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Added 4 mins ago
D
Product Owner, Product Management
Desjardins
Levis, QC · Montreal, QC
- Full-time
As Product Owner, Product management, you will represent the voice of the client in projects and be responsible for the member/client experience. You will consistently prepare a range of…
Added 4 mins ago
PM
Director of Finance
Pulse Medica
Edmonton, AB
- Full-time
…forecasting, cash management, fundraising support, investor readiness, and strategic financial analysis. The successful candidate will serve as a trusted business partner to the CEO and…
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Personal Finance Advisor
Desjardins
Lorrainville, QC · Montreal, QC · Notre-Dame-du-Nord, QC · Témiscaming, QC · Caisse Desjardins du Témiscamingue
- Full-time
As a personal finance advisor, you’re responsible for developing and maintaining lasting and trusting business relationships with members and clients, to ensure they’re satisfied. Your role…
Added 4 mins ago
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Sourcing Manager, Marketing Category
BMO
Toronto, ON · YNG
- Full-time
This role acts as a trusted sourcing advisor to assigned business groups, helping stakeholders evaluate sourcing alternatives, supplier capabilities, commercial models, market conditions,…
Added 4 mins ago
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Sourcing Associate, Human Resources Category
BMO
Toronto, ON · YNG
- Full-time
HR category or HR services sourcing experience, including recruitment, learning and development, compensation and benefits, or HR technology, is an asset.
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Senior Financial Advisor - Elliot Lake, ON
Scotiabank
Elliot Lake, ON
At Scotiabank we help employees build their futures – where they can be themselves, and win together. With a commitment to diversity and inclusion and a performance-oriented culture that…
Added 4 mins ago
Senior Financial Advisor - Downtown Halifax, Nova Scotia (Future Opportunities)
Scotiabank
Halifax, NS
At Scotiabank we help employees build their futures – where they can be themselves, and win together. With a commitment to diversity and inclusion and a performance-oriented culture that…
Added 4 mins ago
Financial Advisor- Speedvale & Stevenson, Guelph ON
Scotiabank
Guelph, ON
At Scotiabank we help employees build their futures – where they can be themselves, and win together. With a commitment to diversity and inclusion and a performance-oriented culture that…
Added 19 mins ago
D
Product Owner, Product management
Desjardins
Montreal, QC
- Full-time
As Product Owner, you will represent the voice of the client in projects and be responsible for the member/client experience. You will consistently prepare a range of products and services…
Added 19 mins ago
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Commercial Insurance Specialist (T)
Federated Insurance Company of Canada
Mississauga, ON
- Full-time
Are you a natural relationship builder who thrives on winning new business and helping clients succeed? As a Commercial Insurance Sales Agent at Federated Insurance, you'll have the…
Added 49 mins ago
T
PIA Client Service Associate
TD
Markham, ON
- Full-time
…skills, we want to help you succeed. You’ll have regular career, development, and performance conversations with your manager, as well as access to an online learning platform and a variety…
Added 49 mins ago
HR
Spécialiste, Conseiller(ère) Beauté Désigné(e) /Specialist, Designated Beauty Advisor - Tom Ford
Holt Renfrew
Montreal, QC
- Full-time
A job at Holt Renfrew offers a competitive total compensation, a generous employee discount, pension, and health & dental benefits, tuition assistance, and continuous learning and…
Added 49 mins ago
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Senior Advisor, IT Architecture
Desjardins
Levis, QC · Montreal, QC · Complexe Desjardins Montréal
- Full-time
As a Senior Advisor, IT architecture, you actively monitor opportunities offered by new technologies and business approaches for the organization as a whole. You design solutions to meet…
Added 49 mins ago
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People and Culture Business Partner
Progressive
Montreal, QC
- $81,500 to $99,200 USD / year
- Full-time
You'll be the trusted advisor to leaders, the go-to resource for employees, and the Canadian employment law expert helping drive business success while creating an exceptional employee…
Added 49 mins ago
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Advisor
Sun Life Insurance & Investments
Richmond Hill, ON
- Full-time
