Jobs in Canada

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Added 10 mins ago
SD
Pharmacy Assistant, Hourly Part Time Flexible Shifts Greenlight Requisition
Shoppers Drug Mart
Almonte, ON
- Part-time
Each store has an Associate-Owner, so you will work for a local business owner while having the support of a national brand. Benefit from a purchase discount program, flexible and varied…
Added 10 mins ago
SD
Front Store Supervisor, Hourly Part Time Flexible Shifts
Shoppers Drug Mart
Toronto, ON
- Part-time
Each store has an Associate-Owner, so you will work for a local business owner while having the support of a national brand. Benefit from a purchase discount program, flexible and varied…
Added 10 mins ago
SD
Pharmacy Assistant, Hourly Full Time Flexible Shifts Greenlight Requisition
Shoppers Drug Mart
Belleville, ON
- Full-time
Each store has an Associate-Owner, so you will work for a local business owner while having the support of a national brand. Benefit from a purchase discount program, flexible and varied…
Added 10 mins ago
SD
Front Store Supervisor, Hourly Part Time Flexible Shifts Greenlight Requisition
Shoppers Drug Mart
Kimberley, BC
- Part-time
Each store has an Associate-Owner, so you will work for a local business owner while having the support of a national brand. Benefit from a purchase discount program, flexible and varied…
Added 10 mins ago
SD
Pharmacy Assistant, Hourly Part Time Day
Shoppers Drug Mart
Niagara Falls, ON
- Part-time
Each store has an Associate-Owner, so you will work for a local business owner while having the support of a national brand. Benefit from a purchase discount program, flexible and varied…
Added 10 mins ago
SD
Pharmacy Assistant, Hourly Part Time Day Greenlight Requisition
Shoppers Drug Mart
Regina, SK
- Part-time
Each store has an Associate-Owner, so you will work for a local business owner while having the support of a national brand. Benefit from a purchase discount program, flexible and varied…
Added 25 mins ago
J
Legal Operations Associate, Compliance & Automation
Jerry.ai
Remote, Canada
- $65,000 to $80,000 CAD / year
- Full-time
- Remote
Legal team support: Support contract renewals, legal research, and product reviews with intake, fact gathering, trackers, and follow-up.
Added 40 mins ago
WC
(CAN) Pharmacy Assistant
Walmart Canada
Victoria, BC
- Full-time
Clerical Organization, filing prescriptions, invoices, reports, correspondence and memos and completing any administrative support functions assigned (i.e. journals, accounts receivable,…
Added 40 mins ago
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Administrative Assistant
Aker Solutions
Fort McMurray, AB
- Full-time
Our Asset Integrity Management team in Fort McMurray, Alberta, is currently seeking an Administrative Assistant to support project activities. This position requires the successful…
Added 40 mins ago
TU
Postdoctoral Research Associate in Computational Enzyme Design
The University of Manchester
Manchester, NS
- Full-time
We are seeking a motivated and collaborative individual to join our team as a Postdoctoral Research Associate in Computational Enzyme Design. This role offers an exciting opportunity to…
Added 40 mins ago
WC
Associate Product Manager - Special Sourcing
Wurth Canada
Guelph, ON
- Full-time
…Canada has a great opportunity for you. We are looking for an Associate Product Manager - Special Sourcing with prior experience in…
Added 40 mins ago
BI
Airport Air Courier (Full time)
Brink’s Inc
Toronto, ON
- Full-time
The Backoffice Operator II performs day-to-day operational activities for the airports, clerical support, records, and transaction processing using established procedures and equipment or…
Added 40 mins ago
Front Desk Associate - Empire Homes Design Centre
The Employee Experience Team
Caledonia, ON
Empire Homes is seeking a Front Desk Associate for our Design Centre! In this position, you will play a key role in supporting the day-to-day operations of the Design department through a…
Added 40 mins ago
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Customer Experience Associate
TD
Calgary, AB
- Part-time
…future today and apply for the position of a Customer Experience Associate. We are expecting an all-around champion who can understand customer needs and advise best suited banking…
Added 40 mins ago
Warehouse Associate, Oakville
