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Added 18 mins ago
Automotive Sales Advisor - Campus Honda Victoria
The Jim Pattison Auto Group
Victoria, BC
…individual to join our Campus Honda Victoria sales team as a Sales Advisor. If you strive to achieve excellence in customer satisfaction and relationship building, this opportunity is for…
Added 18 mins ago
K
Consultant, Financial Services-Insurance & Wealth & Asset Management
KPMG
ON · Toronto, Ontario
- Full-time
KPMG’s Management Consulting practice is growing its Strategy & Operations team focused on insurance and wealth management. We are looking for Consultants who want to help leading financial…
Added 18 mins ago
K
Manager, Financial Services-Wealth & Asset Management
KPMG
ON · Toronto, Ontario
- Full-time
Developing as a trusted advisor within Financial Services, with a focus on Wealth and Asset Management and related sectors.
Added 18 mins ago
T
Project Advisor, Digital Printing -Markham, ON
TPH
Markham, ON
- Full-time
The purpose of the Project Advisor role is to assist the Manager in immediately responding to the volume of inquiries by consulting on Customer requests, making recommendations and then…
Added 1 hour ago
J
Legal Researcher (Remote)
Jerry.ai
Remote, Canada
- $80,000 to $110,000 CAD / year
- Full-time
- Remote
Strong organization and project-management skills, with the ability to manage multiple matters and deadlines at once.
Added 1 hour ago
J
Operations Associate (Legal & Compliance)
Jerry.ai
Remote, Canada
- $65,000 to $80,000 CAD / year
- Full-time
- Remote
Added 2 hours ago
DB
Part Time Bridal Sales
David's Bridal
Hamilton, ON
- Part-time
…them and taking care of them with one of the highest customer service scores in…
Added 2 hours ago
K
Senior Tax Manager, Asset Management
KPMG
ON · Toronto, Ontario
- Full-time
Our Asset Management Tax practice continues to grow, and this opportunity offers a senior‑level role supporting complex investment fund clients across their full tax life cycle. As a Senior…
Added 2 hours ago
BE
Mechanic - Shop Foreman
Battlefield Equipment Rentals
Timmins, ON
- Full-time
…mechanics, we want to hear from you. As a key member of the Service team, the Mechanic Shop Foreman plays a vital role in keeping our rental fleet and customer equipment operating safely,…
Added 2 hours ago
BE
Mechanic - Shop Lead
Battlefield Equipment Rentals
Sudbury, ON
- Full-time
…mechanics, we want to hear from you. As a key member of the Service team, the Lead Heavy Equipment Mechanic plays a vital role in keeping our rental fleet and customer equipment operating…
Added 2 hours ago
Senior Strategist, Enterprise
BrainStation
Toronto, ON
Act as a trusted advisor to your clients, leading them through opportunity discovery and managing the day-to-day relationship across the life of an engagement
Added 2 hours ago
Manager, Enterprise
BrainStation
Toronto, ON
Serve as the senior day-to-day advisor to your clients, leading them through opportunity discovery, managing expectations and stakeholders, and ensuring each engagement delivers measurable…
Added 2 hours ago
Advisor, Strategic Procurement
Regional Municipality of Wood Buffalo
Fort McMurray, AB
From IT and Accounting to Asset Management and Taxation, our Corporate Services Division supports the entire municipality. This division ensures we remain fiscally responsible,…
Added 2 hours ago
B
Construction administrator
BPA
Toronto, ON · Greater Toronto Area, Canada
- Full-time
Support project delivery strategies and risk management initiatives.
Added 3 hours ago
DB
Part Time Bridal Sales
David's Bridal
Dartmouth, NS
- Part-time
…them and taking care of them with one of the highest customer service scores in…
Added 3 hours ago
DB
Part Time Bridal Sales
David's Bridal
Woodbridge, ON
- Part-time
…them and taking care of them with one of the highest customer service scores in…
Added 3 hours ago
K
Senior Consultant, Financial Services-Insurance & Wealth & Asset Management
KPMG
ON · Toronto, Ontario
- Full-time
KPMG’s Management Consulting practice is growing its Strategy & Operations team focused on insurance and wealth management. We are looking for Senior Consultants who want to help leading…
Added 3 hours ago
TW
Business Advisor, Agriculture
Thrive Wealth Management
Humboldt No. 370, SK · Prince Albert, SK · Humboldt, SK
- Full-time
…providing creative solutions to come on board as a Business Advisor, Agriculture to assist our members in Humboldt and area. The preferred locations for this position are Humboldt and…
Added 3 hours ago
TW
Financial Advisor
Thrive Wealth Management
Saskatoon, SK
- Full-time
As a full-time, temporary Financial Advisor in Saskatoon, SK at our Eighth branch, with an end date February 2028, you are responsible for understanding our members’ financial goals and…
Added 3 hours ago
VF
Assistant Branch Manager
Valley First
Enderby, BC
- $64,400 to $82,500 CAD / year
- Full-time
The ABM is responsible for the leadership of an assigned team of branch advisory employees (up to the Financial Advisor position) and ensures current and potential members receive…
Added 4 hours ago
B
Manager, Wealth Reporting Analytics & Automation
BMO
Toronto, ON
- Full-time
…on the configuration, applicability, and usability of data management, data analytics, and data visualization solutions to support these…
Added 4 hours ago
M
Advisor, Rapid Transit Analysis
Metrolinx
Canada
- Full-time
Our Rapid Transit Insights team is currently seeking an Advisor for a 18 months contract role to join their team. Reporting to the Manager, Rapid Transit Insights, the Advisor will carry…
Added 6 hours ago
RA
Senior Legal Advisor - Expert Witness Services
Ridge and Partners LLP
London, ON · Bristol-London, ON
- Part-time
Contribute to the management, governance and continued development of our Expert Witness practice.
Added 7 hours ago
NO
SENIOR ADVISOR, STRATEGIC AND DIGITAL COMMUNICATIONS
NFB ONF Education
Montreal, QC
- Full-time
…events. Monitors the audiovisual environment, advises executive management, coordinates digital initiatives, and evaluates the impact of strategies to maximize the NFB's…
Added 8 hours ago
NN
Supply Planner
Nestlé Nespresso SA
Montreal, QC
- Full-time
…portfolio. This role is critical in enabling high customer service levels by having optimized inventory, while minimizing distribution costs. Acting as a subject matter expert for the…

