I dont think we have seen the category killer yet.
Lemonade has some potential but we (or at least I) dont have any real info to evaluate what it is they are doing. Just something employing P2P & behavioral economics. I can see them adding new data points into the actuarial / underwriting process, but then they will have to get that approved by each state's office of insurance regulators. They are the first mover, but they have a lot of moving to do.
On the Data / IOT front, I am not as up to date on the players, but someone will take the lead and get acquired in the next 2-3 years, is my guess. What lasting change that will bring to the industry is a question in my mind. You have Google who now own's Nest, has eyeballed the Insurance industry, and knows Data pretty well. I would not be surprised to see them come up with their own offering, and maybe even capitalize their own carrier to support the Data venture.
I am rather pessimistic on any business without any core business model evolution. For example, on the idea of Just In Time Coverage, simply selling monthly/weekly/daily policies instead of annual does not excite me. Rather selling by the Mile/Kilometer is mildly more interesting, but still does not exhibit a departure from the core set Insurance Functions, just a new pricing model.
I am really not sure we have seen the first big winner yet. We may see some nice several hundred million plus acquisitions in the next couple of years, but I think those will be looked at in hindsight as having been overvalued.
I think simply operating the function set of an Insurance Company (as embodied in the Industrial age) will become more & more of a loss leader service, it will need to be coupled with some additional offerings to make any money.