Operations Associate (Legal & Compliance)

Jerry Technologies Inc.

Job Overview

Location

Toronto, Ontario

Job Type

Full-time

Full Job Description

📋 Description

• As an Operations Associate (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 scalable growth by ensuring entity compliance, protecting intellectual property, and mitigating risk across jurisdictions. You will not only uphold standards but actively redefine them through automation and cross-functional collaboration, making an immediate and measurable impact in a high-growth, mission-driven startup environment.
• Day to day, you will own entity compliance by managing all state and federal filings to maintain 'Good Standing' status for corporate entities across the U.S. and Canada, including preparing and submitting annual reports, responding to state inquiries, and tracking renewal deadlines without oversight. You will monitor and enforce intellectual property rights 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, document findings, and develop strategic recommendations while designing and delivering compliance training programs that educate teams on evolving regulatory expectations. You will partner with Product and Engineering teams to review features and workflows for compliance risks, translating legal requirements into actionable product improvements that reduce user friction and regulatory exposure. You will lead internal compliance audits by establishing monitoring protocols, conducting risk assessments, and ensuring adherence to both baseline regulations and Jerry’s elevated internal benchmarks. Finally, you will leverage AI, low-code platforms, and automation tools to replace manual legal tasks—such as docket tracking, document generation, and compliance checklists—with scalable, self-service workflows that increase efficiency and reduce human error.
• Jerry Technologies Inc. is a Forbes Top Startup Employer backed by $240M in funding and experiencing 60x revenue growth over five years, operating at the forefront of AI-driven innovation in the automotive and financial services space. The legal and compliance team is lean, agile, and deeply integrated with product and engineering, fostering a culture where ownership, initiative, and technical curiosity are rewarded. You will work alongside serial entrepreneurs and industry leaders from companies like Amazon, LinkedIn, McKinsey, and BCG, in an environment that values meritocracy over tenure and empowers individuals to solve ambiguous problems with creativity and rigor.
• In this role, you will develop rare hybrid expertise at the nexus of legal operations, regulatory technology, and process automation—skills that are increasingly valuable in scaling tech companies. You will gain hands-on experience using AI and low-code tools to transform traditional legal functions into scalable systems, positioning yourself as a forward-thinking compliance operator. You will also sharpen your ability to navigate ambiguity, drive cross-functional alignment, and deliver measurable outcomes in a fast-paced startup, building a track record of ownership and impact that accelerates career growth in operations, legal tech, or product compliance.

🎯 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 manual workflows.
• 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.
• Wellness benefits and equity opportunities as part of the total rewards package.
• Opportunity to work with a mission-driven team at a Forbes Top Startup Employer with significant traction and growth.
• Exposure to mentorship from serial entrepreneurs and leaders who have scaled companies like Amazon, LinkedIn, and McKinsey.

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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