Have you already gone through licensing and credentialing through the Division of Insurances in various states? Or are you just gauging interest at this point before the licensing steps? Asking because there is a whole E&O element on liability for you as the middleman.
The first-customer-requires-coverage thing is the whole sale. Founders treat insurance like they treat security questionnaires: ignore it until a pilot is blocked, then they need a yes yesterday. I've sold through that motion a few times. The CAD-software denial is the same pattern as a form written for a bank. If you can get them covered without making them look like a different company, that's actually the product.
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