Banking Technology
You would expect banks would be up to date with technology particularly in the security.
But somehow there are some banks that don't allow special characters in users' passwords. I expect this password limitation to be a result of compatibility issues with legacy systems. Though I must admit more systems are moving towards 2 step authentication, which is always a good thing.
Then, there are bank transfers. Why do they take as long as they do? Sometimes 3-5 days. From I've read it could be due to automated clearinghouse and having the Federal Reserve process the transfers (which supposedly do once a day). There are also discussions whether the banks intentionally take their time in order to float the money and own interest on it. I'm not sure I believe this but who knows at such high amounts of money. With technology, you would think transfer would be almost instant (at most a day).
While I do see banks that I use are improving their websites, there can be so much they can do to improve the user experience especially when presenting benefits and special offers to their customers. And the mobile experience, most of them are awful and not much more useful than the account balance screen on Mint.
And for trades, how can Robinhood offer free trades while other firms charge a couple to several dollars per trade? Is their advice and other services that most props for use worth that much?! Of course, if you have hundreds of thousands with some firms, you can get discounted or maybe even free trades.