Welcome to all the new readers who joined us this week. The audience has grown rather quickly of late, which is making me nervous. Just don’t stare, okay 😄

As we pulled this edition together, one theme kept surfacing: companies trying to modernize without breaking in the process. DoorDash is building a commerce-media machine on top of delivery infra. Smashburger is trying to turn recovery into routine behavior. OpenAI is splitting marketing leadership because enterprise and consumer AI are different kingdoms.

Different categories, same pressure: growth is no longer enough. Companies now need to handle more complexity than they were originally built for. To do this, they hire new CMOs.

Before we get into this week's appointments, let's look at the to-and-fro.

May was a busy month for departures, but hiring activity eased slightly after a frenetic Spring. Following 49 new CMO appointments in both March and April, May saw 37 announced globally: 23 women and 14 men. 10 were internal promotions, while 27 were external hires. Notably, 20 of the new appointees had never held a CMO title before, reinforcing what we already knew: boards are becoming more comfortable backing first-time marketing chiefs. Industry expertise, however, remains highly valued: only 2 appointments involved executives moving into an entirely new sector. Shelve your pivot plans for now.

The U.S. remained the most active market, with 20 CMO appointments across 10 states. California led the way with 6 hires, followed by Massachusetts and New York with 3 each, and Illinois with 2.

Outside the U.S., momentum picked up. England announced 4 new CMOs, India hired 3, while Canada and Australia each welcomed 2. France, Singapore, Sweden, Cyprus, South Africa, and Germany all recorded one new appointment.

By sector, technology continued to dominate with 15 new CMOs, followed by Media, Sports & Entertainment with 5. Financial Services and Retail each appointed 4, while CPG and Professional Services added 3 apiece.

I sat down with Ad Age this week to discuss OpenAI’s reported move. Splitting marketing leadership across two CMO roles, which says a lot about the position the company now finds itself in.

OpenAI is at a valuation and set of expectations that require it to win in two very different worlds.

The reported appointment of Colin Fleming as their Chief Marketing Officer, Business points directly at enterprise growth becoming its own operational priority. Fleming spent 13 years inside Salesforce before becoming CMO at ServiceNow, building a career around enterprise platforms, product marketing, category expansion, and helping large organizations understand complicated technology well enough to adopt it at scale.

That counts because the next phase for OpenAI looks far trickier than growing ChatGPT usage.

Consumer AI and enterprise AI do share underlying models, but they behave very differently. One side revolves around habit formation, pricing, speed, cultural relevance, and making products useful often enough that people keep returning. The other revolves around much drier stuff - procurement, governance, integration, compliance, security reviews, reliability, and convincing major organizations that OpenAI belongs deep inside core workflows.

Large enterprises are also asking tougher questions now. Some want external partners. Others are exploring internal AI stacks, open-source models, or hybrid approaches where they believe long-term control and governance may be safer. In the C-suite, everyone wants to be seen as earnestly and wisely steering these decisions.

At the same time, Anthropic appears to be gaining serious traction in enterprise and developer circles (anecdotally, CTOs I talk with prefer Claude).

Public business-spend data from Ramp recently showed Anthropic overtaking OpenAI in paid business adoption for the first time, while operator chatter around Claude in coding and regulated-industry environments grows louder.

That puts OpenAI in a difficult position.

The company has to preserve the speed and cultural momentum that made ChatGPT explode globally while simultaneously becoming credible enough for boards. And I can only imagine the consensus required to align CHROs, CDOs, CPOs, CIOs, CFOs, CISOs, and procurement teams at this consequential time.

In one world, the consumer side, we expect wild experimentation (eg Sora), velocity, rapid iteration, and constant engagement growth. Meanwhile, enterprise buyers generally reward stability, predictability, governance, and risk reduction. Even the internal language around success starts to change once those motions mature.

That is why the dual-CMO structure is interesting. On paper, investing in specialization makes sense. In practice, building two powerful marketing organizations around very different mandates can create strain: competing priorities, duplicated influence, conflicting narratives, and internal fights over what the OpenAI brand means.

