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Added 8 mins ago
R-
Temporary Fashion Associate - Heartland town center
RCL - Reitmans Canada Ltd/Ltée
Mississauga, ON
- Part-time
As a Fashion Associate, you will deliver personalized service and support daily store operations to ensure a welcoming, customer-first environment. From assisting in the fitting room to…
Added 1 hour ago
ON
Seasonal Associé aux ventes/Seasonal Retail Sales Associate - Promenades Gatineau
Old Navy
Gatineau, QC
- Part-time
En tant que Brand Associate, vous faites partie intégrante de notre équipe et incarnez notre marque auprès de nos clients. Vous avez pour mission de créer un lien avec eux en offrant un…
Added 1 hour ago
ON
Retail Sales Associate - Sunridge Mall
Old Navy
Calgary, AB
- Part-time
As a Brand Associate, you’re an integral part of our team and bring our brand to life for our customers. You’re responsible for engaging and connecting with our customers by providing…
Added 2 hours ago
LC
Associate Faculty - Clinical Nursing
Lambton College
Sarnia, ON
- Part-time
We recognize that structural barriers shape experiences and job qualifications, and therefore we seek to use employment equity to differentiate between candidates who meet the required…
Added 2 hours ago
LC
Associate Faculty - Welding
Lambton College
Sarnia, ON
- Part-time
We recognize that structural barriers shape experiences and job qualifications, and therefore we seek to use employment equity to differentiate between candidates who meet the required…
Added 2 hours ago
EI
Site Project Manager
Ecolab Inc.
Calgary, AB
- Full-time
Successful candidates will be required to undergo pre-hire background checks as a condition of employment.
Added 2 hours ago
EI
Brand Protection Advisor I
Ecolab Inc.
Saskatoon, SK
- Full-time
Comprehensive benefits package starting day 1 of employment including medical, dental, vision, stock purchase plan, tuition reimbursement and more!
Added 3 hours ago
R(
Temporary Fashion Associate - Heartland town center
Reitmans (Canada) Ltée/Ltd
Mississauga, ON
- Part-time
As a Fashion Associate, you will deliver personalized service and support daily store operations to ensure a welcoming, customer-first environment. From assisting in the fitting room to…
Added 4 hours ago
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Maintenance / Handyman Associate
Boardwalk
Calgary, AB
- Full-time
Offers of employment will be contingent on satisfactory Security Background Checks, Reference Checks, and Pre-employment Physical Testing where applicable.
Added 4 hours ago
*New Store Opening* - Chinook, Calgary, Canada
Reformation
Calgary, AB
You’ll get access to fertility care support through Carrot, and up to a $5,000 USD reimbursement for related fertility expenses after 1 year of employment.
Added 4 hours ago
SD
Front Store Manager, Salaried Full Time Flexible Shifts Greenlight Requisition
Shoppers Drug Mart
North Vancouver, BC
- Full-time
Acting as consultants, supporting internal customers and the Associate-Owners, you will get experience unique to the retail industry while working for an award-winning national brand.…
Added 4 hours ago
MC
Senior Salesforce Administrator
Make-A-Wish Canada
Toronto, ON
- Full-time
Dr. Jeremy Friedman, Associate Paediatrician-in-Chief, SickKids Hospital & Medical Advisor for Make-A-Wish^® Canada
Added 4 hours ago
MC
Marketing Specialist, Events/Spécialiste du marketing, événements
Make-A-Wish Canada
Montreal, QC
- Full-time
Dr. Jeremy Friedman, Associate Paediatrician-in-Chief, SickKids Hospital & Medical Advisor for Make-A-Wish^® Canada
Added 4 hours ago
RAS Senior Associate
Reckitt
Mississauga, ON
The Senior Regulatory Associate supports and leads regulatory activities across Reckitt’s Canadian portfolio, as required, developing practical regulatory strategies that support business…
Added 4 hours ago
HI
Commercial Lines Account Associate, Professional Liability
HUB International
Markham, ON
- Full-time
We’re looking for a strong Commercial Account Associate to support our professional liabilities accounts in Markham. This role involves working closely with Senior Team members of the…
Added 5 hours ago
R
Temporary Fashion Associate - Square one
RW&CO
Mississauga, ON
- Part-time
As a Fashion Associate, you will deliver personalized service and support daily store operations to ensure a welcoming, customer-first environment. From assisting in the fitting room to…
Added 5 hours ago
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Marketing Compliance Associate
Clarity (formerly Hiive)
Vancouver, BC
- Full-time
As a Marketing Compliance Associate at Clarity, you will review the marketing and communications that reach our customers, prospective customers, and the public. You will work with our…
Added 5 hours ago
HT
Maintenance Technician
Husky Technologies
Bolton, ON
- Full-time
Engineering, or a related field (e.g., Associate's degree in
Added 5 hours ago
EI
Territory Representative, Hospitality Sales & Service
Ecolab Inc.
Mississauga, ON · Richmond Hill, ON · Toronto, ON · Woodbridge, ON · Scarborough, Ontario
- Full-time
Successful candidates will be required to undergo pre-hire background checks as a condition of employment.
Added 6 hours ago
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Clinical Research Manager
RI-MUHC | Research Institute of the MUHC | #rimuhc
Montreal, QC
- Full-time
Added 6 hours ago
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Spécialiste Beauté, rémunéré(e) à l’heure temps partiel Quarts de travail flexibles
LinkedIn
Drummondville, QC
- Part-time
Associate Owners in the Pharmaprix network recognize Canada's diversity as an opportunity to better serve their communities, and strive to reflect the nation’s evolving diversity in the…
Added 6 hours ago
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Research Associate
RI-MUHC | Research Institute of the MUHC | #rimuhc
Montreal, QC
- Full-time
…motivated person to fill the position of full-time Research Associate. The team specializes in genetic white matter diseases, leukodystrophies, and related disorders. Under the direction of…
Added 6 hours ago
R-
Temporary Fashion Associate - Square one
RCL - Reitmans Canada Ltd/Ltée
Mississauga, ON
- Part-time
As a Fashion Associate, you will deliver personalized service and support daily store operations to ensure a welcoming, customer-first environment. From assisting in the fitting room to…
Added 6 hours ago
R-
Temporary Fashion Associate - Woodstock
RCL - Reitmans Canada Ltd/Ltée
Woodstock, ON
- Part-time
As a Fashion Associate, you will deliver personalized service and support daily store operations to ensure a welcoming, customer-first environment. From assisting in the fitting room to…
Added 6 hours ago
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Fellowship and Bursary Administrative Assistant
RI-MUHC | Research Institute of the MUHC | #rimuhc
Montreal, QC
- Full-time
Updates departmental funding timelines with the Associate Chair of Education in line with McGill Postgraduate Medical Education (PGME) guidelines, updates, circulates for review and posts…

