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. 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.
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.
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. 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. Promotion is based on performance alone, so strong work moves you forward fast. Commercial agreements: 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: Work with colleagues handling recurring compliance operations and elevate material risks. Emerging issues and legal processes: Take on recent legal questions as Jerry launches products and enters partnerships. You develop a recommendation, explain your reasoning clearly, and balance legal risk with business objectives. You keep matters moving, manage deadlines, and follow issues through implementation. You review every contract and filing with total precision, down to defined terms, dates, and cross-references. A JD or LLM, with a record of high academic performance. 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. S. legal matters and regulated businesses, insurance, fintech, consumer protection, or privacy is a plus. 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. 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.
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 [email protected] 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. 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 role

📌 Associate Counsel (Winnipeg)
🏢 Jerry
📍 Winnipeg