Legal Operations Associate (Remote)

Jerry
Chicago, IL

We’d love to hear from you if you like:

  • Making a big impact on day one with a Forbes Top Startup Employer.

  • Working at a startup that has traction: $240M in funding and 60x revenue growth in 5 years.

  • Mentorship from serial entrepreneurs and brilliant leaders who have scaled companies like Amazon, Better, LinkedIn, McKinsey, BCG, Bain

  • Meritocracy: We promote based on performance, ownership, and results, not tenure.

About the Opportunity:

We are looking for a highly resourceful and ambitious Legal Operations Associate to join our lean, fast-paced legal team. This isn't a traditional "administrative" legal role. We are looking for someone with a product-focused mindset who doesn't just follow a process but seeks to automate and scale it.

The person who succeeds in this role is a natural driver: someone who owns a project from start to finish, solves complex problems without a manual, and has the grit to thrive in a startup environment. If you are a new graduate eager to sit at the intersection of law, technology, and AI-driven efficiency, we want to hear from you.

What You'll Do:

  • Own Entity Compliance: You’ll be the point person for keeping our corporate entities in "Good Standing" across the US and Canada. You’ll handle the reports and state requests entirely on your own.

  • Protect the Brand: Monitor our trademark presence and hunt down infringements. You’ll be responsible for drafting and initiating cease-and-desist workflows.

  • Run Tight Audits: Lead our compliance audits for sales calls, marketing opt-outs, and DNC registries. We aim to exceed consumer protection standards, not just meet them.

  • Automate Everything: Use AI and low-code tools to turn manual legal chores into scalable workflows. Your goal is to build systems that do the work for you.

  • Direct VA Operations: Manage our offshore teams (VAs) to ensure our agent licensing and compliance tasks are executed flawlessly.

Requirements:

  • Academic Excellence: A Bachelor’s degree from an academically rigorous program.

  • Driver Mindset: A proven track record of extreme resourcefulness. You are the type of person who finds the answer before asking the question.

  • Product & Tech Savvy: You have an interest in using AI/technology to optimize workflows. You prefer a spreadsheet or an automated tool over a manual checklist.

  • Impeccable Attention to Detail: You have a "zero-error" mentality when it comes to regulatory filings and compliance audits.

  • Thrive in High-Performance Environments: You’re comfortable with ambiguity and speed. You take full ownership of your output.

While we appreciate your interest and application, only applicants under consideration will be contacted.

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 [email protected]

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.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets.

Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all.

We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started.

Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing.

Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.

Compensation Range: $65K - $80K

Posted 2026-02-28

Recommended Jobs

Ambulatory Nurse (N)- Belleville Pulmonary (Belleville)

BJC HealthCare
Belleville, IL

Additional Information About the Role ~40 hours per week ~ Dayshift Monday-Friday ~ Monday-Thursday 8:00am-5:00pm ~ Friday's 8:00am-3:00pm ~ No weekends or holidays! Overview …

View Details
Posted 2026-02-21

CHEF, EXECUTIVE SOUS I

Eurest USA
Chicago, IL

Unidine Salary: $60,000 - $67,000 Think Fresh! Lead with Excellence! An industry leading hospitality food service group, Unidine is driven by its exceptional people sharing their pass…

View Details
Posted 2026-02-28

VP of Compliance TCRS4658

Trade Compliance Recruiting Solutions
Chicago, IL

HIGH-LEVEL OVERVIEW The Vice President of Compliance is responsible for overseeing international trading compliance as well as business process management and corporate compliance, ensuring adhere…

View Details
Posted 2026-02-12

Design Engineer

Associated Metal Forming Technologies
Morton Grove, IL

Position Title: Design Engineer Reports To:               Tooling and Engineering Manager (204) Approved: 7/26/2018 (MR) Summary: The Design Engineer is active in all Pre-Design, Design and…

View Details
Posted 2026-02-06

Sr Veg Mgmt Program Manager

ComEd
Rockford, IL

Who We Are: We're powering a cleaner, brighter future. Exelon is leading the energy transformation, and we're calling all problem solvers, innovators, community builders and change makers. Work wi…

View Details
Posted 2026-02-19

Bartender

Duck Inn Chicago
Chicago, IL

The Duck Inn is seeking a fun and passionate bartender with experience in a chef driven restaurant with an intense beverage program.  Duck Inn is a Neighborhood Gastro-Tavern & Dining Room situated…

View Details
Posted 2026-02-07

Dental Assistant

Arch Dental
Hoffman Estates, IL

Hoffman Estates Dental is seeking a Dental Assistant to join their friendly and professional team! The practice is dedicated to providing a comfortable, patient-focused environment while offering a w…

View Details
Posted 2026-01-19

RN/LPN - Registered Nurse/Licensed Practical Nurse

The Radcliff
Wood Dale, IL

Job Title: Licensed Nurse (LPN or RN) – Senior Living Location: The Radcliff, 276 E. Irving Park Road, Wood Dale, IL, 60191 Job Type: Full-time Shifts Available: Days / Evenings / Weekends / Ho…

View Details
Posted 2026-02-19

Estate Planning Attorney

MBC Talent Connections
Chicago, IL

Estate Planning & Business Attorney Location: Chicago, IL (Hybrid) Schedule: 3 days in office, 2 days remote Billable Requirement: 1,600–1,800 hours annually Position Overvi…

View Details
Posted 2026-01-29

Tool Room Machinist

MacLean-Fogg Company
Savanna, IL

The Tool Room Machinist interprets blueprints, operates and maintains equipment to fabricate, assemble, and repair precision parts which meet specified dimensions and quality standards. Responsible f…

View Details
Posted 2026-01-19