Feature BY Erin Behrens | February 18, 2026

When Chatbots Start Showing Ads, Who Wins?

Super Bowl viewers accustomed to the usual peppy ads for snacks and car insurance were treated to a new wave of brands competing for attention during last week’s game: dueling AI platforms. Ads for OpenAI took an earnest tone, promoting the use of its Codex tool for creators with the theme, “You Can Just Build Things.” But its archrival Anthropic, on the other hand, went on the attack, aiming to gain an advantage over a question on every marketer’s mind: when will advertisements start appearing in the answers to our AI prompts? Anthropic’s ads formed a quick response to the announcement of paid ads coming to OpenAI’s ChatGPT. The opening round in the Super Bowl foreshadows an exciting time for marketers, a confusing time for consumers, and a hypercompetitive time for these leaders in AI. Anthropic’s Super Bowl campaign, touting its Claude platform, offered a calculatedly dystopian glimpse of ads in AI. In the commercial that drew the most attention, the lead asks, “Can I get a six-pack quickly?” His extra-jacked training partner recommends, in a suspiciously lagging monotone, that the kid try “Step Boost Maxx, the insoles that add one vertical inch of height,” leaving the youth confused as the slogan flashes: “Ads are coming to AI. But not to Claude.” Anthropic says it will support Claude through paid subscriptions, among other means.The commercial lead asking his training partner for advice (photo via Anthropic) Meanwhile, OpenAI is positioning this change as pragmatic. The company’s CEO, Sam Altman, has framed ads as a way to make the service more accessible. Sponsored placements may be tested for users on the free plan, with clear labeling and a separation from core answers, the company posted. The stated goal is to fund the platform while preserving trust, ensuring users can distinguish between helpful guidance and promotional content. Rethinking Marketing Strategies The looming reality of sponsorships on AI platforms is sure to alter marketing strategies. “Sponsorship on AI platforms is right around the corner, especially as these tools mature and look for sustainable revenue models,” Katie Conrad, general manager of customer performance and insights at Delta Air Lines, told From Day One.“We’re already seeing high-intent behavior shift into AI, from Cyber Monday shopping to full trip planning, which means brands are entering the consideration set earlier than ever,” Conrad said. Instead of scrolling through search results, a consumer might ask a chatbot, “What’s the best 65-inch TV?” or “Which standing desk is worth it?” These high-intent questions could easily and quickly be solved as sponsored content makes its way to chatbots. If AI becomes the first stop for answers, it also becomes a battleground for brand visibility. Companies will increasingly optimize not just for clicks, but for being the answer, positioning themselves within AI-generated recommendations in ways that feel authentic and helpful to consumers.Preserving Brand and IntegrityThese ads will likely be hyper-targeted, a dynamic that will land in a variety of ways with consumers. Some will appreciate ads that feel genuinely helpful, while others may see that level of precision as invasive. “People will value authentic content that showcases your lived experiences and POV instead of informational content,” said Sooraj Divakaran, marketing director at Firstsource. Even so, “[marketers] will need to be very thoughtful with how they use this new channel and what they want to achieve from it. The larger question is how the sponsorship will align with what you’re trying to do as a brand,” Divakaran said, citing the case of Anthropic’s recent partnership with the Williams F1 auto-racing team as their official thinking partner. “If what you’re trying to do as a brand is closely aligned with any of these brands, then the partnership will make more sense,” Divakaran said.When it comes to brand trust, the stakes are high. AI carries a sense of authority while also feeling personal, almost like a one-to-one conversation. That combination is powerful yet fragile. Sponsored suggestions that feel pushy or misleading could backfire quickly, much like in the satirical Super Bowl scenario Anthropic depicted. “The challenge will be protecting trust, because the power of something like ChatGPT is perceived objectivity, so any sponsored presence has to feel native, transparent, and genuinely useful or it risks eroding the very behavior brands want to tap into,” Conrad of Delta said. The Chatbot Super Bowl FeudWhile OpenAI CEO Sam Altman emphasizes accessibility, Anthropic’s ads clearly made an impact, according to post-game data. “The maker of the Claude chatbot saw visits to its site jump 6.5% following its Super Bowl advertisement that took a swing at rival OpenAI’s decision to bring ads to ChatGPT,” reports CNBC. The ad put Claude into the top 10 free apps on the Apple App Store and drove an 11% increase in daily active users, outperforming competitors like OpenAI, Google Gemini, and Meta.Was it just an effective ad, or is it tapping into deeper consumer insights? The Super Bowl spot for Claude may have driven clicks and installs, but it also raises a bigger question: how comfortable are users with advertising in this new form of media that takes on the role of a trusted advisor? Customers are used to seeing pay-per-click (PPC) ads appear in search-engine results, usually posted above the list of non-paid results, but AI chatbots started off with non-commercial personas. As they become the first stop for information, from shopping recommendations to trip-planning, users may start noticing sponsored responses in places they previously expected neutrality. Brands see opportunity, but the presence of ads in AI could shift trust, influence behavior, and even change how people interact with these platforms. The competition has only begun, but Anthropic’s campaign may be signaling the new rules of engagement.Erin Behrens is an associate editor at From Day One.(Featured photo by alexsl/iStock)

