Why We Exist

Your car and your home are your most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey – insurance, repairs, financing, maintenance – is fragmented, complicated, and expensive. Jerry is building the first app to manage it all.

We started with car insurance in 2019, became one of the top three brokers in the country, then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, scaled revenue 70X, and became profitable in early 2024.

Why We're Hiring

The next frontier is helping people with the cost of owning a home. Property tax appeals is one of the first offerings we're building – and the Florida appeals season is starting.

This is a domain where being 90% right isn’t going to cut it. Florida's Value Adjustment Board process has a 25-day filing window, a partial-payment requirement that silently kills otherwise-valid petitions, and 67 counties that each run the process differently. Before a single homeowner's petition depends on what we build, we need someone who has lived inside that system to pressure-test it.

This is a deliberately narrow engagement – a few hours a week from someone excellent. The work is advisory: reviewing what we build, flagging what won't survive contact with the VAB, and telling us when we're wrong before it costs a customer.

Why You Will (Or Won't) Like Working Here

Hourly, as-needed: This is an independent contractor engagement at roughly 5–10 hours per week with no fixed schedule. If this product starts to see traction, there is a path to a full-time permanent role if you’re interested.
Early-stage product: You are advising on a new product. The customer flows, backend authorization flows, and filing logic is still being shaped. Your job is to help guide our design and help correct things before we push it to production.

What You'll Own

Regulatory grounding: Clarify how things like Chapter 194, F.S. and the DOR uniform rules (12D-9, 12D-10) operate in practice and not only how they read on paper.
County-level reality: Walk us through how the Property Appraiser's offices and VABs actually differ across the volume counties: Miami-Dade, Broward, Palm Beach, Hillsborough, Orange, Duval, Pinellas, and Lee.
Filing mechanics: TRIM notice timing, the 25-day window, DR-486 and its variants, e-filing versus paper, and the §194.014 partial-payment requirement – guide us through the process.
Hearings and evidence: Help build a flow that actually wins in front of a special magistrate – comparable selection, the 15-day and 7-day evidence exchange windows, and condition-based arguments.

Who You Are

Built inside the VAB system: You can describe why Broward is different from Hillsborough without looking it up. Your knowledge was built through filings or arguing petitions, not advising on property tax from a distance.
Volume-tested: You've worked across hundreds of parcels and seen enough edge cases that you recognize the pattern before it becomes a problem.
Procedurally sharp: You know every step of the appeals process as if it was the back of your hand.

What You'll Bring

5+ years of direct, hands-on Florida experience filing residential property tax appeals.
Personal experience filing or arguing petitions before a Florida VAB, or adjudicating them as a special magistrate.
No active conflict: not currently advising another company building consumer property tax appeal software.
Florida-based strongly preferred, given county-level familiarity requirements.

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

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.

Originally posted on Himalayas

Property Tax Advisor — Florida (Contract)

Job Description