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Added 1 hour ago
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Fellowship and Bursary Administrative Assistant
RI-MUHC | Research Institute of the MUHC | #rimuhc
Montreal, QC
- Full-time
Do you want to work for a world-renowned research institute that pushes the boundaries of biomedical science and health research? Right here in Montreal! At the Research Institute of the…
Added 1 hour ago
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Research Associate
RI-MUHC | Research Institute of the MUHC | #rimuhc
Montreal, QC
- Full-time
The MyeliNeuroGene Research Laboratory, directed by Dr. Genevieve Bernard, MD, MSc, a clinician-scientist, is looking for a motivated person to fill the position of full-time Research…
Added 1 hour ago
SZ
Commercial Litigation Lawyer
Spetter Zeitz Klaiman PC
Toronto, ON
- Full-time
Spetter Zeitz Klaiman (SZK) has an exciting opportunity for a mid-level associate (3+years) with demonstrated experience in commercial litigation to join our busy and expanding litigation…
Added 1 hour ago
Associate, New Verticals - Canada
DoorDash Canada
Vancouver, BC · Toronto, ON
We are hiring an Associate onto our New Verticals Strategy & Operations team to grow our Grocery, Convenience, Alcohol and Retail businesses across Canada. About half of your time will…
Added 2 hours ago
CW
Business Development Specialist, full-time position
City Wide Facility Solutions
Burnaby, BC
- $43,000 to $55,000 CAD / year
- Full-time
Find and research businesses that would benefit from City Wide's services
Added 2 hours ago
CW
Business Development Specialist, full-time position
City Wide Facility Solutions
Vancouver, BC
- $43,000 to $55,000 CAD / year
- Full-time
Find and research businesses that would benefit from City Wide's services
Added 2 hours ago
OW
Oliver Wyman- Private Capital/Industrials- Senior Consultant/Associate
Oliver Wyman Group
Toronto, ON
- Other
Knowledge and in-depth experience with customer research techniques (interviews, surveys, focus groups, etc.).
Added 3 hours ago
SI
Senior Customer Growth Marketing Specialist, Staples Promotional Products
Staples Inc.
Vaughan, ON
- Full-time
Conduct in-depth customer and industry research to develop tailored marketing strategies and recommendations.
Added 3 hours ago
AA
Project Management Analyst
August Advisors
Toronto, ON · Greater Toronto Area, Canada
- Full-time
Reporting to the Associate, the responsibilities of the Analyst will include, but are not limited to:
Added 3 hours ago
EI
Test Specialist - CDU
Ecolab Inc.
Calgary, AB
- Full-time
Added 4 hours ago
Marketing Specialist, Events/Spécialiste du marketing, événements
Make-A-Wish Canada / Rêves d'enfants Canada
Montreal, QC
-Dr. Jeremy Friedman, Associate Paediatrician-in-Chief, SickKids Hospital & Medical Advisor for Make-A-Wish® Canada
Added 4 hours ago
Marketing Specialist, Events
Make-A-Wish Canada / Rêves d'enfants Canada
Montreal, QC
-Dr. Jeremy Friedman, Associate Paediatrician-in-Chief, SickKids Hospital & Medical Advisor for Make-A-Wish® Canada
Added 4 hours ago
PC
Corporate Finance Senior Associate (Bilingual FR/EN)
PwC Canada
QC · Clarke City, QC
- Full-time
As a Corporate Finance Senior Associate (Bilingual FR/EN) , you’ll work as part of a team of problem solvers, helping to solve business issues, deliver high-quality client service and…
Added 5 hours ago
UO
Student Associate - WS
University of Cincinnati
Clermont, QC
- Full-time
Founded in 1819, the University of Cincinnati ranks among the nation’s best urban public research universities. Home to more than 53,600 students, 12,000 faculty and staff, and over 360,000…
Added 5 hours ago
UO
Student Associate
University of Cincinnati
Clermont, QC
- Part-time
Founded in 1819, the University of Cincinnati ranks among the nation’s best urban public research universities. Home to more than 53,600 students, 12,000 faculty and staff, and over 360,000…
Added 5 hours ago
R
Revenue Management Associate
RevWhisper
Hamilton, ON
- $52,000 to $70,000 CAD / year
- Full-time
Use internal analytics, AI, and MCP-connected tools to analyze data and support decisions; own the research, recommendations, and execution.
Added 6 hours ago
CM
Media Associate, Investment
Critical Mass
Toronto, ON
- Full-time
As an Associate Media Planner, you are eager to dive into the world of media trafficking, reporting and implementation, and hit the ground running with support from the Media team. With…
Added 6 hours ago
PC
Corporate Finance Senior Associate (Bilingual FR/EN)
PwC Canada
Quebec, QC
- Full-time
As a Corporate Finance Senior Associate (Bilingual FR/EN) , you’ll work as part of a team of problem solvers, helping to solve business issues, deliver high-quality client service and…
Added 6 hours ago
SI
Litigation Associate Lawyer
Synectics Inc.
Lethbridge, AB
- Full-time
Seeking a Litigation Associate with 2-5 years of experience to join a growing litigation practice in Lethbridge, Alberta. The role offers immediate file carriage, independent case…
Added 6 hours ago
CB
Accounts Payable Clerk (Contract)
Clark Builders
Edmonton, AB
- Full-time
Tax: Prepare and review of tax returns, assist in tax compliance and reporting, research, and document retention.
Added 6 hours ago
UO
Communications & PR Specialist
University of Niagara Falls Canada
Niagara Falls, ON
- $65,000 to $75,000 CAD / year
- Full-time
…including overseeing all communications projects as assigned by the Associate Director of…
Added 6 hours ago
FP
Shipping and Freight Associate
Fresh Prep 🇨🇦
Victoria, BC
- $22 CAD / hour
- Part-time
Research shows that while men apply to jobs when they meet an average of 60% of the criteria, women and other marginalized folks tend to only apply when they check every box. So if you…
Added 6 hours ago
FR
Marketing Research Coordinator
FirstService Residential Canada
Mississauga, ON
- Full-time
Our dedication to associate satisfaction and growth is recognized by our Great Place to Work certification, exemplifying our commitment to fostering a positive and inclusive workplace…
Added 6 hours ago
A
Clinical Research Associate II (GTA)
AbbVie
Oakville, ON
- $81,000 to $131,000 CAD / year
- Full-time
…Monitoring Plans, and to quality standards in conducting clinical…
Added 7 hours ago
UO
Post Doctoral Associate, Immunology, DNA damage, and Apoptosis
University of Calgary
Calgary, AB
- Full-time
…University of Calgary, is seeking a highly motivated Postdoctoral Associate with strong expertise in immunology, DNA damage, and apoptosis biology. The research program focuses on…

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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