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Added 3 mins ago
BB
Retail Financing and Sales Associate (Seasonal)
Best Buy Canada
St. John's, NL
- Part-time
Join our team! We are hiring immediately for a retail financing and sales associate, which we call a financing advisor at Best Buy. As a retail financing and sales associate, you will help…
Added 32 mins ago
M
Senior Delivery Lead, Strategic Accounts
Monks
Toronto, ON
- Full-time
In this Senior Delivery Lead, Strategic Accounts – Programmatic role, you will serve as a strategic advisor and primary point of contact for a portfolio of large, complex clients. You'll…
Added 32 mins ago
EJ
Associate Analyst - Financial Planning
Edward Jones
Mississauga, ON
- $77,000 to $127,000 CAD / year
- Full-time
The Canada Financial Planning team is seeking an Associate Analyst to support the development, maintenance, and delivery of financial planning advice and guidance for our Canadian business.…
Added 2 hours ago
Bilingual Wish Discovery Coordinator (12-month contract)/Coordonnateur.trice, exploration des rêves (contrat 12 mois)
Make-A-Wish Canada / Rêves d'enfants Canada
Montreal, QC
Added 2 hours ago
Customer Accounts Advisor
Talent Acquisition/Human Resources, The Aaron's Family of Companies
Prince Albert, SK
…are 100% satisfied with their product. As a Customer Accounts Advisor, you will build relationships with our customers over the phone and face-to-face to bring them one step closer to…
Added 2 hours ago
Bilingual Wish Discovery Coordinator (12-month contract)
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 2 hours ago
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Client Service Associate, Private Wealth
BMO
Toronto, ON · FCP
- Full-time
As a Client Service Associate with BMO Nesbitt Burns, you’ll be an integral part of an Investment Advisor team, helping deliver a high-quality wealth management experience to clients.
Added 2 hours ago
ScotiaMcLeod Business Development Associate
Scotiabank
Vancouver, BC
As a Business Development Associate, you will work with an Advisor to support growth through prospecting and developing new client relationships.
Added 2 hours ago
RU
Tax Senior Associate - Private Company
RSM US LLP
Toronto, ON
- Full-time
RSM’s Private Company practice is looking for a dynamic Tax Senior Associate to join our team. At RSM, our Private Company practice is rooted in strong relationships based on a deep…
Added 3 hours ago
TT
Senior Category Management Specialist
The TJX Companies, Inc.
Mississauga, ON · CAN Home Office Mississauga ON
- $76,620 to $107,268 CAD / year
- Full-time
Enjoy Associate discounts at our stores, available to you and eligible family members.
Added 3 hours ago
Investment Associate (Contract position)
The Canada Life Assurance Company
Winnipeg, MB
The Investment Associate plays a key supporting role in delivering a high-quality advisory and investment experience to high-net-worth clients. Working closely with Investment Counsellors,…
Added 3 hours ago
Senior Advisor Associate
The Canada Life Assurance Company
ON · Mississauga Ontario, ON
Our IPC Securities Operations team is currently growing! We are seeking a Senior Advisor Associate – someone who can provide exceptional client service and support to our Advisory teams to…
Added 4 hours ago
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Business Solutions Advisor
Nulogy
Remote, Canada
- Full-time
- Remote
…to join our growing marketing team as a Business Development Associate (BDA). Reporting to a BDR, this role provides an exciting entry point into the world of sales and marketing within a…
Added 4 hours ago
EI
Brand Protection Advisor
Ecolab Inc.
Moncton, NB · Halifax, NS
- Full-time
Ecolab is seeking a Brand Protection Advisor to join its EcoSure division, an industry leader in food safety and total quality assurance. Our specialists are valued food safety & QA…
Added 4 hours ago
MS
Client Success Manager, Associate (Canadian Public)
Morgan Stanley
Calgary, AB
- Full-time
Interface with client contacts, financial advisor team, service center, and internal operations
Added 5 hours ago
PA
Pre-Owned Automotive Sales Representative
Pfaff Automotive Partners Inc.
Markham, ON
- Full-time
Key Words: Automotive Sales Representative, Auto Sales Consultant, Product Advisor, Vehicle Sales Consultant, Car Sales Representative, Sales Associate, Automotive Retail Sales, Sales…
Added 5 hours ago
RJ
Corporate Actions Associate
Raymond James Ltd.
Vancouver, BC
- Full-time
The position of Corporate Actions Associate requires the ability to effectively balance varied functions, while maintaining our high level of service and attention to detail. Proven…
Added 5 hours ago
RJ
Mutual Funds Associate
Raymond James Ltd.
Vancouver, BC
- Contract
The Mutual Funds Associate will be responsible for supporting the Systematic Plans and Non-Financial Updates functions within the department. Responsibilities will include reviewing and…
Added 6 hours ago
W
Administrative Associate (LeBlanc Family Wealth)
Wellington-Altus
Kingston, ON
- Full-time
Provide information, where requested and approved by an Associate or Advisor, on the status of a client’s account and provide account balances, quotes and other marketing information.
Added 6 hours ago
J
Legal Operations Associate (Remote)
Jerry.ai
Remote, Canada
- $65,000 to $80,000 USD / year
- Full-time
- Remote
Added 8 hours ago
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Operations Associate
Wellington-Altus
Winnipeg, MB
- Full-time
Provide timely and accurate responses to documentation queries and account opening requests from internal departments and investment advisor teams.
Added 9 hours ago
C
Product Safety / Occupational Health Safety Coordinator
Collabera
Brampton, ON
- $26 to $27 CAD / hour
- Contract
Serve as a trusted safety advisor and advocate for associate wellbeing, building strong partnerships across all levels of the organization.
Added 12 hours ago
NB
Technology Associate
National Bank of Canada
Winnipeg, MB
- Full-time
A career as an Associate at National Bank is a role where your systems thinking, attention to detail, and interest in finance can have a direct impact on clients and advisors. In this role,…
Added 17 hours ago
UO
Undergraduate Advisor and Coordinator
University of Waterloo
Stratford, ON · Digital Media Stratford
- Full-time
The Undergraduate Advisor and Coordinator plays a key role in supporting undergraduate students in the Faculty of Arts. The Advisor provides academic advising, supports student engagement…
Added 22 hours ago
A&
Associate, Restructuring
Alvarez & Marsal
Toronto, ON
- Full-time
As a Restructuring & Turnaround Associate, you will have the opportunity to work alongside professionals recognized as authorities across a diverse set of industries, and with the guidance…

Jerry.ai

Legal Operations Associate (Remote)

Remote, Canada

Remote

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

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Job details

Pay: $65,000 to $80,000 USD / 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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