Certified Appraiser, Property Tax Appeals — Florida (Contract)

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 rule