Legal Operations Associate (Remote)

About the role

Jerry.ai is building the first app to manage car ownership end to end. Since launching in 2019, the company has reached 5M+ customers, raised $240M+, scaled revenue 70X, and achieved profitability in 2024. Operating across the US and Canada, the legal team handles 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, enabling a small team to do the work of a much larger one. This role reports directly to Legal Counsel and sits at the intersection of law, technology, and AI-driven efficiency.

Why you’ll like working here

• Real ownership early: You report directly to Legal Counsel and work across the team’s full scope. Projects are yours from start to finish.
• Room to build: Many legal processes are still being optimized. You’ll decide how they should work and build the systems behind them.
• Building and operating: A large share of the job is recurring work — filings, deadlines, and audits that must be done exactly right, every time. Your accuracy keeps Jerry in good standing in every jurisdiction.
• Growth that tracks results: Learn from leaders from Amazon, Better, LinkedIn, McKinsey, BCG, and Bain. Promotion is based on performance and ownership alone.

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 Legal Counsel on legal research, contract reviews, and other substantive projects as new questions arise.
• 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 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 monitor 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.
• 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 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.

Location requirements

Jerry.ai hires 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. Applications from candidates residing elsewhere cannot be accepted at this time.

Benefits

• Health, dental, and vision coverage
• Paid time off
• Paid parental leave
• 401(K) plan with employer matching
• Wellness benefits
• Equity opportunities may be part of the total rewards package

About Jerry.ai

Jerry is building the first AI-powered advisor to manage all your physical assets — car, home, motorcycle, and beyond. Every step of ownership (buying, insuring, maintaining, repairing, selling) is fragmented, complicated, and expensive. Jerry acts as a trusted friend in your pocket: finding the right car or home at the right price, locking in the best insurance rate, reminding you before a service appointment turns into an expensive repair, and helping you sell at the best price. Started with car insurance in 2019, became a top-3 U.S. broker, then added driving insights, diagnostics, and a repair marketplace. Now expanding into home, motorcycle, RV, and more. Led by serial entrepreneurs and backed by Y Combinator, the team includes talent from Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Culture is the #1 reason people join and stay — a small, mighty team of competitive but kind owners who care deeply about quality and impact. Consistently ranked among Y Combinator’s Top Companies, Forbes and Statista’s Best Startup Employers, and recognized for fintech/insurtech innovation, workplace culture, and leadership. Remote work supported for most roles; offices in Palo Alto, New York City, Chicago, and Toronto.