Jerry.ai

Legal Operations Associate (Remote)

Remote, Canada

Remote

$65,000 to $80,000 CAD / year · Full-time

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Job details

Pay: $65,000 to $80,000 CAD / year
Job type: Full-time
Workplace: Remote
Posting language: English
Posted: Nov 4, 2026

Original job description

More than 80% of Americans own a car and see it as a fundamental necessity, yet the experience of owning one is stuck in the 90s. At Jerry.ai, we are building the first app to manage it all. Since launching in 2019, we’ve reached 5M+ customers, raised $240M+, scaled revenue 70X, and achieved profitability in 2024.

Jerry operates across the US and Canada, and our legal team keeps all of it running: entity filings, IP protection, compliance audits, consumer escalations, regulatory changes, and the systems behind them. The team is small, so this role comes with real scope early. You’ll own Jerry’s legal and compliance operations: make sure recurring work is done right, run the programs that need judgment, and keep rebuilding them with AI and low-code tools, so a small team can do the work of a much larger one.

The person who succeeds in this role is a natural driver: someone who owns their work from start to finish, solves complex problems without a manual, and has the grit to thrive in a startup environment. If you are eager to sit at the intersection of law, technology, and AI-driven efficiency, we want to hear from you.

Why You Will (Or Won’t) Like Working Here

Real ownership early: You report directly to our Legal Counsel and work closely with them across the team’s full scope. You’ll own a set of compliance programs for the long term, and you’ll be the first point of contact for teammates who run day-to-day compliance work.
Room to build: Many of our legal processes are still being optimized. You’ll decide how they should work and build the systems behind them.
Building and operating: Alongside the building, a large share of the job is recurring work: filings, deadlines, audits, complaint responses, and quality checks that have to be done exactly right, every time. Your accuracy keeps Jerry in good standing in every jurisdiction, and people who enjoy both sides of the role do well here.
Growth that tracks results: You’ll learn from leaders who come from Amazon, Better, LinkedIn, McKinsey, BCG, and Bain. Promotion is based on performance and ownership alone, so strong work moves you forward fast.

