‘An influential seat at the table’: Why Target’s retail media business Roundel is one of the first to test ChatGPT ads

If ChatGPT’s move into advertising is to become a durable feature of its business rather than a short-term experiment, much will hinge on whether those ads can prove they drive real outcomes, not just impressions.

Target wants to be among the first to find out.

The retailer is one of the first wave of brands to start testing ads across ChatGPT’s free and Go tiers — a pilot which began on Feb. 9, having been delayed three days by OpenAI. It is promoting both its own business and select partners from its Roundel retail media network. The placements will align with specific keywords in user prompts, an attempt to mirror the intent-driven logic of search while adapting it to a conversational interface. Target did not share how much these placements cost, but Digiday previously reported that approached advertisers confirmed they had been told that the ads would be priced at $60 per 1,000 views.

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In Graphic Detail: Subscriptions are rising at big news publishers – even as traffic shrinks

After the pandemic-era surge in news publishers’ subscribers, year-over-year gains are harder to come by, pushing publishers to prioritize retention, moving subscribers to higher-priced tiers and bundles, and product expansion.

Digiday analyzed the subscription and paid reader revenue trends among major news publishers that have publicly shared these numbers, including The New York Times, The Wall Street Journal, Bloomberg Media, The Guardian and Daily Mail.

For a bunch, including The New York Times and The Wall Street Journal, growth isn’t just continuing, it’s speeding up, and likewise so is The Guardian’s paid reader contribution model. Meanwhile, Bloomberg’s subscription business shows signs of normalization after a 2024 spike, and Daily Mail is still ramping up its relatively new subscription business, which launched in 2024 in the U.K. and expanded to the U.S. and Canada in February 2025.

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