This is a hands on in house legal role for a recent law graduate. The work covers contract drafting and negotiation, regulatory and licensing research, product and compliance reviews, and handling consumer escalations and regulatory inquiries. A solid candidate brings solid legal research and writing, careful contract review, and the organization to juggle many matters and deadlines at once.

How it fits the AI era

Much of the research and first pass contract review can be sped up with AI tools, so the role leans more on judgment, accuracy, and turning findings into clear recommendations leaders can act on. The company is an AI driven insurance and car ownership platform, so legal questions about product features and regulation come up quickly and often. What stays human is spotting the real issue, weighing risk, and explaining a practical path forward.

How it builds AI experience

Working here means seeing how AI products in insurance and consumer finance raise privacy, licensing,



and consumer protection questions, which builds useful judgment for a legal career. A candidate can prepare by getting comfortable with legal research tools and by learning to check and verify machine output rather than trust it. Building a habit of automating repeated manual tasks, as the posting asks, would also help.

Worth showing

- Legal research and writing
- Contract drafting and review
- Regulatory and licensing research
- Clear practical recommendations

This is our own read, written from the employer's posting and the company's Spotlight. The employer's posting is the source of truth for the role.

About Jerry

A free app that uses AI to shop car insurance across 100+ insurers, per the company, and manage the rest of car ownership, maintenance, recalls and refinancing, in one place.

📌 Legal Researcher (Winnipeg)
🏢 present of AI
📍 Winnipeg