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Added 2 mins ago
PT SALES ASSOCIATE - CALL IT SPRING TSAWWASSEN
The Aldo Group Inc / Le Groupe Aldo Inc.
Tsawwassen, BC
Reporting to the Store Manager, the Part-Time Sales Associate at ALDO is all about driving sales while creating a great in-store experience. You bring the energy, the style, and the…
Added 2 mins ago
Financial Service Representative
Money Mart
Dartmouth, NS
At Money Mart, we understand that not every customer fit with-in traditional banking or prime lending models. That’s why our teams look beyond the credit score to provide accessible,…
Added 2 mins ago
SD
Infirmier(ère), rémunéré(e) à l’heure – PHX temps partiel jour Embauche feu vert
Shoppers Drug Mart
Gatineau, QC
- Part-time
Join a locally owned and operated store to help deliver health, beauty and convenience services in your community, and keep the customer at the centre of everything you do.
Added 2 mins ago
SD
Cashier, Hourly Part Time Day Greenlight Requisition
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 2 mins ago
SD
Front Store Supervisor, Hourly Part Time Day
Shoppers Drug Mart
Cornwall, 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 2 mins ago
SD
Merchandiser, Hourly Part Time Day
Shoppers Drug Mart
Cornwall, 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 2 mins ago
SD
Caissier(ère), rémunéré(e) à l’heure – PHX temps partiel Quarts de travail flexibles
Shoppers Drug Mart
Saguenay, QC
- Part-time
Join a locally owned and operated store to help deliver health, beauty and convenience services in your community, and keep the customer at the centre of everything you do.
Added 2 mins ago
SD
Beauty Manager, Hourly Full Time Flexible Shifts
Shoppers Drug Mart
Hamilton, ON
- Full-time
Always put the Customer first and provides superior customer service
Added 2 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 2 mins ago
SD
Beauty Advisor, Contractor Part Time Evening
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 2 mins ago
SD
Pharmacist, Hourly Full Time Flexible Shifts Greenlight Requisition
Shoppers Drug Mart
Belleville, ON
- Full-time
Communicate with other health care professionals within the circle of care to provide customer care
Added 2 mins ago
SD
Merchandiser, Hourly Part Time Day Greenlight Requisition
Shoppers Drug Mart
Kitchener, 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 2 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 2 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 2 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 2 mins ago
SD
Assistant Front Store Manager, Hourly Full Time Flexible Shifts
Shoppers Drug Mart
Toronto, 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 2 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 2 mins ago
SD
Cashier, Hourly Part Time Day Greenlight Requisition
Shoppers Drug Mart
Kitchener, 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 2 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 2 mins ago
SD
Marchandiseur(seuse), rémunéré(e) à l’heure – PHX temps partiel Quarts de travail flexibles Embauche feu vert
Shoppers Drug Mart
Blainville, QC
- Part-time
Join a locally owned and operated store to help deliver health, beauty and convenience services in your community, and keep the customer at the centre of everything you do.
Added 2 mins ago
SD
Merchandiser, Hourly Full Time Flexible Shifts
Shoppers Drug Mart
Yellowknife, NT
- 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 2 mins ago
SD
Merchandiser, Hourly Full Time Flexible Shifts
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 2 mins ago
W
(CAN) Fashion Team Lead
Walmart
Surrey, BC
- Full-time
…associates through teaching and training. Ensures a high level of customer service while ensuring task…
Added 2 mins ago
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PERSONAL BANKING ASSOCIATE
BMO
Winnipeg, MB
- Full-time
Delivers exceptional service to BMO customers and prospects. Identifies customer needs and provides advice and guidance regarding financial solutions that are in the best interests of…
Added 16 mins ago
TH
Replenishment Analyst- 1 Year Contract
The Home Depot
Canada
- Full-time
Achieve in stock and turns targets for each of the categories that are managed by the analyst for domestic, cross border and import products

Jerry.ai

Associate Counsel, Commercial & Regulatory (Growth-stage tech startup)

Remote, Canada

Remote

$105,000 to $150,000 CAD / year · Full-time

Apply on jobs.ashbyhq.com About employer

Applications open in a new tab.

Job details

Pay: $105,000 to $150,000 CAD / year
Job type: Full-time
Workplace: Remote
Remote eligibility: Canada listed. Check the posting for province restrictions.
Experience: 2+ years of relevant legal experience at a law firm and/or in-house, including substantive experience drafting, reviewing, or negotiating commercial agreements.
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.

Operating across the U.S. and Canada brings a steady flow of commercial, regulatory, consumer protection, and product questions. As our Associate Counsel, you’ll report directly to our Legal Counsel and work with teams across Jerry to turn complex legal issues into practical that help the business move forward.

