One of my relatives very close to me is VP of sales and ops at a Fortune 250 B2B insurance co. You definitely hit the nail on the head with #2. On another not

One of my relatives very close to me is VP of sales and ops at a Fortune 250 B2B insurance co. You definitely hit the nail on the head with #2. On another note, One of my good friends started working as a direct sales rep for the same company selling group insurance to very small businesses(5-20 people). He has tons of sales experience...But four months in is still stumbling and struggling with how complicated their products(plans) are...and he is one of the top people in their new batch of sales reps. It is a complicated industry, but a lot of the complications shouldn't have to involve the actual customers or product. Unfortunately the complications they build into product can help make them a lot of money. If you want to go after this market. Take an approach like Square. Hide all of the necessary complications(regulations, etct) of the industry so the customers don't even have to be aware or think about them. Then start off by gaining a foothold in an under served and less profitable market segment like small biz group insurance (guys selling couch on craigslist and farmers market vendors ~= 1-10 employee small biz in insurance). Then start building from there