Associate Counsel (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 U.S. and Canada brings a steady flow of commercial, regulatory, consumer protection, and product questions. As our Associate Counsel, you’ll report directly to our Legal Counsel and work with teams across Jerry to turn complex legal issues into practical that help the business move forward.This role is designed for a lawyer with law firm and/or in-house experience who wants broad responsibility in a growing technology company. You’ll draft and negotiate agreements, advise on product and compliance questions, and drive assigned matters from initial assessment through resolution. You’ll develop your own recommendations and manage day-to-day execution, bringing significant decisions and novel or higher-risk issues to our Legal Counsel.Why You Will (Or Won’t) Like Working Here
Substantive ownership:
You’ll manage matters, work directly with business partners, and bring a clear point of view. You’ll need to distinguish the issues that matter from those that can be resolved pragmatically.
Broad exposure:
Your work will span contracts, product launches, insurance and consumer regulation, privacy, and disputes. You don’t need to arrive as an expert in every area, but you should enjoy learning unfamiliar subjects and applying sound judgment.
A small team with a hands-on approach:
Our legal team is two people today. You’ll work closely with our cofounder and executives on legal issues that shape business decisions, organize your own matters, follow through on implementation, and help with operational details when needed.
Technology as part of the work:
We use AI and automation to improve research, drafting, and legal processes. You’ll be expected to use these tools thoughtfully, verify their output, and take responsibility for the quality of your work.
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
Commercial agreements:
Draft, review, and negotiate agreements with carriers, business partners, and vendors. Identify material risks, propose practical terms, and manage negotiations and internal coordination through execution.
Product and regulatory advice:
Research federal and state insurance, consumer protection, privacy, and other requirements. Translate your analysis into clear recommendations on new products, customer flows, disclosures, consent, marketing, and operational processes.
Consumer escalations and regulatory matters:
Investigate complex complaints and regulatory inquiries, identify relevant facts and legal issues, and prepare proposed responses. Work with Legal and business teams to resolve matters and address recurring causes.
Compliance and risk management:
Help design policies, procedures, training, and controls. Review audit findings, identify issues requiring legal judgment, and work with operational owners to implement and track corrective actions.
Licensing and corporate matters:
Address substantive questions arising from entity maintenance, licensing, appointments, and business expansion. Work with colleagues handling recurring compliance operations and elevate material risks.
Emerging issues and legal processes:
Take on new legal questions as Jerry launches products and enters partnerships. Improve templates, guidance, and workflows so the team can deliver consistent advice efficiently.
Who You Are
Practical and Thoughtful:
You develop a recommendation, explain your reasoning clearly, and balance legal risk with business objectives.
An Accountable Owner:
You keep matters moving, manage deadlines, and follow issues through implementation. You investigate independently and recognize when to seek input or elevate.
A Clear Communicator:
You write concisely, give useful status updates without being chased, flag blockers early, and make the next step clear.
A Zero-Error Operator:
You review every contract and filing with total precision, down to defined terms, dates, and cross-references.
What You’ll Bring
A JD or LLM, with a record of high academic performance.
Admission to practice in at least one U.S. state or in Ontario, in good standing.
2+ years of relevant legal experience at a law firm and/or in-house, including substantive experience drafting, reviewing, or negotiating commercial agreements.
Strong legal research, analysis, and writing skills, with the ability to develop practical recommendations on unfamiliar issues.
Experience managing multiple matters and working with business stakeholders to resolve them.
Experience with U.S. legal matters and regulated businesses, insurance, fintech, consumer protection, or privacy is a plus.
While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.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 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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