This role is designed for a lawyer with law firm and/or in-house experience who wants broad responsibility in a growing technology company. You’ll draft and negotiate agreements, advise on product and compliance questions, and drive assigned matters from initial assessment through resolution. You’ll develop your own recommendations and manage day-to-day execution, bringing significant decisions and novel or higher-risk issues to our Legal Counsel.

Why You Will (Or Won’t) Like Working Here

Substantive ownership: You’ll manage matters, work directly with business partners, and bring a clear point of view. You’ll need to distinguish the issues that matter from those that can be resolved pragmatically.
Broad exposure: Your work will span contracts, product launches, insurance and consumer regulation, privacy, and disputes. You don’t need to arrive as an expert in every area, but you should enjoy learning unfamiliar subjects and applying sound judgment.
A small team with a hands-on approach: Our legal team is two people today. You’ll work closely with our cofounder and executives on legal issues that shape business decisions, organize your own matters, follow through on implementation, and help with operational details when needed.
Technology as part of the work: We use AI and automation to improve research, drafting, and legal processes. You’ll be expected to use these tools thoughtfully, verify their output, and take responsibility for the quality of your work.
Growth that tracks results: You’ll work with teammates from companies like Nvidia, Amazon, McKinsey, Bain, and BCG. Promotion is based on performance alone, so strong work moves you forward fast.

What You’ll Own

Commercial agreements: Draft, review, and negotiate agreements with carriers, business partners, and vendors. Identify material risks, propose practical terms, and manage negotiations and internal coordination through execution.
Product and regulatory advice: Research federal and state insurance, consumer protection, privacy, and other requirements. Translate your analysis into clear recommendations on new products, customer flows, disclosures, consent, marketing, and operational processes.
Consumer escalations and regulatory matters: Investigate complex complaints and regulatory inquiries, identify relevant facts and legal issues, and prepare proposed responses. Work with Legal and business teams to resolve matters and address recurring causes.
Compliance and risk management: Help design policies, procedures, training, and controls. Review audit findings, identify issues requiring legal judgment, and work with operational owners to implement and track corrective actions.
Licensing and corporate matters: Address substantive questions arising from entity maintenance, licensing, appointments, and business expansion. Work with colleagues handling recurring compliance operations and escalate material risks.
Emerging issues and legal processes: Take on new legal questions as Jerry launches products and enters partnerships. Improve templates, guidance, and workflows so the team can deliver consistent advice efficiently.

Who You Are

Practical and Thoughtful: You develop a recommendation, explain your reasoning clearly, and balance legal risk with business objectives.
An Accountable Owner: You keep matters moving, manage deadlines, and follow issues through implementation. You investigate independently and recognize when to seek input or escalate.
A Clear Communicator: You write concisely, give useful status updates without being chased, flag blockers early, and make the next step clear.
A Zero-Error Operator: You review every contract and filing with total precision, down to defined terms, dates, and cross-references.

What You’ll Bring

A JD or LLM, with a record of high academic performance.
Admission to practice in at least one U.S. state or in Ontario, in good standing.
2+ years of relevant legal experience at a law firm and/or in-house, including substantive experience drafting, reviewing, or negotiating commercial agreements.
Strong legal research, analysis, and writing skills, with the ability to develop practical recommendations on unfamiliar issues.
Experience managing multiple matters and working with business stakeholders to resolve them.
Experience with U.S. legal matters and regulated businesses, insurance, fintech, consumer protection, or privacy is a plus.

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

The Associate Counsel will draft and negotiate commercial agreements while providing legal advice on product launches, regulatory compliance, and consumer protection matters. They will also manage consumer escalations, regulatory inquiries, and help design internal policies to mitigate business risk.

Requirements

Candidates must hold a JD or LLM degree and be admitted to practice in at least one U.S. state or Ontario, Canada. The role requires at least 2 years of relevant legal experience, specifically in drafting and negotiating commercial agreements.

Skills

Commercial agreements
Regulatory compliance
Contract negotiation
Legal research
Consumer protection
Privacy law
Risk management
Product counseling
Legal drafting
Corporate governance
Licensing
Dispute resolution
Policy development
Regulatory inquiries
Stakeholder management

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

Commercial Law
Regulatory Affairs
Fintech
Insurtech
Contract Law
Privacy
Compliance
Risk Management
Legal Counsel
Startup
AI
Automation
Consumer Protection
Corporate Law
Licensing
Policy Design
Legal Operations
Entity Maintenance
Negotiation
Legal Research

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Work requirements

Jobs in Canada