Job Overview
Location
Toronto, Ontario
Job Type
Full-time
Category
DevOps
Date Posted
May 19, 2026
Full Job Description
đź“‹ Description
- • Own entity compliance across the U.S. and Canada, managing all corporate filings and state communications independently to ensure all entities remain in good standing.
- • Monitor and protect the company’s intellectual property by identifying infringements and drafting/launching cease-and-desist workflows without supervision.
- • Serve as the first line of defense for complex consumer escalations, investigating root causes, proposing strategic resolutions, and leading compliance training initiatives company-wide.
- • Partner directly with Engineering and Product teams to review product workflows and operational processes for legal compliance, identifying friction points and proposing systemic improvements to mitigate risk.
- • Lead internal compliance audits across operations, proactively monitoring key risk areas to ensure practices exceed baseline regulatory standards and establish industry benchmarks.
- • Automate manual legal tasks using AI tools and low-code platforms, designing scalable workflows that replace checklists and reduce human dependency on repetitive compliance activities.
- • Operate with a product-focused mindset, treating legal operations as a system to be optimized—not a set of tasks to be completed—by continuously seeking ways to increase efficiency and reduce manual effort.
- • Work autonomously in a fast-paced, high-ambiguity startup environment, taking full ownership of projects from initiation to closure without predefined playbooks or hand-holding.
- • Maintain a zero-error standard in regulatory filings and audit documentation, ensuring absolute precision and timeliness in all compliance-related deliverables.
- • Drive cultural change by embedding compliance and automation best practices into team workflows, influencing cross-functional teams through data-driven recommendations and demonstrable results.
- • Collaborate across departments including Engineering, Product, Customer Success, and Operations to align legal requirements with business goals and user experience.
- • Continuously evaluate emerging legal tech tools and AI applications to identify opportunities for further operational streamlining and scalability.
- • Document all processes, systems, and workflows to enable knowledge transfer and team scalability as the legal operations function grows.
- • Respond to evolving regulatory landscapes in real time, adapting internal procedures quickly to maintain compliance in multiple jurisdictions.
- • Contribute to the development of legal tech initiatives by providing user feedback and requirements to product teams building AI-driven legal solutions.
- • Represent the legal team in cross-functional meetings with authority, clarity, and strategic insight, translating legal constraints into actionable product and operational changes.
- • Track and report on compliance metrics and audit outcomes, using data to demonstrate efficiency gains and risk reduction to leadership.
🎯 Requirements
- • A Bachelor’s degree from an academically rigorous program with demonstrated high performance
- • A proven track record of extreme resourcefulness and an innate need to close loops independently
- • Interest in using AI and technology to optimize workflows, preferring automated tools over manual checklists
- • Impeccable attention to detail with a zero-error mentality toward regulatory filings and compliance audits
- • Ability to thrive in high-performance, ambiguous environments with a deep sense of urgency and full ownership of outcomes
🏖️ Benefits
- • Health, dental, and vision coverage
- • Paid time off
- • Paid parental leave
- • 401(k) plan with employer matching
- • Wellness benefits
- • Opportunities for equity grants
Skills & Technologies
Junior
Onsite
Degree Required
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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