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I don't think they anonymize the search, they just send it directly to Bing or Google. Anonymizing the search wouldn't earn them any money.

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They kind of do. They are a proxy service, so your IP and browsers are hidden I assume. The search results are coming from Bing and Google.

How does it earn them any money to begin with? I know the article claimed they have a revenue of $250 million a year, but unless they are somehow injecting their own ads, how does a simple redirection result in any revenue for them?

They do inject their own ads

> [...] a search for “airpods” on Bing leads to a Search Encrypt search results page that has more ads than search results. A user would have to have the stamina to scroll through 10 text ads from Microsoft and then 5 image ads before coming to an organic search result

So is there an ad bidding system and marketplace they run with a separate user interface that requires ad buyers to login and purchase ads?

They use Bing for their search results and ads. Microsoft does all the work to onboard advertisers.

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