I don't think it's effective. I thought it was pretty stupid. In my opinion, it makes the women look (1) too dumb to understand that context can make a difference (which I think it does for at least some of those quotes), and (2) incredibly weak/too sensitive since they're indelibly hurt by these words. (I voted for waste of time.)
ETA: I just read that blog post you cited and agree. This part rang true to me: "But on the 3D level of persuasion, what the viewer sees is several average-looking women in bad moods complaining about a guy being, well… a guy." Watching it actually sort of reminded me of when ladies get together and one's going through something bad with a guy, and everyone says reassuring platitudes, like, "guys are jerks" or "mean" or "stupid" or "forgetful" or whatever. I would expect a political leader to be more cautious about what they say publicly, but we all know that Trump is a businessman and entertainer first. In the end, this ad almost makes Trump's statements seem more any-guy than offensive.