I think the best way to make a difference with software would be as a consultant, deploying with units and doing work straight from there, in an ad-hoc way. Similarly I guess to the stories about how the Obama elections team worked. Deploying a small group of devs with a battle group, who have for purpose to write custom software to make the battle group more efficient. By participating in the pre-deployment training and exercise, the devs could familiarize themselves with the most important tools that need to be created for the deployment. Then while deployed, polish the rough edges and adapt the tools to new situations.

Otherwise, going through the procurement chain of the army will inevitably lead to insanity and bad software, and no actionable result. We had software when I went about writing those tools; it was just so bad and inappropriate that nobody used it.