Job Overview
Location
Toronto, Ontario
Job Type
Full-time
Category
Operations
Date Posted
May 4, 2026
Full Job Description
đź“‹ Description
- • As an Operations Analyst (Legal & Compliance) at Jerry Technologies, Inc., you will play a critical role in ensuring regulatory adherence and operational excellence within a fast-growing, AI-driven startup environment. This role is pivotal in maintaining corporate entity compliance, protecting intellectual property, and driving systemic improvements that scale legal and compliance functions through technology.
- • Day to day, you will own entity compliance across the US and Canada, monitor and respond to intellectual property infringements, investigate consumer escalations, lead compliance audits, and partner with Product and Engineering teams to identify and resolve compliance risks. You will also leverage AI and low-code tools to automate manual legal workflows, turning repetitive tasks into scalable systems.
- • You will join a lean, high-impact legal team within Jerry.ai, a Forbes Top Startup Employer backed by $240M in funding and known for 60x revenue growth in five years. The company fosters a meritocratic culture where performance and ownership drive advancement, and you’ll be mentored by serial entrepreneurs and leaders from Amazon, LinkedIn, McKinsey, and other elite organizations.
- • In this role, you will develop deep expertise in regulatory compliance, legal operations, and process automation. You’ll gain hands-on experience using AI to optimize workflows, influence product design for compliance, and build scalable systems—positioning yourself at the forefront of legal tech innovation in a high-growth startup.
🎯 Requirements
- • Bachelor’s degree from an academically rigorous program with demonstrated high performance
- • Proven track record of extreme resourcefulness and a driver mindset—someone who finds answers before asking questions and closes loops independently
- • Interest in using AI or technology to optimize workflows, with preference for spreadsheets or automated tools over manual checklists
- • Impeccable attention to detail and a zero-error mentality in regulatory filings and compliance audits
- • Ability to thrive in high-performance, ambiguous environments with urgency, ownership, and comfort operating without clear direction
🏖️ Benefits
- • Comprehensive benefits package including health, dental, and vision coverage
- • Paid time off, paid parental leave, and 401(K) plan with employer matching
- • Wellness benefits and equity opportunities as part of total rewards
- • Opportunity to work at a Forbes Top Startup Employer with mentorship from serial entrepreneurs and leaders from Amazon, LinkedIn, McKinsey, BCG, and Bain
- • Meritocratic culture where promotion is based on performance, ownership, and results—not tenure
Skills & Technologies
About Jerry Technologies, Inc.
Jerry is a technology company focused on simplifying and personalizing the car ownership experience. They offer a mobile app that acts as a digital assistant for car owners, providing services such as insurance comparison and purchasing, maintenance scheduling, roadside assistance, and parking assistance. Jerry aims to reduce the stress and cost associated with owning a vehicle by leveraging AI and data analytics to offer tailored solutions and competitive pricing. Their platform connects users with a network of service providers and insurance carriers, streamlining the entire car ownership lifecycle.
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