I started this newsletter mostly to force myself to keep up with all the new AI marketing news. Things are moving fast! I figured other people might want to learn about it too, so here we are. If there are topics or companies you’d like me to cover, please send them over. I’m a team of one person, so I’ll do what I can. If you want to connect, you can find me running the fractional CMO arm of Foxtown Marketing on most days.

Welcome to today's edition of AI Marketing Geek, your daily dose of the latest AI developments, tools, trends, and actionable insights shaping marketing in 2026. As AI shifts from experimental hype to pragmatic, ROI-driven reality, we're seeing agentic AI take center stage. Autonomous agents are handling media buying, personalization, and commerce, which is wild to watch.

Story 1: ChatGPT Ads Hit $100 Million in Six Weeks. The Self-Serve Era Opens in April.

The number that dropped Thursday on Reuters changes the conversation about ChatGPT advertising from "maybe someday" to "this is actually working." Six weeks after launching its ad pilot in the U.S., OpenAI crossed $100 million in annualized revenue.

OpenAI's nascent ads business surpassed $100 million in annual recurring revenue less than two months after launching its pilot. The company is working with more than 600 advertisers and has seen no impact on privacy-related trust metrics. The company is also beginning to explore additional testing in Canada, Australia, and New Zealand.

The scale of untapped inventory is part of what makes this number interesting. Roughly 85% of ChatGPT users are currently eligible to see advertisements, yet fewer than 20% encounter them on any given day. The $100 million milestone was reached while the system was deliberately throttled, designed to move slowly to protect user experience before scaling.

The advertiser mix is also notable. OpenAI has expanded to over 600 advertisers, with nearly 80% of small and medium-sized businesses signaling interest in ChatGPT ads. The ChatGPT maker is set to launch self-serve advertiser capabilities in April to broaden access and drive further growth. David Dugan, a former top advertising executive at Meta, was named to lead OpenAI's global advertising solutions team.

The self-serve launch in April is the pivotal moment. Right now, getting into ChatGPT ads requires a $200,000 minimum commitment and a direct relationship with OpenAI. When self-serve opens, the barrier drops to whatever a small advertiser can afford to test. That is when you will see the platform's real performance data emerge, because you will have thousands of advertisers running campaigns across different verticals and budgets rather than 600 hand-selected large brands.

For the record, the concern that ads would hurt user trust has not materialized in the data yet. OpenAI reported low dismissal rates for ads and said it has seen no negative impact on consumer trust metrics so far, while citing ongoing improvements in ad relevance as it collects feedback from users and brands. Whether that holds as the system scales and ad density increases is still the open question.

Klaviyo shipped something genuinely important this week that has not gotten the attention it deserves outside e-commerce circles. It matters for any marketer thinking about where email and SMS automation is headed.

Klaviyo introduced Composer, a new agentic experience that generates, optimizes, and recommends full marketing campaigns and flows from a single prompt. A marketer could prompt Composer with "build me a fun spring re-activation campaign, targeting lapsed customers across email and text" and in minutes have a campaign ready to refine and launch. The same conversational interface works for existing flows: ask Composer where a sequence is losing customers, and it tells you exactly what to fix.

The key technical detail that makes this different from a simple AI content tool is what it is drawing on. Every campaign Composer generates is grounded on real customer data and shaped by more than 14 years of marketing intelligence and billions of consumer interactions across Klaviyo's 193,000 customers. Outputs are not based on generic best practices, but on what has proven to work across that customer base. Nothing goes live without human approval.

The co-founder's framing of this is direct and worth sitting with. Klaviyo co-founder and co-CEO Andrew Bialecki said: "The execution layer in software is moving from humans to agents. What matters now is having both the agents that do the work, and the infrastructure that gives them the full picture of the customer."

Composer is currently in private beta, but the broader product release included more than 75 new features. The company also expanded its Customer Agent service with new retail capabilities including order tracking, returns and exchanges, subscription editing, and loyalty lookup, all powered by Klaviyo's unified data platform, giving the agent real-time access to customer profiles and interaction histories.

The strategic implication here is the same one playing out across Meta's Ads Manager, Google's Performance Max, and now Klaviyo: the execution layer of marketing is being automated. The competitive advantage for marketing teams is moving from execution speed toward strategic clarity. The teams that benefit most will be the ones who are very clear about what they want the campaign to accomplish, because the agent can only optimize for goals you actually define. Vague objectives produce mediocre outputs regardless of how powerful the underlying tool is.

OpenAI self-serve advertising opens next month. Here is what to have ready before it does.

The most important preparation is understanding what kind of intent your category generates inside ChatGPT. Spend 30 minutes this week prompting ChatGPT as if you were a potential customer in your category. Search for the problems your product solves, the questions people ask before buying, and the comparisons they make between you and competitors. Note what kinds of responses you get, how detailed they are, and whether your brand or competitors appear organically.

That research tells you two things. First, whether ChatGPT is already functioning as a discovery channel for your category. Second, what the adjacent conversation looks like when your ad would theoretically appear. ChatGPT ad placements appear at the bottom of responses to relevant queries, so knowing what those responses look like informs what copy will feel natural rather than disruptive.

Keep your initial test budget modest. The self-serve platform will be new, reporting will be limited, and the optimization tools will be early stage. A budget sized for learning rather than performance is the right posture for the first two to three months. Set a specific question you want to answer with the test, whether that is CTR benchmarks in your category, cost per click relative to Google, or whether the quality of traffic differs, and measure against that question rather than against your existing channel benchmarks. The context is different enough that direct comparison will mislead you.

2026 is the year AI moves from "cool demos" to real and measurable business use cases. Expect more agentic tools, voice-powered targeting, and a focus on privacy-first data.

Stay ahead of the game by treating your AI reputation like your website. It would behoove you to make your brand easy for agents to understand and cite.

What AI experiment are you running this week? Reply and let me know. I'll feature top stories in future editions! (Everybody loves a good story)

Stay sharp,
Jon
@mistersterling
Chief AI Marketing Geek