Operations Analyst (Legal & Compliance)

Jerry Technologies Inc.

Job Overview

Location

Toronto, Ontario

Job Type

Full-time

Full Job Description

📋 Description

• As an Operations Analyst (Legal & Compliance) at Jerry Technologies Inc., you will play a pivotal role in safeguarding the company’s legal and regulatory standing while driving innovation in compliance processes. This role sits at the critical intersection of law, technology, and operational excellence, where your work directly enables the company to scale responsibly in a highly regulated industry. You will not only ensure adherence to complex corporate and intellectual property requirements across the U.S. and Canada but also pioneer automation and process improvements that transform how legal and compliance functions operate in a fast-growing startup.
• Day to day, you will own entity compliance by managing all state filings and maintaining 'Good Standing' status for corporate entities across jurisdictions, independently handling reports and responding to state requests. You will actively monitor and protect the company’s intellectual property by identifying potential infringements, gathering evidence, and initiating cease-and-desist workflows in coordination with legal counsel. As the first responder to complex consumer escalations, you will investigate root causes, develop strategic solutions, and lead compliance training initiatives that educate teams and reduce organizational risk. You will partner closely with Engineering and Product teams to review workflows and user experiences, identifying compliance risks or friction points and co-designing systemic improvements. You will lead proactive compliance audits across operations, monitoring key risk areas to ensure practices not only meet but exceed regulatory benchmarks. Finally, you will leverage AI, low-code platforms, and automation tools to replace manual legal tasks—such as tracking deadlines, generating reports, or managing document workflows—with scalable, intelligent systems that increase efficiency and reduce human error.
• Jerry Technologies Inc. is a high-growth, mission-driven startup recognized as a Forbes Top Startup Employer, backed by $240M in funding and demonstrating 60x revenue growth over five years. The company fosters a meritocratic culture where advancement is based on impact, ownership, and results—not tenure—and offers direct mentorship from serial entrepreneurs and industry leaders who have scaled organizations at Amazon, LinkedIn, McKinsey, BCG, and Bain. The legal and compliance team operates as a lean, agile unit within a broader mission to revolutionize car ownership through AI-powered innovation, giving you the opportunity to work alongside engineers, product managers, and operators who are equally committed to solving real-world problems at scale.
• In this role, you will develop deep expertise in regulatory compliance, intellectual property management, and operational risk mitigation while gaining hands-on experience in applying AI and automation to traditionally manual legal processes. You will sharpen your product-minded problem-solving skills by collaborating with cross-functional teams to build scalable solutions, positioning yourself at the forefront of legal tech innovation. Success in this role will not only establish you as a trusted compliance partner within the organization but also equip you with rare, high-value skills in legal operations, process automation, and risk-driven product collaboration—competencies that are increasingly sought after in modern, technology-forward enterprises.

🎯 Requirements

• Bachelor’s degree from an academically rigorous program with demonstrated high academic performance
• Proven track record of extreme resourcefulness and a driver mindset—consistently finding answers independently and closing loops without prompting
• Strong interest in leveraging AI, spreadsheets, or low-code tools to automate and optimize workflows over relying on manual processes
• Impeccable attention to detail with a 'zero-error' mentality, particularly in regulatory filings, compliance audits, and deadline management
• Ability to thrive in high-performance, ambiguous environments with a deep sense of urgency and full ownership of outcomes

🏖️ Benefits

• Comprehensive health, dental, and vision coverage for regular employees
• Paid time off, paid parental leave, and access to a 401(K) plan with employer matching
• Equity grant opportunities as part of the total rewards package, aligned with job-related factors and market conditions

Skills & Technologies

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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