The software products we have at Health Solutions are functional just the technology and the platforms they run on are very outdated. If we could bring back the product leadership innovators we laid off and get rid of this power hungry has been leadership, we may could modernize. Our present Health Solutions leadership thinks 40 year old software products are marketable. The current leaders choose the people to be laid off to protect their jobs. This cycle will have to end if we are to get anywhere.
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It's a tough problem, shared by just about every company out there. $Millions and $millions invested in these legacy apps. OP says "modernize" and there are a few paths available; from "re-hosting" to re-writing, Gartner will tell them all about the options for a fee. And guess what? None of them are cheap or will give them what they have today in terms of functionality, features, and reliability (relative low level of defects ie think you got bugs now? just try a rewrite!)
What it comes down to, any modernization effort, at whatever level, are huge projects, butts in seats, long, ie expensive! Stoneman ain't got no time for that! Hell, he cut $350 million in staff since he's owned the company.
Sales has to sell what they have, it's not legacy, it's battle tested, it's not outdated, it's feature complete, it's not ugly, it's efficient for users.
The challenge for the c-suite is to get out of this box. Just about every company out there fails at this. There is one example I think has merit, it's what Cisco has done on a couple of occassions. Give some motivated talented employees some cash to do a start up in the same domain, give them an ownership stake and let them do the innovation. Then when they've got tranction in the market, absorb them back in. The layoffs and toxicity drove off anyone who'd be capable of that though.