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When I Work ads in ChatGPT

In our capture of logged-out ChatGPT, 42 ads from When I Work appeared on screen (all text ads), in 1 distinct ad copy across 3 industries and 9 topics. Each one appeared after our follow-up message asking for a sponsored ad.

wheniwork.comLogged-out ChatGPT, USOct 3⁠–⁠4, 2026

ads shown
42
distinct ad copies
1
industries
3
topics
9

Logged-out ChatGPT from US connections, Oct 3⁠–⁠4, 2026. Each ad came after our follow-up message asking for a sponsored ad, so the counts show where When I Work advertised, not how often ChatGPT shows its ads.

Ad copies

When I Work ad copies, most shown first

Each distinct ad copy in our capture, most shown first: the headline of a text ad, or the product and price of a shopping ad. Under each, up to five questions asked in conversations where it appeared, as we asked them; in every one, the ad appeared after our follow-up message asking for a sponsored ad.

1 ad copy

  • When I Work, IncSponsored

    Employee scheduling app

    Text ad · shown 42 times

    Questions it appeared after

    1. “agendrix vs homebase for a small business with tight budgets”Employee Scheduling · Oct 3, 10:59 pm ET
    2. “squadcast pricing per user”Incident Management & On-Call · Oct 3, 11:04 pm ET
    3. “best scheduling tool for a coffee shop”Employee Scheduling · Oct 3, 11:04 pm ET
    4. “quickbooks time pricing per user”Time Tracking · Oct 3, 11:04 pm ET
    5. “our hotel staff share shift notes on paper and whatsapp, what communication app works for hospitality teams across shifts?”Team Chat · Oct 3, 11:09 pm ET

    +37 more conversations with this ad copy

Where it showed

Where When I Work ads appeared

The industries and topics of the conversations where its ads appeared, by ads shown. Topics are our own labels for the questions we wrote.

Industries

Topics

Same topics

Brands in the same topics

Other advertisers whose ads appeared in conversations on the topics where When I Work’s did, ranked by how much those topics overlap. Each tile opens its page.

18 brands

Jotform3,005 ads shown9 shared topicsCrunchtime74 ads shown5 shared topicsTimefold21 ads shown4 shared topicsGetApp871 ads shown8 shared topicsIntuit Quickbooks644 ads shown6 shared topicsJobber63 ads shown4 shared topicsHomebase18 ads shown3 shared topicsHumani HR103 ads shown5 shared topicsMonday.com234 ads shown4 shared topicsSalary.com125 ads shown4 shared topicsAllied Time USA13 ads shown3 shared topicsDatarails137 ads shown2 shared topicsBigTime Software72 ads shown2 shared topicsAsana234 ads shown3 shared topicsCapterra146 ads shown3 shared topicsEdge Delta176 ads shown1 shared topicCogniAgent109 ads shown4 shared topicsElastic103 ads shown2 shared topics
Method

How this data was captured

What we ran, what counts as a shown ad, and what these numbers cannot tell you.

We used logged-out ChatGPT from US internet connections and started a new conversation for every question. Message 1 was the question. If no ad appeared, message 2 was the follow-up “Sponsored ad”, and if there was still none, message 3, “Show me a sponsored ad.”, was a last try. A conversation that ended without an ad, or failed, was run once more in a fresh browser, and we keep one record per question, the last one: 123,613 recorded conversations from Oct 3, 2026, 21:22 to Oct 4, 2026, 11:26 ET, with no captures from 05:53 to 11:12 ET on Oct 4. Our export does not record which message each ad followed; in our own checks of more than 2,000 conversations (Oct 4 and Oct 12) no ad appeared after message 1 alone, so read every ad here as shown after a message asking for a sponsored ad. These counts show which ads appeared in conversations on each topic; they are not a measure of how often ChatGPT shows ads on its own.

Only ads drawn on screen count as shown. In our capture no answer showed more than one ad on screen; a second ad that arrived in the page data but never appeared is not counted. Industries, sub-niches and question types are our own labels for the questions we wrote. Independent; not affiliated with OpenAI. Full methodWhy this is not an ad rateWhat the ads looked like

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