Legal Operations Associate (Remote)

Jerry Technologies Inc.

Job Overview

Location

Toronto, Ontario

Job Type

Full-time

Full Job Description

📋 Description

• As a Legal Operations Associate at Jerry Technologies Inc., you will play a pivotal role in scaling legal functions through innovation, automation, and proactive risk management in a high-growth startup environment. This role is critical to ensuring regulatory compliance, protecting intellectual property, and enabling product teams to move fast while staying compliant—directly supporting Jerry.ai’s mission to revolutionize car ownership through AI-driven solutions.
• You will own entity compliance across the U.S. and Canada, ensuring all corporate entities remain in 'Good Standing' by managing state filings, annual reports, and regulatory deadlines independently and with zero tolerance for error.
• You will monitor and protect Jerry.ai’s intellectual property by identifying potential infringements, gathering evidence, and initiating cease-and-desist workflows in collaboration with legal counsel to safeguard the brand and its innovations.
• You will serve as the first responder to complex consumer escalations, investigating root causes, developing strategic solutions, and leading compliance training initiatives that educate cross-functional teams and reduce organizational risk.
• You will partner with Engineering and Product teams to review features and processes for compliance risks, identifying user friction or regulatory gaps and driving systemic improvements that embed compliance into product design from the outset.
• You will lead compliance audits across operations, proactively monitoring high-risk areas, documenting findings, and implementing corrective actions that not only meet but exceed industry benchmarks for regulatory excellence.
• You will leverage AI, low-code platforms, and automation tools to transform repetitive legal tasks—such as contract tracking, deadline management, and report generation—into scalable, self-service workflows that increase efficiency and reduce manual effort.
• You will thrive in a meritocratic, high-performance culture where ownership, initiative, and results are valued over tenure, working directly with serial entrepreneurs and leaders from Amazon, LinkedIn, McKinsey, and BCG who prioritize impact and innovation.
• You will gain deep exposure to the intersection of law, technology, and AI in a fast-scaling startup, developing rare expertise in legal operations automation, regulatory strategy, and cross-functional influence that positions you for rapid career growth in legal tech, compliance, or product law.

🎯 Requirements

• Bachelor’s degree from an academically rigorous institution with a record of high academic performance.
• Proven track record of extreme resourcefulness and initiative—consistently solving problems independently and closing loops without needing direction.
• Strong interest or experience in using AI, spreadsheets, or low-code tools to automate manual workflows and improve operational efficiency.
• Impeccable attention to detail with a 'zero-error' mindset, particularly in regulatory filings, compliance tracking, and deadline management.
• Ability to thrive in ambiguous, fast-paced environments with a strong sense of urgency, taking full ownership of outcomes and delivering results under pressure.

🏖️ Benefits

• Comprehensive health, dental, and vision coverage for regular employees.
• Paid time off, paid parental leave, and wellness benefits to support work-life balance and well-being.
• 401(K) plan with employer matching to support long-term financial security.
• Opportunities for equity grants as part of total compensation, aligning employee success with company growth.
• Access to mentorship from serial entrepreneurs and industry leaders who have scaled companies at Amazon, LinkedIn, McKinsey, BCG, and Bain.
• Merit-based culture where promotions are driven by performance, ownership, and impact—not tenure or seniority.

Skills & Technologies

Junior

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.