ll dig into the facts and law, develop a thoughtful recommendation, and bring a clear point of view for discussion and review.
An in-house path from the start:
You’ll learn how legal work drives business decisions without spending years at a firm first. There’s no large-firm training program here. You’ll learn by doing real work, and the faster you pick things up and take initiative, the more responsibility you’ll earn.
Growth that tracks results:
You’ll work with teammates from companies like Nvidia, Amazon, McKinsey, Bain, and BCG. Promotion is based on performance alone, so strong work moves you forward fast.
What You’ll Own
Contracts:
Draft and review agreements with partners and vendors, identify key issues, and support negotiations through execution.
Legal research and recommendation:
Research federal and state regulatory, consumer protection, insurance, privacy, and other legal questions, and turn your findings into clear, practical recommendations business leaders can act on.
Licensing and regulatory compliance:
Support the licenses and recurring regulatory requirements needed for Jerry’s products and operations, and help build systems that keep them current.
Product review:
Review features, flows, and processes with Product, Engineering, and Operations, and support translating legal requirements into product decisions.
Escalations and regulatory inquiries:
Investigate complex consumer escalations and regulatory inquiries, identify root causes and potential legal issues, propose scalable fixes, and turn recurring issues into company-wide compliance training.
Policies, procedures, and compliance systems:
Help design and improve Jerry’s legal and compliance policies, procedures, and operational controls to manage legal and business risk.
Emerging legal issues : Take on new legal and regulatory questions as Jerry launches products, enters partnerships, and expands its business.
Who You Are
A Practical Analyst:
You can read a regulation, work out what it means for a product decision, and explain it clearly and concisely.
A Closer:
You find the answer yourself before asking for it, and you track every open item until it’s resolved.
A Builder:
When you see the same manual task twice, you start looking for a way to automate it.
A Zero-Error Operator:
You review every contract and filing with total precision and keep your own system so no deadline slips.
A Proactive Communicator:
You keep people updated without being chased, flag blockers early, and make sure teammates know what happens next.
Hands-on and Unpretentious:
You’re as ready to clean up a tracker or follow up on an overdue item as you are to dig into a difficult legal question.
What You’ll Bring
A JD or LLM, with a record of high academic performance.
Experience drafting or reviewing contracts, through coursework, a clinic, an internship, or work.
Strong legal research and writing skills, with the ability to turn complex analysis into clear, practical recommendations.
Strong organization and project-management skills, with the ability to manage multiple matters and deadlines at once.
Please note: Jerry.Ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.
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 View email address on ca.hrm.tc.
The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.
We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.
About Jerry.AiJerry 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 achieved profitability in 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 support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.
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