People from various professional and educational backgrounds have found success in the advisor career at Sun Life. That’s because being a successful advisor is not just about what’s on your…
Added 1 hour ago
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Senior Audit Manager - Capital Markets
BMO
Toronto, ON · FCP
- Full-time
Maintains working knowledge of the industry, regulatory, broad economic environment, and internal environment, as to the development of new strategies and plans, opportunities and risk, to…
Added 1 hour ago
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Senior People Operations (HR) Business Partner
Toronto Blue Jays
Toronto, ON
- Full-time
…building a strong, values-driven culture rooted in collaboration and continuous learning. This on-site role reports to the Director, People…
Added 1 hour ago
NB
Banking Advisor
National Bank of Canada
Kelowna, BC
- Full-time
Our training programs use on-the-job learning to help you master your role. You can access personalized training content on such topics as banking solutions and the advisory approach to…
Added 1 hour ago
NB
Loan Syndication Agency Advisor
National Bank of Canada
Montreal, QC
- Full-time
We favor a variety of forms of continuous learning to enhance your development, including on-the-job learning, training content and working with colleagues with diverse backgrounds and…
Added 1 hour ago
NB
Senior Financial Planning Advisor
National Bank of Canada
Montreal, QC
- Full-time
Bank values continuous learning and internal mobility. Our personalized
Added 1 hour ago
ScotiaMcLeod Senior Financial Planning Associate
Scotiabank
White Rock, BC
Learning and Development – via Scotia Academy, a virtual learning experience to upskill and develop your skills at work or from your personal device
Added 1 hour ago
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Beauty Advisor - Part Time
Sephora
Red Deer, AB
- $17 to $20 CAD / hour
- Part-time
…performance-based bonus opportunities, a competitive benefits program, and robust learning and development initiatives aimed at promoting employee support and…
Added 1 hour ago
S
Paid Services Beauty Advisor - Full Time
Sephora
Milton, ON
- $19.7 to $23.2 CAD / hour
- Full-time
…performance-based bonus opportunities, a competitive benefits program, and robust learning and development initiatives aimed at promoting employee support and…
Added 1 hour ago
Consultant en Déploiement - Apprentissage automatique | Delivery Consultant - Machine Learning, ProServe Shared Delivery Team - Data & AI
Amazon
Calgary, AB · Vancouver, BC · Toronto, ON · Montreal, QC
Are you excited about building software solutions around large, complex Machine Learning (ML) and Artificial Intelligence (AI) systems? Want to help the largest global enterprises derive…
Added 1 hour ago
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Wealth Management Advisor
Desjardins
Châteauguay, QC · Mercier, QC
- Full-time
As a wealth management advisor, you’re responsible for developing and maintaining lasting and trusting business relationships with members and clients, to ensure they’re satisfied. Your…

Jerry.ai

Associate Counsel (Remote)

Remote, Canada

Remote

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

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Job details

Pay: $105,000 to $150,000 USD / year
Job type: Full-time
Workplace: Remote
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 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.

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.

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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 legal escalations, support corporate licensing, 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. A minimum of 2 years of relevant legal experience at a law firm or in-house is required, with strong skills in contract negotiation and legal analysis.

Skills

Contract drafting
Contract negotiation
Regulatory compliance
Legal research
Consumer protection
Privacy law
Insurance law
Risk management
Corporate governance
Legal analysis
Stakeholder management
Policy development
Licensing
Dispute resolution
AI-assisted drafting
Legal writing

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

Associate Counsel
Legal
Commercial Agreements
Regulatory Compliance
Insurance
Fintech
Consumer Protection
Privacy
Contract Negotiation
Risk Management
Corporate Law
AI
Automation
Legal Research
Policy Design
Licensing
In-house Counsel
Law Firm
JD
LLM
Compliance
Business Expansion
Entity Maintenance
Legal Operations
Stakeholder Management

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