[Hiring] Legal Operations Associate @Jerry.ai

Role Description

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
• 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.

Qualifications

• 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.

Requirements

• Use AI and low-code tools to replace manual legal tasks with workflows that run on their own.
• Work with our Legal Counsel on legal research, contract reviews, and other substantive projects as new questions come up.
• 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.
• Monitor Jerry’s intellectual property, find infringements, and initiate cease-and-desist workflows.
• Investigate complex escalations to their root cause, recommend fixes, and turn recurring issues into compliance training for teams across the company.
• Review products and processes for compliance risk and user friction, then work with Engineering and Product to fix the underlying issue.
• Lead audits across operations and keep watch on the highest-risk areas between them.

Benefits

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

Company Description

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.

Imagine having a trusted friend in your pocket who takes care of everything:

• Finds you the right car or home at the right price
• Locks in the best insurance rate without you lifting a finger
• Reminds you before that service appointment turns into an expensive repair
• Helps you sell at the best price when the time is right

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.