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Added 2 mins ago
Advisor Associate - Hamilton
Scotiabank
Hamilton, ON
The Associate contributes to the overall success of the Client Administrative Services Regional team, ensuring specific individual goals, plans, initiatives are executed / delivered in…
Added 2 mins ago
Customer Experience Associate - Orillia Branch (22.5 Hours/Week)
Scotiabank
Orillia, ON
As a Customer Experience Associate, you are the face, character and heart of our branches. Scotiabank is a place where we put our customers first, and our priority is to help them achieve…
Added 2 mins ago
ScotiaMcLeod Administrative Associate
Scotiabank
White Rock, BC
As an Administrative Associate you will work closely with a Wealth Advisor in the development and management of their book of business by providing effective client service and contributing…
Added 2 mins ago
TP
Institutional Client Service Associate
TDS Personnel
Toronto, ON
- Contract
Our client, a leading global investment management firm, is seeking an Institutional Client Service Associate to join their Toronto team on a six-month contract basis. In this entry-level…
Added 17 mins ago
MI
Senior Associate Director, Fund Accounting
MUFG Investor Services
Halifax, NS
- Full-time
Added 17 mins ago
EB
Associate Director, Internal Audit AML/ATF/SE
EQ Bank
Toronto, ON
- Full-time
The Associate Director, Internal Audit will be responsible for leading the risk assessment, control identification, documentation, testing, findings and recommendation process for various…
Added 32 mins ago
T
Personal Banking Associate Trainee
TD
Red Deer, AB
- Full-time
…with their financial needs? We are seeking a Personal Banking Associate Trainee for our branch office who can guide customers to the appropriate staff member for resolving their financial…
Added 32 mins ago
T
Customer Experience Associate
TD
Drayton Valley, AB
- Part-time
…future today and apply for the position of a Customer Experience Associate. We are expecting an all-around champion who can understand customer needs and advise best suited banking…
Added 32 mins ago
T
Customer Experience Associate
TD
Brampton, ON
- Part-time
…future today and apply for the position of a Customer Experience Associate. We are expecting an all-around champion who can understand customer needs and advise best suited banking…
Added 32 mins ago
T
Customer Experience Associate
TD
Brampton, ON
- Part-time
…future today and apply for the position of a Customer Experience Associate. We are expecting an all-around champion who can understand customer needs and advise best suited banking…
Added 32 mins ago
T
Customer Experience Associate - Sherbrooke, King Ouest (Part-time, 15h/week)
TD
Sherbrooke, QC
- Part-time
Added 32 mins ago
T
Customer Experience Associate
TD
Brampton, ON
- Part-time
…future today and apply for the position of a Customer Experience Associate. We are expecting an all-around champion who can understand customer needs and advise best suited banking…
Added 32 mins ago
T
Personal Banking Associate - Prince-Arthur (15 hours)
TD
Montreal, QC
- Part-time
…with their financial needs? We are seeking a Personal Banking Associate for our branch office who can guide customers to the appropriate staff member for resolving their financial queries…
Added 32 mins ago
MD
Chief Operations Officer - Core Operations Director
Minnesota Direct Care and Treatment
Saint-Paul, NB · St.-Paul, NB
- Full-time
Added 32 mins ago
RI
Senior Investor Relations Associate
Romspen Investment Corporation
Toronto, ON
- Full-time
The Senior Investor Relations Associate is a key member of our Investor Relations team, responsible for providing exceptional service to our investors. This role involves managing investor…
Added 47 mins ago
B
Sourcing Associate, Human Resources Category
BMO
Toronto, ON · YNG
- Full-time
…Benefits, Recruitment, Relocation and Training, the Sourcing Associate leads sourcing activities and negotiations, acts as a trusted advisor to stakeholders on project deliverables,…
Added 47 mins ago
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Associate, Commercial Banking (Public Sector Group)
BMO
Toronto, ON · FCP
- Full-time
The Associate, Public Sector is a unique career opportunity in commercial banking to work on large complex transactions with a high performing team while serving large public sector…
Added 47 mins ago
Senior Customer Experience Associate - Rockland, On (15h/week)
Scotiabank
Clarence-Rockland, ON · Rockland, ON
Added 47 mins ago
HI
Administrative Associate
HUB International
Edmonton, AB
- Full-time
As an Administrative Associate, you will be the first point of contact for everyone who walks through our doors or calls our office. This is a role for someone who takes pride in keeping…
Added 1 hour ago
ST
Manager, Investor Services
SS&C Technologies
Toronto, ON
- Full-time
Managing daily responsibilities of Associate and Senior Associates, Associate Managers including involvement in their development and performance.
Added 1 hour ago
ST
Manager, Investor Services
SS&C Technologies
Mississauga, ON · Toronto, ON
- Full-time
Managing daily responsibilities of Associate and Senior Associates, Associate Managers including involvement in their development and performance.
Added 1 hour ago
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Personal Banking Associate
BMO
Burnaby, BC
- Full-time
Added 1 hour ago
Financial Service Representative
Money Mart
Waterloo, ON
Added 1 hour ago
MI
Senior Associate Director, Fund Accounting
MUFG Investor Services
Halifax, NS
- Full-time
Added 1 hour ago
Customer Support Associate (PS)
British Columbia Lottery Corporation
Vancouver, BC

Jerry.ai

Associate Counsel (Remote)

Remote, Canada

Remote

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

Apply About employer

Applications open in a new tab.

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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