Operations Associate (Legal & Compliance) 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.
Jerry operates across the US and Canada, and our legal team keeps all of it running: entity filings, IP protection, product reviews, consumer escalations, and audits. The team is small, so this role comes with real scope early. You’ll run core legal operations and rebuild them with AI and low-code tools, so a small team can do the work of a much larger one.
The person who succeeds in this role is a natural driver: someone who owns a project from start to finish, solves complex problems without a manual, and has the grit to thrive in a startup environment. If you are eager to sit at the intersection of law, technology, and AI-driven efficiency, we want to hear from you.
Why You Will (Or Won’t) Like Working Here
Real ownership early:
You report directly to our Legal Counsel and work closely with them across the team’s full scope. The projects you take on are yours from start to finish.
Room to build:
Many of our legal processes are still being optimized. You’ll decide how they should work and build the systems behind them.
Building and operating:
Alongside the building, a large share of the job is recurring work: filings, deadlines, and audits that have to be done exactly right, every time. Your accuracy keeps Jerry in good standing in every jurisdiction, and people who enjoy both sides of the role do well here.
Growth that tracks results:
You’ll learn from leaders who come from Amazon, Better, LinkedIn, McKinsey, BCG, and Bain. Promotion is based on performance and ownership alone, so strong work moves you forward fast.
What You’ll Own
Automation:
Use AI and low-code tools to replace manual legal tasks with workflows that run on their own.
Legal and regulatory projects:
Work with our Legal Counsel on legal research, contract reviews, and other substantive projects as new questions come up.
Entity compliance:
Keep Jerry’s corporate entities in good standing across the US and Canada, handling annual reports and state requests end to end on your own.
Brand protection:
Monitor Jerry’s intellectual property, find infringements, and initiate cease-and-desist workflows.
Consumer escalations:
Investigate complex escalations to their root cause, recommend fixes, and turn recurring issues into compliance training for teams across the company.
Product compliance reviews:
Review products and processes for compliance risk and user friction, then work with Engineering and Product to fix the underlying issue.
Compliance audits:
Lead audits across operations and keep watch on the highest-risk areas between them.
Who You Are
A Closer:
You track every open item until it’s done, and you find the answer yourself before asking someone else for it.
A Builder:
The second time you do a task by hand, you start working out how to automate the third. You reach for a spreadsheet or a low-code tool before a manual checklist.
A Zero-Error Operator:
Regulatory filings and audits leave no room for mistakes, and you work accordingly. You keep your own system so no deadline or cross-functional project slips.
A Proactive Communicator:
You provide updates without being chased, flag blockers early, and make sure teammates know what happens next.
Comfortable with ambiguity:
You can take an unclear brief, define the problem yourself, and move on it with urgency.
What You’ll Bring
A Bachelor’s degree from an academically rigorous program, with a record of high performance.
A track record of owning projects start to finish and solving problems without being told how, at school, at work, or on your own.
Demonstrated interest in using AI and technology to improve how work gets done, such as a tool, automation, or process you built yourself.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.
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.Ai
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 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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