Legal Operations Associate (Remote)

Jerry Technologies Inc.

Job Overview

Location

Toronto, Ontario

Job Type

Full-time

Full Job Description

📋 Description

• As a Legal Operations Associate at Jerry Technologies Inc., you will play a pivotal role in scaling legal functions through automation and process innovation, directly supporting the company’s rapid growth as a Forbes Top Startup Employer with $240M in funding and 60x revenue growth in five years.
• Day to day, you will own entity compliance across the US and Canada, monitor and protect intellectual property by identifying infringements and initiating cease-and-desist workflows, investigate consumer escalations to drive compliance training, audit operations for regulatory excellence, and partner with Engineering and Product teams to implement systemic improvements using AI and low-code tools.
• You will join a lean, fast-paced legal team at a mission-driven startup backed by serial entrepreneurs from Amazon, LinkedIn, McKinsey, and BCG, where meritocracy drives advancement and your work sits at the intersection of law, technology, and AI-driven efficiency.
• In this role, you will develop expertise in legal operations automation, gain hands-on experience with AI and low-code platforms, strengthen cross-functional collaboration with product and engineering teams, and build a track record of owning complex compliance initiatives from start to finish in a high-growth environment.

🎯 Requirements

• Bachelor’s degree from an academically rigorous program with demonstrated high performance
• Proven track record of extreme resourcefulness and a driver mindset — able to find answers independently and close loops without direction
• Interest in using AI or technology to optimize workflows, preferring automated tools over manual processes
• Impeccable attention to detail with a zero-error mentality in regulatory filings and compliance audits
• Ability to thrive in high-performance, ambiguous environments with urgency, ownership, and results-driven focus

🏖️ 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 and equity opportunities as part of total rewards
• Opportunity to work remotely with a innovative, mission-driven team at a rapidly scaling startup

Skills & Technologies

Junior

Onsite

Degree Required

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Jerry Technologies Inc.

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About Jerry Technologies Inc.

Jerry Technologies offers a mobile-first AI platform that automatically compares insurance quotes, refinances auto loans, and shops for home and renters coverage. Users submit photos of existing policies, and the app retrieves and compares rates from carriers to find lower premiums or better terms. The company earns commissions from insurers when policies are switched or originated through its platform, serving consumers seeking to reduce recurring auto and home expenses without manual comparison shopping.

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