About Jerry

Jerry.ai is building an AI agent to manage the physical assets people spend the most on — their cars and their homes. We started with car insurance in 2019, grew to 5M+ customers, raised $240M+, and reached profitability in 2024. We've since expanded into home, motorcycle, and RV insurance.

Owning a home has never been more expensive, and insurance is only part of the bill. We're going after the rest of it.

The Role

This contract-based, hourly consulting position is ideal for someone with deep expertise in Florida's property tax appeal system who can serve as a trusted advisor. There is also potential for this opportunity to evolve into a mutually beneficial partnership as we expand our property tax offering.

What You'll Do

As our Property Tax Appeals Consultant, you will support Jerry's team by providing:

• Regulatory insight: Clarifying Florida statutes, administrative rules, and compliance obligations for property tax appeals.

• County-specific knowledge: Advising on local nuances across Florida's counties, with a focus on the major markets.

• Filing processes: Guiding us through the petition filing process, and explaining requirements for online vs. paper submissions.

• Hearing procedures: Sharing best practices on the Value Adjustment Board process, special magistrate hearings, and effective appeal preparation.

Who You Are

You're an ideal fit if you:

• Have direct experience in Florida's property tax appeal system — through your own practice, an established firm, or a government office.

• Possess deep knowledge of county-level procedures, deadlines, and regulations, especially in Florida's largest counties.

• Are an innovative thinker who combines creative problem-solving with a strong commitment to regulatory compliance.

• Are available to consult remotely on an as-needed, hourly basis.

Why This Role Matters

We're on a mission to make ownership more affordable. Property tax is one of the few items where a homeowner can actually push back — if they know how, and if they don't miss the window. Most don't.

Your expertise will play a pivotal role in helping us expand into new states smoothly and responsibly, ensuring we build on a strong, compliant foundation.

This is a flexible, high-impact consulting opportunity to contribute your expertise without requiring a full-time commitment.

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 [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

Your car and your home are your most expensive assets. And for most people, these 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 or, worse, an accident, and help you sell at the best price when the time is right. That friend is Jerry.

Jerry is building the first AI agent to manage all your physical assets. 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 have been profitable since 2024. We're now expanding into home, motorcycle, RV, and beyond.

We’re fully remote with offices in Palo Alto, New York, Chicago, and Toronto.