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Added 28 mins ago
KD
Key Account Manager - Metro
Keurig Dr Pepper
Mississauga, ON
- $86,200 to $115,000 CAD / year
- Full-time
Work closely with the internal cross functional (Partner/Brand/Omni) teams in aligning and executing promotional plans and strategies.
Added 28 mins ago
A
Senior Compensation Specialist
ATB
Remote, Canada
- Full-time
- Remote
As ATB’s next Senior Compensation Specialist, you won’t just be evaluating numbers - you’ll be helping to shape the total reward strategies that motivate our people and drive business…
Added 28 mins ago
T
Personal Banking Associate Trainee (Mandarin or Cantonese Language Skills an asset)
TD
Richmond, BC
- Full-time
…refer customers to the appropriate team member or internal Bank partner, while ensuring a positive customer…
Added 28 mins ago
T
Customer Experience Associate - Spanish Language Skills an Asset
TD
Burnaby, BC
- Part-time
Our Total Rewards package reflects the investments we make in our colleagues to help them and their families achieve their financial, physical, and mental well-being goals. Total Rewards at…
Added 28 mins ago
U
Specialty Support Representative III
UKG
Montreal, QC
- Full-time
Added 28 mins ago
SC
district manager, North York, ON
Starbucks Coffee Company
Toronto, ON
- $84,300 to $111,250 CAD / year
- Full-time
Our Total Rewards package is built to support your growth, wellbeing, and sense of belonging. Here’s a look at what eligible partners can expect, visit starbucksbenefits.ca for details.
Added 28 mins ago
Assistant Manager
EssilorLuxottica Group
Ottawa, ON
Total Rewards: Benefits/Incentive Information
Added 1 hour ago
A
Director, Business Development – Construction (Canada)
Acciona
Mississauga, ON · CAN - Mississauga Office
- Full-time
In addition to base salary, this role includes a total rewards package that supports employee well-being, development, and long-term growth, subject to company policies and applicable…
Added 1 hour ago
T
Personal Banking Associate - O'Brien, Ville Saint Laurent (Part-time, 18.75h/week)
TD
Montreal, QC
- Part-time
Our Total Rewards package reflects the investments we make in our colleagues to help them and their families achieve their financial, physical, and mental well-being goals. Total Rewards at…
Added 1 hour ago
T
Personal Banking Associate Trainee (Full time)- St-Sauveur
TD
Saint-Sauveur, QC
- Full-time
…refer customers to the appropriate team member or internal Bank partner, while ensuring a positive customer…
Added 1 hour ago
T
Personal Banking Associate Trainee - Mandarin or Cantonese Language Skills
TD
Richmond, BC
- Full-time
…refer customers to the appropriate team member or internal Bank partner, while ensuring a positive customer…
Added 1 hour ago
S
Software Engineering Manager, Enterprise
Spellbook
Remote, Canada
- Full-time
- Remote
…funding, led by Keith Rabois at Khosla Ventures, bringing its total funding to more than $80…
Added 2 hours ago
PB
Risk & Compliance Analyst / Auditor
Pacific Blue Cross
Burnaby, BC
- Full-time
Partner with leaders and business teams, bringing together risk, compliance, audit, and operational perspectives to provide practical insights and recommendations that support effective…
Added 2 hours ago
OB
Branch Manager, Kelowna
Odlum Brown Limited
Kelowna, BC
- Full-time
…rewarding team members and do this by providing a competitive total rewards package that is fair and equitable; mentorship programs; and a variety of professional development opportunities…
Added 2 hours ago
T
Personal Banking Associate - Robert-Bourassa Branch, Montreal
TD
Montreal, QC
- Full-time
Our Total Rewards package reflects the investments we make in our colleagues to help them and their families achieve their financial, physical, and mental well-being goals. Total Rewards at…
Added 2 hours ago
T
Customer Experience Associate
TD
Regina, SK
- Part-time
Our Total Rewards package reflects the investments we make in our colleagues to help them and their families achieve their financial, physical, and mental well-being goals. Total Rewards at…
Added 2 hours ago
T
Manager, Customer Experience
TD
Thunder Bay, ON
- Full-time
Our Total Rewards package reflects the investments we make in our colleagues to help them and their families achieve their financial, physical, and mental well-being goals. Total Rewards at…
Added 2 hours ago
MS
Sales Manager
Michaels Stores
Stoney Creek, NB
- Full-time
Promote and enroll customers in the Loyalty Rewards Program, driving retention and repeat visits through consistent execution.
Added 2 hours ago
CC
Industrial Automation Specialist
Colas Canada Inc.
Toronto, ON · North York, ON
- Full-time
We offer a competitive total rewards package, including:
Added 2 hours ago
BI
Bilingual BMO Insurance Service Centre Analyst
BMO Insurance
Toronto, ON
- Full-time
Added 2 hours ago
J
Sales Strategy & Operations Manager
Jobber
AB · Edmonton, AB
- Full-time
…Sales Operations Manager, you’ll act as the Sales Operations partner for an assigned channel or priority area of focus, helping identify operational friction and turn business problems into…
Added 2 hours ago
L
Community Specialist | Tanger Outlets Ottawa
lululemon
Ottawa, ON
- Full-time
Establish and manage local key relationships (e.g., Ambassadors, Sweat Collective, studio owners, lululemon Studio partner studios) to increase new guest acquisition and guest retention.
Added 2 hours ago
L
Educator TEMPS-PLEIN | Carrefour Laval
lululemon
Laval, QC
- Full-time
Added 2 hours ago
C
Senior Application Security Developer
Clio
Calgary, AB · Vancouver, BC · Toronto, ON
- Full-time
…automate vulnerability discovery, drive automated remediation, and partner with product teams across…
Added 2 hours ago
AG
Director, Growth & Innovation Operations
Altus Group
Toronto, ON
- Full-time
● Bring innovation into everyday operations. You will partner with Product, Engineering, and business teams to evaluate and advance technology, automation, and AI-enabled opportunities. You…

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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