[Hiring] Legal Operations Associate @Jerry.ai

Role 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.

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
• 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
• Keep rebuilding them with AI and low-code tools

The person who succeeds in this role is a natural driver:

• Owns their work from start to finish
• Solves complex problems without a manual
• Has the grit to thrive in a startup environment

Qualifications

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

Requirements

• Run, review, and quality-check the recurring compliance work, including entity maintenance, privacy requests, and licensing support
• Run TCPA and Do Not Call audits, monitor opt-outs, and keep marketing guidelines current
• Investigate complex escalations to their root cause
• Track regulatory changes and see each one through to action
• Support contract renewals, legal research, and product reviews
• Replace manual legal tasks with AI and low-code workflows

Benefits

• Health, dental, and vision coverage
• Paid time off
• Paid parental leave
• 401(K) plan with employer matching
• Wellness benefits
• Equity opportunities may also be part of your total rewards package

Company Description

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.

Imagine having a trusted friend in your pocket who takes care of everything:

• Finds you the right car or home at the right price
• Locks in the best insurance rate without you lifting a finger
• Reminds you before that service appointment turns into an expensive repair
• Helps you sell at the best price when the time is right

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.