Legal Operations Associate (Remote)

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 http://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.

Jerry operates across the US and Canada, and our legal team keeps all of it running: entity filings, IP protection, compliance audits, consumer escalations, regulatory changes, and the systems behind them. The team is small, so this role comes with real scope early. You’ll own Jerry’s legal and compliance operations: make sure recurring work is done right, run the programs that need judgment, and keep rebuilding them with AI and low-code tools, so a small team can do the work of a much larger one.

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

WHY YOU WILL (OR WON’T) LIKE WORKING HERE

• Real ownership early: You report directly to our Legal Counsel and work closely with them across the team’s full scope. You’ll own a set of compliance programs for the long term, and you’ll be the first point of contact for teammates who run day-to-day compliance work.

• Room to build: Many of our legal processes are still being optimized. You’ll decide how they should work and build the systems behind them.

• Building and operating: Alongside the building, a large share of the job is recurring work: filings, deadlines, audits, complaint responses, and quality checks that have to be done exactly right, every time. Your accuracy keeps Jerry in good standing in every jurisdiction, and people who enjoy both sides of the role do well here.

• Growth that tracks results: You’ll learn from leaders who come from Amazon, Better, LinkedIn, McKinsey, BCG, and Bain. Promotion is based on performance and ownership alone, so strong work moves you forward fast.

WHAT YOU’LL OWN

• Compliance operations: Run, review, and quality-check the recurring compliance work, including entity maintenance, privacy requests, and licensing support.

• Marketing compliance and audits: Run TCPA and Do Not Call audits, monitor opt-outs, and keep marketing guidelines current. Check the accuracy of AI-powered audits, and design new audit programs with sampling plans and scoring rubrics.

• Consumer escalations: Investigate complex escalations to their root cause, work with Product, Operations, and Engineering on the fix, and turn recurring issues into compliance training for teams across the company.

• Regulatory change and readiness: Track regulatory changes, along with issues surfaced by complaints and audits, and see each one through to action. Keep Jerry ready to answer regulator inquiries, carrier audits, and partner diligence quickly.

• Legal team support: Support contract renewals, legal research, and product reviews with intake, fact gathering, trackers, and follow-up.

• Automation and AI: Replace manual legal tasks with AI and low-code workflows, and own the reliability of every script, report, and AI tool the team depends on.

WHO YOU ARE

• A Closer: You track every open item until it’s done, and you find the answer yourself before asking someone else for it.

• A Builder: The second time you do a task by hand, you start working out how to automate the third. You reach for a spreadsheet or a low-code tool before a manual checklist.

• A Zero-Error Operator: Regulatory filings and audits leave no room for mistakes, and you work accordingly. You keep your own system so no deadline or cross-functional project slips.

• A Root-Cause Investigator: You don’t stop at the symptom. You dig into the records, find what actually went wrong, and follow the fix through until it’s done.

• A Proactive Communicator: You provide updates without being chased, flag blockers early, and make sure teammates know what happens next.

• Comfortable with ambiguity: You can take an unclear brief, define the problem yourself, and move on it with urgency. You also know which calls to make yourself and which to escalate.

WHAT YOU’LL BRING

• A Bachelor’s degree from an academically rigorous program, with a record of high performance.

• A track record of owning projects start to finish and solving problems without being told how, at school, at work, or on your own.

• Hands-on experience using AI and technology to improve how work gets done, such as a tool, automation, or process you built yourself, and the habit of checking AI output before relying on it.

• Experience in compliance, legal operations, audit, or another regulated environment is a plus, but not required.

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 http://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 a