> 1) an 8-person company will be a shit-show and not a good experience for my first adventure in start-up world, especially coming from a large legacy insurance company

There is a lot to be learned from shit-shows and even sinking ships and the experience can be invaluable to your career.

> 2) sales in start-ups is easily the least defensible position - not as "valuable" as engineering and product.

If you are confident in your ability to this shouldn't truly be an issue. Sales is also often a crucial piece to a startup that is often overlooked and ripe with opportunity for the right people.

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I'm not sure what exactly you are looking for here. Only you will be able to make this decision. Neither is wrong and it sounds like you may just be seeking validation. Regardless, don't look back too hard and with much regret no matter your choice.

I'd personally make the decision based on the people that I'd be working with and my interest in the work/sector. Even the perfect position can suck if you dislike the people that you work with or don't believe in the product.