Digiday Daily

January 21, 2026

Presented by

OpenAI is set to wade into the advertising business this year, but its move to finally monetize ChatGPT with ad dollars may have come a touch too late.

ChatGPT’s 2022 launch inaugurated the current generative era and made the app a touchstone for the entire sector. But OpenAI’s head start has since been eroded by rivals, the greatest of which has both momentum and experience building ad businesses.

TOP STORY

Generative AI

Bold Call: OpenAI’s ads pivot may come too little, too late

Advertising is coming to ChatGPT, but not fast enough to outrun incumbent platform giants — one in particular.

OTHER THINGS TO KNOW

Even many of the most successful challenger brands are stuck with siloed data and rented identity, lacking the 360-degree customer view they want. Partner insights from Adstra.
The discussion around brand safety and suitability has matured. The industry is now entering a new phase, where brands expect more control, more extensibility into walled gardens and closer accountability to outcomes. Partner insights from Channel Factory.
Autonomous advertising learns continuously, adapts instantly, frees teams from operational drag, unlocks audiences others can’t see and compounds performance over time — extending expertise for performance marketers. Partner insights from Quantcast.

MEDIA & PLATFORMS

AI Revenue Generation

‘A multi-model world’: Microsoft’s CEO says the future of AI is orchestration, not one single model

Microsoft’s CEO just handed ad execs a survival guide for the agentic era.

AI Revenue Generation

OpenAI is hiring engineers, not ad sellers, first to build its ad business

OpenAI is focused on constructing the machine before worrying about selling what comes out of it.

A MESSAGE FROM TDFOUNDATION

First can’t miss digital media event of 2026

Continue to ring in the New Year on Jan. 22 at the TDF Holiday Cocktails Gala, hosted by New York Athletic Club. Come celebrate the TD Foundation’s 2025 successes and discuss how they’ve helped the children and families of wounded warriors and fallen heroes. Tickets are $300 — $200 for young professionals under 30. Join the 20th annual event at 180 Central Park South, New York, NY 10019, and enjoy spectacular views of Central Park.

RSVP Now

PARTNER INSIGHTS FROM BETTERUP

How leaders are managing the new human-agent hybrid workforce

Leaders need new frameworks for handling the human-agent hybrid workforce. This means rethinking foundational assumptions about expertise, collaboration and career development.

Marketing on Platforms

Pinterest CRO Bill Watkins leaves amid reorganization

The move comes just over three weeks before the company reveals its Q4 2025 earnings update on February 12.

PARTNER INSIGHTS FROM TATARI

How brands win on CTV when they pair programmatic and direct buys

Successful brands are pairing the flexibility of programmatic buying with the access to premium ad inventory and consumer data from publisher-direct buys to gain scale, efficiency and full-funnel impact across CTV.