What You’ll Own

Compliance operations: Run, review, and quality-check the recurring compliance work, including entity maintenance, privacy requests, and licensing support.
Marketing compliance and audits: Run TCPA and Do Not Call audits, monitor opt-outs, and keep marketing guidelines current. Check the accuracy of AI-powered audits, and design new audit programs with sampling plans and scoring rubrics.
Consumer escalations: Investigate complex escalations to their root cause, work with Product, Operations, and Engineering on the fix, and turn recurring issues into compliance training for teams across the company.
Regulatory change and readiness: Track regulatory changes, along with issues surfaced by complaints and audits, and see each one through to action. Keep Jerry ready to answer regulator inquiries, carrier audits, and partner diligence quickly.
Legal team support: Support contract renewals, legal research, and product reviews with intake, fact gathering, trackers, and follow-up.
Automation and AI: Replace manual legal tasks with AI and low-code workflows, and own the reliability of every script, report, and AI tool the team depends on.

Who You Are

A Closer: You track every open item until it’s done, and you find the answer yourself before asking someone else for it.
A Builder: The second time you do a task by hand, you start working out how to automate the third. You reach for a spreadsheet or a low-code tool before a manual checklist.
A Zero-Error Operator: Regulatory filings and audits leave no room for mistakes, and you work accordingly. You keep your own system so no deadline or cross-functional project slips.
A Root-Cause Investigator: You don’t stop at the symptom. You dig into the records, find what actually went wrong, and follow the fix through until it’s done.
A Proactive Communicator: You provide updates without being chased, flag blockers early, and make sure teammates know what happens next.
Comfortable with ambiguity: You can take an unclear brief, define the problem yourself, and move on it with urgency. You also know which calls to make yourself and which to escalate.

What You’ll Bring

A Bachelor’s degree from an academically rigorous program, with a record of high performance.
A track record of owning projects start to finish and solving problems without being told how, at school, at work, or on your own.
Hands-on experience using AI and technology to improve how work gets done, such as a tool, automation, or process you built yourself, and the habit of checking AI output before relying on it.
Experience in compliance, legal operations, audit, or another regulated environment is a plus, but not required.

While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.

Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.

Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.

Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai

The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.

We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.

About Jerry.ai

Jerry is building the first AI-powered advisor to manage all your physical assets.

Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey - buying, insuring, maintaining, repairing, selling - is fragmented, complicated, and expensive.

Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.

We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.

Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay - we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.

We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.

We support remote work for most roles, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.

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More about this job

Responsibilities

You will manage legal and compliance operations, including entity maintenance, audits, and consumer escalations. Additionally, you will leverage AI and low-code tools to automate manual legal processes and improve team efficiency.

Requirements

Candidates must hold a Bachelor's degree from an academically rigorous program and demonstrate a track record of project ownership. Experience in legal operations, compliance, or audit environments is preferred, along with hands-on experience using technology to improve workflows.

Skills

Legal operations
Compliance
Audit management
Regulatory compliance
Process automation
Low-code tools
AI tools
Contract management
Data analysis
Project management
Problem solving
Communication
Risk assessment
Entity maintenance
Consumer escalations
Legal research

Benefits

Health insurance
Dental insurance
Vision insurance
Paid time off
Paid parental leave
401(k) plan
RRSP plan
Employer matching
Wellness benefits
Equity grants

Remote locations

Arizona, United States
California, United States
Colorado, United States
Florida, United States
Georgia, United States
Illinois, United States
Massachusetts, United States
North Carolina, United States
New Jersey, United States
Nevada, United States
New York, United States
Oregon, United States
Tennessee, United States
Texas, United States
Utah, United States
Virginia, United States
Ontario, Canada

Remote locations (standardized)

Arizona, United States
California, United States
Colorado, United States
Florida, United States
Georgia, United States
Illinois, United States
Massachusetts, United States
Nevada, United States
New Jersey, United States
New York, New York, United States
North Carolina, United States
Ontario, Canada
Oregon, United States
Tennessee, United States
Texas, United States
Utah, United States
Virginia, United States

Visa sponsorship

Not detected in the job text

Keywords

Legal Operations
Compliance
Audit
AI
Low-code
Automation
Regulatory
Entity maintenance
Privacy
TCPA
Marketing compliance
Contract renewals
Fintech
Insurtech
Startup
Project management
Risk management
Data integrity
Process optimization
Workflow design

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