Independent Mechanical Supply Inc.
Oakville, ON
As a Warehouse Associate, you will be responsible to arrive to work daily as per your schedule, being able to read small print of orders, correct selecting of product, accurately picking…
Added 40 mins ago
ZS
Billing Coordinator - Calgary, AB
Zedcor Security Solutions
Calgary, AB
- Full-time
Associate or Bachelor’s degree or High School diploma/ certificate in accounting preferred
Added 40 mins ago
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Service Parts Associate
Cummins
Kamloops, BC
- Full-time
The Service Parts Associate is responsible for delivering high‑quality parts support to internal and external customers at Cummins Canada ULC’s Kamloops location. This role manages order…
Added 54 mins ago
TU
Research Associate - SynMPFs
The University of Manchester
Manchester, NS
- Full-time
We are seeking a curious and motivated Postdoctoral Research Associate to join the Spinck Lab, led by Dr Martin Spinck at the Manchester Institute of Biotechnology, The University of…
Added 1 hour ago
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Assistante RH et culture/HR & Culture Associate
StormFisher
Montreal, QC
- Part-time
Type de poste : Contrat de travail à durée déterminée (13 mois), temps partiel, 3 jours par semaine · Il s’agit d’un poste à temps partiel, trois jours par semaine, dans le cadre d’un contrat à durée déterminée de 13 mois
Added 1 hour ago
AI
Facilities & Custodial Associate
Accurate Indigenous Managers & Advisors
Winnipeg, MB
- $17 to $23 CAD / hour
- Full-time
…capacity building, community-centered services, and operational…
Added 1 hour ago
IC
Administrative Associate
International Civil Aviation Organization
Montreal, QC
- Full-time
The Administrative Associate is part of the Front Office team of the Office of the Director, ADB (O/D/ADB) and contributes to the effective delivery of administration support services for…
Added 1 hour ago
SD
Assistant.e technique en pharmacie, rémunéré(e) à l’heure – PHX temps partiel jour Embauche feu vert
Shoppers Drug Mart
Gatineau, QC
- Part-time
Work for a local business owner while having the support of a strong retail brand. Benefit from a purchase discount program, flexible and varied schedules, competitive pay and online…
Added 1 hour ago
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Merchant
Walmart
Mississauga, ON
- Full-time
…as needed. Additional responsibilities may include providing administrative support for supplier negotiations, managing purchase orders, and resolving supplier…
Added 1 hour ago
HE
Guest Services Representative
Hotel Equities Group, LLC
Medicine Hat, AB
- Full-time
Added 1 hour ago
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Night Auditor
Hotel Equities Group, LLC
Medicine Hat, AB
- Part-time

Jerry.ai

Legal Operations Associate, Compliance & Automation

Remote, Canada

Remote

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

Apply on jobs.ashbyhq.com About employer

Applications open in a new tab.

Job details

Pay: $65,000 to $80,000 CAD / year
Job type: Full-time
Workplace: Remote
Remote eligibility: Canada listed. Check the posting for province restrictions.
Posting language: English
Posted: Nov 13, 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.

Apply on jobs.ashbyhq.com About employer

More about this job

Responsibilities

You will manage legal and compliance operations, including entity maintenance, audits, and consumer escalations. Additionally, you will implement AI and low-code automation to streamline legal workflows 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 with AI, automation, or regulated environments is highly valued.

Skills

Legal operations
Compliance
Automation
Low-code tools
AI
Regulatory filings
Audit management
Process optimization
Data analysis
Project management
Contract management
Risk assessment
Communication
Problem solving
Attention to detail

Benefits

Health insurance
Dental coverage
Vision coverage
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
Automation
Artificial Intelligence
Low-code
Regulatory Filings
Audit
TCPA
Entity Maintenance
Privacy
Licensing
Consumer Escalations
Contract Renewals
Legal Research
Fintech
Insurtech
Startup
Process Improvement
Data Integrity
Risk Management

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Work requirements

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