She doesn't want to spend $400 on buying a new version of Premier and HR has more important things to anyway than to redo it
Are you kidding me? Your company is crippled with old software because you guys want to avoid a $400 expense? Holy hell.
Remember the goal of business is to raise the share price.
Yeah, and nothing causes share prices to skyrocket like saying we don't want to spend $400 to get rid of old, outdated, depricated, insecure, buggy, vulnerable, easily-exploitable software.
Wait you don't use flash or old java at work? Wow, no cisco or vsphere at all.
We dumped Cisco years ago, good riddance. We're only 2 servers away from cutting ties with Microsoft as well, and we only build training using Flash if the customer specifically requires it, otherwise it's done in HTML 5. And, no, we do not use Java for anything. I've instructed people to make sure Java is off their machine.
You know what else we don't use? IE8, IE6, or Flash 11. We don't even test on IE8 any more, we have language in our contracts which say that if customers find bugs in their training which are only present in IE8, and they want those bugs fixed, they need to pay to have them fixed. We no longer provide free support for IE8, and no one cares. Our customers know they need to upgrade, instead of paying to fix bugs that only affect them they find it a better use of their time and money to update their software and other materials. Most companies find that to be a necessary and useful expense, in fact.
I notice that you didn't address the "impossible" nature of replacing your software. It's obviously possible, modernizing your company is clearly possible and one day will be necessary, you just have no desire to actually do it. Don't make it sound like you have no choice, you guys are just lazy. This is what happens when you have a CFO determining IT policy instead of a CTO, but I'm guessing you don't want to pay a CTO either. Those shareholders each need their additional penny that a competent CTO would cost the company, right?