This is a hands-on legal operations role in a small team, reporting to the Legal Counsel. The work mixes steady, deadline-driven tasks like entity filings and audits with building automations to replace manual work. A solid candidate is organized, accurate, and quick to teach themselves, and has already built a tool or process that saved time.

How it fits the AI era

The role is explicitly about using AI and low-code tools to turn repeated legal tasks into workflows that run on their own, so a small team can cover more ground. Tasks like tracking filings, first-pass research, and spotting trademark misuse are good candidates for automation. Judgment on compliance risk, working out the root cause of customer complaints, and being accountable for filings that must be exactly right stay with a person.

How it builds AI experience

The company runs an AI-driven app that shops insurance across many insurers and handles car ownership tasks, so the legal questions touch consumer protection,



insurance, and product design. In this seat, someone would gain practice designing automated legal workflows and reviewing product features with Engineering and Product. To build this experience beforehand, create a small automation, such as a deadline tracker or intake form, and write up how it works.

Worth showing

- A workflow you automated yourself
- Careful deadline and filing tracking
- Root cause problem solving
- Comfort with low-code tools

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 Operations Associate (Winnipeg)
🏢 present of AI
📍 Winnipeg