Legal Researcher (Remote) at Jerry.ai in Toronto, Ontario, Canada

You could work anywhere. Why http://jerry.aiJerry.ai http://Jerry.ai? - Join a Forbes Top Startup Employer with $240M in funding and 60X revenue growth in 6 years. - Partner closely with our Legal Counsel and team mates from companies like Nvidia, Amazon, McKinsey, Bain, BCG, etc. - Thrive in a true meritocracy - we promote based on performance, not tenure. - Gain hands-on legal experience and accelerate your growth within a high-performing company. About the opportunity: Are you an ambitious, aspiring legal professional looking to accelerate your career in-house at a high growth startup? As a Legal Researcher at Jerry.ai http://Jerry.ai, you’ll be embedded in the business from day one, working closely with our Legal Counsel, and collaborating directly with our executive leadership team. This role is designed for high-performing law graduates who want to build a rigorous, high-impact legal career outside the traditional law firm path. This is not a task-based or purely research role. You will be expected to exercise independent judgment, translate legal ambiguity into practical decisions, and take end-to-end ownership of meaningful workstreams. If you’re resourceful, driven, and excited about building a foundation for a high-impact legal career at the intersection of law, business, and technology, we’d love to hear from you! This is a fully remote full-time role with options to work onsite (we have offices in Palo Alto, Toronto, and New York). What you’ll do: - Own Corporate Compliance & Governance: Manage entity compliance across U.S. and Canada jurisdictions. You’ll identify risks proactively and implement systems to prevent lapses – not just react to deadlines. - Lead Legal Research & Applied Analysis: Conduct structured legal research on regulatory, consumer protection, and product-related issues. Synthesize findings into clear, actionable recommendations for business stakeholders – not just memos. - Drive Resolution of Complex Issues: Serve as a first-line owner for nuanced consumer escalations and regulatory inquiries. Investigate root cause, assess legal exposure, propose practical and scalable solutions, and spearhead compliance training initiatives that elevate our entire work force. - Partner Cross-functionally on Product & Compliance: Work closely with Product, Engineering, and Operations to review features, flows, and policies for legal and regulatory compliance. Help translate legal requirements into operational and product decisions. - Strengthen IP and Protect the Brand: Monitor potential infringements and support enforcement strategies, including drafting and initiating cease-and-desist workflows. - Run Tight Audits: Lead our compliance audits across operations. You’ll proactively monitor key risk areas, ensuring our practices don’t just meet baseline regulatory standards, but set the industry benchmark for excellence. - Build Systems, Not Just Outputs: Identify repetitive or manual legal work and design scalable solutions using AI and low-code tools, automation, or process improvements. Contribute to building a legal function that is efficient, tech-enabled, and forward-looking. Ideal profile: - Academic Excellence: Strong background in law, whether through a Bachelor’s degree, JD, LLM, or PhD in a legal field. - Driver Mindset: A proven track record of extreme resourcefulness. You are the type of person who finds the answer before asking the question. You have an innate need to close loops. - Product & Tech Savvy: You have an interest in using AI/technology to optimize workflows. You prefer a spreadsheet or an automated tool over a manual checklist. - Impeccable Attention to Detail: You have a "zero-error" mentality when it comes to regulatory filings and compliance audits. You have the organizational rigor to ensure no deadline or cross-functional project ever slips through the cracks. - Thrive in High-Performance Environments: You’re comfortable with ambiguity and operate with a deep sense of urgency. You take full ownership of your output. While we appreciate your interest and application, only applicants under consideration will be contacted. 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 recruiting@jerry.ai recruiting@getjerry.com 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.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets. Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all. We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started. Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing. Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.