Operations Analyst (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 US and Canada, ensuring all filings are completed accurately and on time to maintain "Good Standing" status without oversight.
• Proactively monitor the company’s intellectual property footprint and initiate cease-and-desist workflows to protect the brand from infringement, including drafting legal notices and coordinating responses.
• Serve as the first line of defense for complex consumer escalations by investigating root causes, identifying compliance gaps, and developing strategic solutions that prevent recurrence.
• Design and lead compliance training initiatives that educate the broader workforce on regulatory obligations, risk areas, and best practices to foster a culture of accountability.
• Conduct comprehensive compliance audits across operations, identifying systemic risks and ensuring practices exceed baseline regulatory standards to set industry benchmarks.
• Partner directly with Engineering and Product teams to review product features and internal processes for legal and compliance risks, translating findings into actionable, systemic improvements.
• Automate manual legal and compliance tasks using AI tools and low-code platforms to create scalable, repeatable workflows that reduce human error and free up capacity for higher-impact work.
• Drive continuous improvement in compliance operations by identifying inefficiencies, proposing technical solutions, and measuring the impact of implemented systems on time savings and risk reduction.
• Maintain rigorous organizational discipline to ensure zero missed deadlines, accurate regulatory submissions, and flawless tracking of cross-functional compliance projects.
• Operate independently in a fast-paced, ambiguity-rich startup environment with high ownership, taking initiative to solve problems without predefined playbooks or manual guidance.
• Leverage data and technology to optimize legal workflows, preferring automated tools and spreadsheets over manual processes to increase scalability and reduce operational drag.
• Collaborate across departments to embed compliance into product development cycles, ensuring legal considerations are proactively addressed rather than retroactively patched.
• Contribute to building a compliance function that evolves with the company’s growth, scaling from reactive task execution to proactive, system-driven risk management.
• Maintain strict confidentiality and accuracy in handling sensitive legal, financial, and customer data as part of daily compliance and audit responsibilities.

🎯 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 without prompting
• Interest in using AI and 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
• Ability to thrive in high-performance, ambiguous startup environments with deep ownership and urgency
• Experience managing corporate compliance across multiple jurisdictions (US and Canada)

🏖️ 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

Onsite

Degree Required

Ready to Apply?

Apply Externally

You will be redirected to an external site to apply.

Jerry Technologies Inc.

Visit Website

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.

View Company Profile

Get more remote jobs like this

Subscribe to the weekly newsletter for similar remote roles and curated hiring updates.

Weekly remote jobs and featured talent.

No spam. Only curated remote roles and product updates. You can unsubscribe anytime.