Operations Associate (Legal & Compliance)

Jerry Technologies Inc.

Job Overview

Location

Toronto, Ontario

Job Type

Full-time

Full Job Description

📋 Description

• Own end-to-end entity compliance for corporate entities across the U.S. and Canada, including filing state reports and responding to government requests without supervision.
• Monitor and protect the company’s intellectual property by identifying infringements and initiating cease-and-desist workflows independently.
• Serve as the first point of contact for complex consumer escalations, investigating root causes, proposing strategic resolutions, and designing compliance training programs for company-wide implementation.
• Conduct compliance audits across operational functions, proactively identifying risk areas and ensuring practices exceed baseline regulatory standards to set industry benchmarks.
• Partner directly with Engineering and Product teams to review product workflows and processes for legal and compliance risks, translating findings into systemic product improvements.
• Automate repetitive legal and compliance tasks using AI tools and low-code platforms, replacing manual checklists with scalable, self-sustaining systems.
• Drive process innovation by identifying inefficiencies in legal operations and implementing technology-driven solutions that reduce manual effort and increase accuracy.
• Maintain a zero-error standard for all regulatory filings, audit documentation, and compliance records with meticulous attention to detail and deadline discipline.
• Operate autonomously in a fast-paced, ambiguity-rich startup environment with high ownership of outcomes and no hand-holding.
• Collaborate cross-functionally across departments to embed compliance into product development, customer support, and operational workflows.
• Continuously seek ways to optimize legal workflows using data, automation, and technology—prioritizing tools like spreadsheets, AI assistants, and workflow builders over manual processes.
• Represent the legal team in cross-departmental initiatives by translating legal requirements into actionable, scalable operational procedures.
• Maintain up-to-date knowledge of evolving state and federal compliance requirements affecting corporate entities and consumer-facing operations.
• Act as a proactive problem-solver who anticipates risks before they escalate, closing loops independently without being prompted.
• Contribute to building a culture of compliance excellence by educating teams, documenting processes, and championing best practices across the organization.
• Leverage company resources, including AI tools and internal systems, to scale legal operations without proportional increases in headcount.
• Deliver high-quality outputs under tight timelines, balancing multiple priorities without compromising accuracy or regulatory integrity.

🎯 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/technology to optimize workflows, preferring automated tools over manual checklists
• Impeccable attention to detail with a zero-error mentality for regulatory filings and compliance audits
• Comfort operating with ambiguity in high-performance environments, taking full ownership of outcomes

🏖️ Benefits

• Health, dental, and vision coverage
• Paid time off
• Paid parental leave
• 401(k) plan with employer matching
• Wellness benefits
• Equity grant opportunities

Skills & Technologies

Junior

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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