Jerry.ai

Operations Associate (Legal & Compliance)

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 2, 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, product reviews, consumer escalations, and audits. The team is small, so this role comes with real scope early. You’ll run core legal operations and rebuild 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 a project 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. The projects you take on are yours from start to finish.
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, and audits 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

Automation: Use AI and low-code tools to replace manual legal tasks with workflows that run on their own.
Legal and regulatory projects: Work with our Legal Counsel on legal research, contract reviews, and other substantive projects as new questions come up.
Entity compliance: Keep Jerry’s corporate entities in good standing across the US and Canada, handling annual reports and state requests end to end on your own.
Brand protection: Monitor Jerry’s intellectual property, find infringements, and initiate cease-and-desist workflows.
Consumer escalations: Investigate complex escalations to their root cause, recommend fixes, and turn recurring issues into compliance training for teams across the company.
Product compliance reviews: Review products and processes for compliance risk and user friction, then work with Engineering and Product to fix the underlying issue.
Compliance audits: Lead audits across operations and keep watch on the highest-risk areas between them.

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 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.

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.
Demonstrated interest in using AI and technology to improve how work gets done, such as a tool, automation, or process you built yourself.

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 core legal operations, including entity compliance, brand protection, and regulatory filings, while leveraging AI and low-code tools to automate manual workflows. Additionally, you will conduct legal research, perform contract reviews, and investigate consumer escalations to improve overall compliance and product processes.

Requirements

The role requires a Bachelor's degree from an academically rigorous program and a proven track record of owning projects from start to finish. Candidates must demonstrate strong problem-solving skills, high attention to detail, and a proactive interest in using technology and AI to improve operational efficiency.

Skills

Legal operations
Compliance
Automation
Low-code tools
Legal research
Contract review
Entity compliance
Brand protection
Consumer escalations
Regulatory filings
Project management
Data analysis
Process optimization
Communication
Problem solving
Attention to detail

Benefits

Health insurance
Dental insurance
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
Compliance
Operations
Automation
AI
Low-code
Regulatory
Entity filings
Intellectual property
Contract review
Startup
Fintech
Insurtech
Risk management
Audits
Project ownership
Process improvement
Data-driven
Cross-functional collaboration
Corporate governance

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