I think he meant
"hold it against" as in "hold it next to" to cross-check both NLT and the other translations.
He likes to refer to both NLT and other versions.
Here against does not mean "opposing" which is what leads to the confusion I think
The expression "a kick in the ass" (or, more mildly, "a kick in the pants") is sometimes used to refer to jumpstarting an individual, or getting a situation back on the right track, as in:
"Our son needs to get a job!"
"Yes, he needs a good kick in the pants."
It stands to reason, then, that "boot" can be substituted for "kick," since that's the net result, when the one doing the kicking happens to be wearing boots.
He himself felt sorry for the people who were in horrible pain, but some need the good boot in the ass. (J.E. Jackson, Camp Pain: Talking With Chronic Pain Patients, 1999).
If you want, check out this Ngram. You can see that all these phrases are used, but kick in the pants seems to be most common.
Your example usage:
Does Google need a strong engineer to put a boot in the ass to develop the next XXX ...
reads a little awkward, since it's usually an outsider, or one with some authority, doing the kicking, and it's hard to tell whose butt is going to be kicked in that sentence. (Google's?) If the "strong engineer" is in charge of a group of engineers who are developing XXX, then the expression might work, but I'd probably write more like this:
Google needs a strong engineer to put a boot in the ass of the team developing the next XXX ...
Best Answer
What you describe is not an idiom as such, although it does make use of an idiom.
"to pit (something) against (something)" means to place the two things in opposition or competition against each other. This usage is a standard idiom.
"to pit (something) against (something) technically" is not an idiom. It's just extending the meaning into a technical area. The meaning is to place the two things in opposition or competition against each other on a technical basis.
Also, note that you have placed "technically" in the wrong place in your question. In English we don't put the adverb like "technically" in between the main verb "pit" and the direct object "something". You need to put the adverb before or after the verb and objects. That is, "to pit sth. against sth. technically", or potentially "to technically pit sth. against sth".
EDIT: In a comment below, the questioner gives another example:
This is just the standard idiom "to pit (something) against (something)", although I think you may be analyzing it incorrectly. In this case we should analyze it as:
...where the first "something" is "technically accomplished X", or an X that has shown technical accomplishments, and the second "something" is "Y".