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Added 1 min ago
UO
Senior Advisor, Research Chairs
University of Ottawa
Ottawa, ON · Tabaret Hall
- Full-time
…Research Chairs Programs. Provides expert high-level advice to the leadership team within the Office of the Vice-President, Research and Innovation (OVPRI) to support strategy and decision…
Added 16 mins ago
MC
Procurement and Contracts Specialist
Medical Council of Canada
Ottawa, ON
- $86,000 to $97,000 CAD / year
- Contract
You’ll be immersed in a collaborative and inclusive work environment that fosters professional development and work-life balance.
Added 16 mins ago
D
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…
Added 16 mins ago
C
Mobile Mortgage Advisor (Cobourg/Peterborough/Belleville, ON) - 100% Commission
CIBC
Belleville, ON · Cobourg, ON · Peterborough, ON · Toronto, ON
- Full-time
…clients achieve their home ownership dreams. As a Mobile Mortgage Advisor, you’ll have the flexibility to meet with your clients where and when it’s convenient for them. You’ll make lasting…
Added 16 mins ago
C
Associate Financial Advisor
CIBC
Prince George, BC
- Full-time
…difference in our clients' lives. As an Associate Financial Advisor, you’ll form a deep understanding of your personal and small business clients’ needs as you recommend simple,…
Added 16 mins ago
C
Associate Financial Advisor
CIBC
Victoria, BC
- Full-time
…difference in our clients' lives. As an Associate Financial Advisor, you’ll form a deep understanding of your personal and small business clients’ needs as you recommend simple,…
Added 16 mins ago
B
Senior Business Development Manager
BMO
Toronto, ON · BMOPLACE
- Full-time
Boldly Grow the Good in Business and Life - Become BMO's next Senior Business Development Manager supporting BrokerEdge clients in making real financial progress. Situated in Toronto…
Added 16 mins ago
B
Manager, AML FIU
BMO
Toronto, ON · YNG
- Full-time
Attracts, retains, and enables the career development of top talent.
Added 16 mins ago
B
Senior Manager, First Party Fraud Analytics - Lending
BMO
Toronto, ON · FCP
- Full-time
…analytical strategies, drive innovation, and serve as a trusted advisor on emerging fraud trends, analytics best practices, and the application of data-driven insights to protect the bank…
Added 16 mins ago
B
Senior Manager, First Party Fraud Analytics - Onboarding
BMO
Toronto, ON · FCP
- Full-time
…analytical strategies, drive innovation, and serve as a trusted advisor on emerging fraud trends, analytics best practices, and the application of data-driven insights to protect the bank…
Added 16 mins ago
B
Senior Manager, First Party Fraud Analytics - Cards
BMO
Toronto, ON · FCP
- Full-time
…analytical strategies, drive innovation, and serve as a trusted advisor on emerging fraud trends, analytics best practices, and the application of data-driven insights to protect the bank…
Added 16 mins ago
B
Senior Manager, First Party Fraud Analytics - Business Banking
BMO
Toronto, ON · FCP
- Full-time
…analytical strategies, drive innovation, and serve as a trusted advisor on emerging fraud trends, analytics best practices, and the application of data-driven insights to protect the bank…
Added 16 mins ago
B
Business Development Manager
BMO
Toronto, ON · BMOPLACE
- Full-time
Boldly Grow the Good in Business and Life - Become BMO's next Business Development Manager supporting BrokerEdge clients in making real financial progress. Situated in the Greater Toronto…
Added 31 mins ago
M
Manager, Consumer Insolvency
MNP
Ottawa, ON
- Full-time
…financial challenges and achieving financial freedom. As a trusted advisor, you’ll help individuals and organizations recover from times of financial distress and regain control of their…
Added 31 mins ago
M
Senior Manager, Assurance and Accounting - Audit
MNP
Vancouver, BC
- Full-time
…evolving business and financial reporting landscape. As a trusted advisor, you’ll provide comprehensive, tailored financial information that enables clients to make informed decisions with…
Added 46 mins ago
OM
Business and Fiscal Planning Advisor
Ontario Ministry of Transportation/ Ministère des Transports de l’Ontario
ON · Ontario, Canada
- $80,089 to $115,402 CAD / year
- Full-time
As a Business and Fiscal Planning Advisor, you will:
Added 46 mins ago
CP
Shareholder Intelligence Analyst
Carson Proxy Advisors
Toronto, ON
- Contract
· Monitor relevant shareholder activity, activist developments, proxy advisor guidance and governance trends that may affect client objectives or campaign strategy.
Added 46 mins ago
UO
Senior Advisor, Research Chairs
University of Ottawa
Ottawa, ON
- Full-time
…Research Chairs Programs. Provides expert high-level advice to the leadership team within the Office of the Vice-President, Research and Innovation (OVPRI) to support strategy and decision…
Added 46 mins ago
T
Total Rewards Manager
TEEMA
Toronto, ON
- $110,000 to $120,000 CAD / year
- Full-time
The successful candidate will work closely with senior leadership, Finance, and People & Culture partners to ensure total rewards programs remain competitive, equitable, compliant, and…
Added 46 mins ago
BH
IT Advisor (Cybersecurity Risk Advisor)
BC Hydro
Vancouver, BC
- $109,700 to $138,700 CAD / year
- Full-time
Reporting to the Technology Cybersecurity Manager, the IT Advisor will conduct cybersecurity security reviews, risk, and compliance activities within the Technology KBU.
Added 46 mins ago
FG
Associate Director, Full-Stack Applications - Credit Module
Fitch Group
Toronto, ON
- $150,000 to $170,000 CAD / year
Join our fast‑growing Toronto hub, where we’re using AI to reshape global credit decisions and the software development lifecycle. Here you’ll help us modernize and reinvent our…
Added 46 mins ago
S
Manager, Internal Controls - CA
Stantec
Edmonton, AB
- Full-time
Manage Internal Controls processes and priorities while serving as a trusted advisor to senior leadership, providing practical guidance on complex financial reporting and control matters…
Added 46 mins ago
MF
Director, Citizen Development & Employee Technology Experience Pod Owner
Mackenzie Financial Corporation
Toronto, ON · Greater Toronto Area, ON
- Other
Provide day-to-day leadership, coaching and feedback to pod team members; partner with Product and Delivery Chapters on standards, capability development, staffing and best practices.
Added 1 hour ago
DC
Electrical Engineer
Dillon Consulting Limited
Chatham-Kent, ON · Guelph, ON · Hamilton, ON · Kingston, ON · Kitchener, ON · London, ON · Oakville, ON · Ottawa, ON · Toronto, ON · Vaughan, ON · Windsor, ON · Chatham, ON
- Full-time
Are you someone with strong leadership and technical capabilities? Do you enjoy building relationships and working collaboratively in a team environment with both internal and external…
Added 1 hour ago
DC
Electrical Engineer
Dillon Consulting Limited
Windsor, ON
- Full-time
Are you someone with strong leadership and technical capabilities? Do you enjoy building relationships and working collaboratively in a team environment with both internal and external…

Jerry.ai

Associate Counsel (Remote)

Remote, Canada

Remote

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

Apply About employer

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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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