Specifically Health and P&C lines. Although Health Insurance is starting to see some innovation in the US.
Reasons:
1. Perceived high barrier to entry, yet that isn't the case. 2. Major players are tech dinosaurs at best. 3. Small brokers (potential customers) dominate the landscape. 4. Legislation keeps markets small because there is little in common from one area to the next - everything is niche. 5. SV thinks it's boring, so you don't need to be the second coming of Steve Jobs to be very successful.
Be warned I'm in Canada though, so my knowledge about the US market is limited, and the two countries are very different in the health insurance sector, as you can imagine.
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
http://news.ycombinator.com/item?id=1396541
I'm specifically looking at providing a video-based training service for a very-well-known vendor's product that many companies in this sector use. Not really a technical challenge, more a knowledge transfer challenge.
In my specific case, the choices available are to either go to the vendor and pay more than 100k to get all the training for 10-15 people simultaneously, or to find someone who's been through it already and mind-meld. I've found one other group who is doing something similar to what I'm thinking, but their offering is laughable (machine voiceover!).
I believe I could easily charge 1k-2k per month for site licenses of well constructed materials. Maybe quite a bit more, especially if I offer custom materials for clients. The foundation would be shared across all though.
Medical software (PACS/RIS in radiology primarily; some automated lab and pharmacy experience, medical paging. Limited EHR/EMR experience).
Firearms (retail, wholesale, and manufacturing of small arms)
(plus crypto/security and some datacenter/cloud/etc. stuff, but that's better covered by existing startups)
Unfortunately, like most 'enterprisey' industries, the long sales cycle will eat you alive if you are not well funded.