Story cover image
Live Conference Recap BY Grace Turney | February 25, 2026

Employer Listening With Intent: From Feedback to Follow Through

Around 2009, a few years into his career at CarMax, Craig Cronheim had a habit he now describes with a mix of nostalgia and self-awareness. After visiting a store, he’d board a plane home to Richmond with a mental list of every question and suggestion he’d heard from associates that day, and he’d stay up working to resolve each one. “I thought I was the feedback loop,” he said. It worked, for a while. But as his responsibilities grew, Cronheim learned something that has shaped CarMax’s entire approach to employee listening: personal accountability can only scale so far. The infrastructure has to carry the weight.Cronheim, SVP and chief HR officer at CarMax, shared that progression during a fireside chat during From Day One’s Washington, D.C. conference. Moderated by journalist Krissah Thompson, the conversation explored how CarMax has built a disciplined, trust-generating feedback system across a workforce of more than 28,000 associates.Cronheim was careful to make an important distinction: “Listening is the beginning, but not the end,” he said. At CarMax, the process follows three steps: understand, act, and close the loop. Each stage matters, but the third is where trust is either built or broken.“You can collect the feedback. You can actually do something with it. But if your teams don’t know what you’re doing with it, and they don’t know why, you’re really missing out,” Cronheim said. “They’re not going to trust you, because they’re going to see some action, but they’re not going to be able to connect the dots.”A Well-Oiled Feedback MachineTwice a year, CarMax surveys every associate, says Cronheim. The response rate hovers around 90% – a figure Thompson found remarkable for an organization its size. Cronheim credits the consistency of follow-through, rather than traditional incentives. “What we incentivize with is taking action on the feedback,” he said. After each survey cycle, two tracks run in parallel. Managers at all CarMax locations receive their team’s results and are required to submit an action plan. An astounding 87% did so in the most recent cycle, he says. Meanwhile, centralized HR home office teams receive aggregated feedback sorted by topic and develop their enterprise-wide action plan. The whole picture is then packaged into an all-associate communication CarMax calls “Your Feedback in Action,” which outlines major themes of associate feedback, and what the company is doing to respond to it. CarMax has also begun using AI to analyze open-ended survey comments, helping teams identify sentiment patterns across thousands of responses. Cronheim noted the company is deliberate about boundaries: “We’re using AI on feedback that’s already been offered. We’re not using broader AI sensing tools to understand what our teams are doing or saying unless they’re giving us that feedback directly.”Maintaining the Routine in Rough PatchesThompson, who referenced her own experience navigating difficult workforce decisions during her time at the Washington Post, asked how CarMax keeps its feedback commitments when times get hard. Cronheim didn’t sidestep the question. “We’re in a tough stretch right now,” he said, noting the company is between CEOs and has had a couple of difficult sales quarters. “We have a survey going out on March 16, and we will run the same exact play that we do when times are good.” Craig Cronheim, CHRO at CarMax, spoke about "Employer Listening With Intent: From Feedback to Follow Through" at the D.C. conferenceThat consistency, he says, is precisely what protects trust. When the company can’t deliver on what associates ask for, it says so, and explains why. “At least acknowledging that, and saying, ‘You told us this, we can’t do that right now, here’s why, but here’s what we will do’ – that helps build trust even when you’re not able to deliver on the immediate request.”Feedback That Changed the CompanyOne of the clearest examples of the system working came from the shop floor. Store associates had long complained about the time-consuming daily process of scanning inventory—sometimes as many as 400 to 500 cars, and often in extreme weather conditions. CarMax heard the feedback, spent several years researching solutions, and ultimately implemented a GPS-based system that handles real-time inventory tracking automatically. “It’s been one of the most popular things we’ve done in my nearly 19 years at the company,” Cronheim said.The approach to storytelling around that change mattered just as much as the technology itself. Cronheim now uses specific associate suggestions as teaching moments, naming the person and idea when sharing updates with broader groups. “I’m signaling to a much larger audience: we want feedback, we listen to feedback, and we take action,” he said. “That gives a broader group a sense of how important it is, and how it’s the expectation of every last leader.”Other feedback-driven changes at CarMax include the introduction of parental leave, revisions to time-and-attendance policies, and updated uniform guidelines. The expectations employees bring to surveys have shifted too. “It used to be primarily about pay or schedule,” Cronheim said. Increasingly, associates want to know how the organization will support them through personal and community struggles, which has been the impetus for CarMax to expand its benefits and equip managers for a more complex role.For leaders looking to start somewhere, Cronheim’s advice was simple: audit your own listening. “If you’re not actively asking your team, your customers, and your fellow leaders how you and your function can be doing more and better, you’re missing an opportunity.”Grace Turney is a St. Louis-based writer, artist, and former librarian. See more of her work at graceturney17.wixsite.com/mysite.(Photos by Josh Larson for From Day One)

Story cover image