No, think it through.
Poster said, "I've contributed to keeping prisoners in prison."
This is in no way an inherently good thing--especially given the well-documented clusterfuck that is the judicial system in the US. Have you ever been through the wringer?
I don't think that kudos for helping that system is in order, unless it was specifically something like "I wrote software to help schedule inmate times so that violent offenders and trouble inmates were not put in the same areas at the same time as nonviolent or well-behaved inmates."
As for the second point--look, it's insurance claims. Depending on what the poster did, this ranges from "I helped people get the best claims service from their provider" to "I helped the provider service the bare minimum number of claims." Without more information on what was done, that topic has a lot of room for bad.
"Fix the base system" would be something like "I made a simpler marketplace so that care providers (doctors) can directly bill patients, cheaply and transparently."