[Hiring] Legal Researcher @Jerry.ai

Role Description

As our Legal Researcher, you’ll work closely with our Legal Counsel and partner with teams across Jerry to research hard questions and turn your findings into decisions the business can act on. This role is built for high-performing law graduates who want a rigorous in-house legal career outside the law firm path. It’s also highly hands-on:

• Alongside substantive legal research and review, you’ll own recurring compliance and legal operations work and improve the systems and automations behind it.
• If you succeed, Jerry’s leaders make faster, better-informed decisions on legal risk, and you’ll have owned work that shapes how the company grows.

Qualifications

• A JD or LLM, with a record of high academic performance.
• Strong legal research and writing skills, with the ability to turn complex analysis into clear, practical recommendations.
• Strong organization and project-management skills, with the ability to manage multiple matters and deadlines at once.
• Demonstrated interest in using AI and technology to improve legal work, such as a tool, automation, or process you built yourself.

Requirements

• Research regulatory, consumer protection, and product questions, and turn your findings into clear recommendations business leaders can act on.
• Own complex consumer escalations and regulatory inquiries: find the root cause, identify potential legal issues, propose scalable fixes, and turn recurring issues into company-wide compliance training.
• Support review of features, flows, and policies with Product, Engineering, and Operations, and translate legal requirements into product and operational decisions.
• Manage entity compliance across US and Canadian jurisdictions, spotting risks early and building systems that prevent lapses.
• Lead audits across operations and keep watch on the highest-risk areas between them.
• Monitor for infringements and support enforcement strategy, including drafting cease-and-desist letters.
• Find repetitive legal work and replace it with AI, low-code, and automated workflows.

Benefits

• Comprehensive benefits package including health, dental, and vision coverage.
• Paid time off and 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. 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.
• We support remote work for most roles, but also have offices in Palo Alto, New York City, Chicago, and Toronto.