Job Overview
Location
Toronto, Ontario
Job Type
Full-time
Category
Operations
Date Posted
May 12, 2026
Full Job Description
đź“‹ Description
- • As an Operations Associate (Legal & Compliance) at Jerry Technologies Inc., you will play a critical role in ensuring the company’s legal and regulatory integrity while driving innovation in compliance processes. This role is ideal for someone who thrives in a fast-paced startup environment and wants to make an immediate impact by owning end-to-end legal operations with a product and automation mindset.
- • 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 root cause and lead compliance training, audit operations for regulatory adherence, and partner with Engineering and Product teams to improve compliance-related product features and processes. You will also leverage AI and low-code tools to automate manual legal tasks, transforming repetitive work into scalable systems.
- • Jerry Technologies Inc. is a fast-growing, venture-backed startup with over $240M in funding and 60x revenue growth in five years. The company operates as a meritocracy where performance and ownership drive advancement, and you’ll be mentored by serial entrepreneurs and leaders from companies like Amazon, LinkedIn, McKinsey, and BCG. The legal team is lean and agile, offering significant autonomy and ownership from day one.
- • In this role, you will develop deep expertise in corporate compliance, intellectual property management, and regulatory risk mitigation while gaining hands-on experience in process automation, cross-functional collaboration with tech and product teams, and startup-scale operations. You’ll have the opportunity to build scalable systems that set industry benchmarks and directly contribute to Jerry.ai’s mission of simplifying car ownership through AI-powered innovation.
🎯 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 prompting
- • Interest in using AI or technology to optimize workflows, with preference for automated tools over manual processes
- • 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 a bias toward action
🏖️ 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
- • Mentorship from serial entrepreneurs and leaders from top-tier companies
- • Opportunity to work at a Forbes Top Startup Employer with significant growth trajectory
Skills & Technologies
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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