Knowing it probably wouldn't be on YouTube due to copyright restrictions, but looking there first because Hulu and NBC.com are limited to just US IP addresses, I tried to find the old SNL ad parody, "Sam Waterston for Old Glory" because I thought robot insurance would be a good thing to offer @MiracleWhips19 on their post about "Scary Sci-Fi Baddies" (which I would have shared to the ObservationDeck, if they hadn't of put "Groupthink" in the post title and which I would embed below, but comments replying to this post wouldn't make sense on theirs.)
Unfortunately, the Saturday Night Live bit wasn't on YouTube and it doesn't appear to be cut into a clip for Hulu or NBC. (Though there is a re-enactment done by students at the University of North Texas, if anyone is interested or if they don't know what I'm talking about)
Among the YouTube search results, in addition to the re-enactment, I found an endorsement video Sam Waterston did for a group called "Unity08", a group whose website is gone and whose YouTube channel has been silent for years, which advocated a national internet primary to pick a bipartisan presidential candidate in 2008. Apparently, they tagged the video "robot insurance" because it also comes up on a YouTube search without Waterston's name.
ETA: I see from the group's Wikipedia entry, one of the group's major players was Angus King, former governor and current senator from Maine. In my opinion, he would have a pretty good shot at a bipartisan candidacy and it's something I would encourage him to pursue.
I also see that Waterston appeared on O'Reilly and Hardball in his role as spokesperson for the group. Of course now that I've written all this, I actually remember the campaign, but I still don't know what it has to do with "robot insurance", other than attracting clicks.