Job Overview
Location
Toronto, Ontario
Job Type
Full-time
Category
Operations
Date Posted
May 12, 2026
Full Job Description
đź“‹ Description
- • As an Operations Analyst on the legal and compliance team at Jerry Technologies Inc., you will play a critical role in ensuring regulatory adherence and brand protection while driving innovation through automation and process improvement.
- • 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 engineering and product teams to identify and resolve compliance risks through systemic improvements.
- • You will join a lean, fast-paced legal team within a high-growth startup backed by $240M in funding and recognized as a Forbes Top Startup Employer, where mentorship from serial entrepreneurs and leaders from Amazon, LinkedIn, McKinsey, and more fosters a meritocratic culture.
- • In this role, you will develop expertise in legal operations, compliance automation, and AI-driven workflow optimization, gaining hands-on experience in scaling processes and influencing product design from a compliance-first perspective.
🎯 Requirements
- • Bachelor’s degree from an academically rigorous program with demonstrated high performance
- • Proven track record of extreme resourcefulness and a driver mindset with a need to close loops
- • 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 environments with comfort in ambiguity, urgency, and ownership of outcomes
🏖️ 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 with a mission-driven team at a Forbes Top Startup Employer
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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