Fleming’s own public comments after joining OpenAI leaned heavily toward operational acceleration: ideas becoming prototypes faster, companies learning faster, customers experiencing value faster. The language is comforting and syrupy for B2B buyers.

Even his LinkedIn summary explains the assignment in that tone:
“translating complex platforms into clear, differentiated narratives that drive adoption, ecosystem growth, and category leadership.”

The world is already paying attention to AI. That’s not the job. Fleming needs to get people to trust it.

DoorDash is putting a media-first operator, and a first-time CMO, in the seat. That tells you where the company thinks the work is now: getting more people to use it more often, in more categories, and in more places. And selling ads.

The ads business is already material. DoorDash has said DoorDash and Wolt Ads crossed more than $1 billion in annualized revenue run rate in 2024, with more than 150,000 advertisers across 30+ countries. This is one of the clearest paths to making a delivery platform look more like a local commerce business.

The core marketplace is growing fast enough to fund that ambition. In Q1 2026, DoorDash reported Marketplace GOV growth of 37% year over year, revenue growth of 33%, and adjusted EBITDA of $754 million. The question now, is whether it can keep widening the business without making the whole thing feel too expensive, too crowded, or too dependent on restaurant delivery.

The ads team has momentum. Toby Espinosa, DoorDash’s VP of Ads, has been framing the opportunity around real buying behavior and measurable growth, with interest targeting, retailer-level sponsored products, and category-share insights built around actual purchase intent. DoorDash also expanded the product in June 2025 with AI-powered tools and the acquisition of Symbiosys, which it said would add offsite advertising and closed-loop measurement.

That is a clear sign that DoorDash wants ads to do more than monetize app traffic. It wants them to become a serious commerce-media engine.

Tim is walking into big shoes. Outgoing CMO Kofi Amoo-Gottfried joined DoorDash in 2019, when it was still a private company last valued at roughly $16 billion. He leaves with DoorDash public, global, and worth about $72 billion. That growth was not all marketing, of course; DoorDash is an operations, logistics, product, and density machine. But Kofi helped make the brand feel bigger, broader, and much more culturally fluent as the company moved beyond restaurant-delivery utility. His best work helped explain the business. “All the Ads” was the clearest example.

So yes, the strategic read on this hire is straightforward. Castree’s background in media, global marketing, and large-scale performance systems fits a company that now has to manage growth, category expansion, membership, and ad monetization… at the same time.

I’ve worked with Tim directly. He’s curious, skeptical, and willing to take some risk. His roots run back to Leo Burnett, but his operating center of gravity is media math. That matters here.

This marketing job is about making the platform feel useful often enough that the ads business, the membership business, and the delivery business all reinforce each other.

Tim can do that.

The U.S. restaurant industry has been unusually active at the top of marketing in 2026. Popeyes, White Castle, P.F. Chang’s, Chick-fil-A, Jimmy John’s, City Barbeque and Chipotle have all changed CMOs this year as chains wrestle with slowing traffic, shifting value expectations, digital ordering habits, loyalty economics and fragmented consumer attention. Everyone appears “hungry for growth” (ed: sorry), but the more interesting question is what kind of marketer restaurant brands now believe can quell the appetite for change.

Smashburger has hired Kate Savelli as Chief Marketing Officer during this moment.

This is a business trying to move from stabilization back into expansion. After years of declining unit count and a shrinking footprint, Smashburger says it plans to open 10 to 12 new restaurants in 2026 while continuing a broader brand rebuild already underway.

Savelli arrives from Bagel Brands, where she worked across Einstein Bros. Bagels on brand and performance marketing, digital guest experience, media strategy and loyalty systems. Earlier roles at Cheddar’s Scratch Kitchen and Darden Restaurants gave her exposure to scaling restaurant operations, but her public commentary reads more modern‑retail- and consumer-systems-oriented than classic restaurant advertising.

Her LinkedIn posts keep returning to frequency, occasion‑building, media efficiency, AI‑era discovery and value beyond discounting. One line stands out: “Simply cutting prices, simply won't cut it in 2026.” That feels highly relevant to Smashburger, whose recent recovery appears heavily tied to value offers, menu innovation and traffic recovery. Trade reporting indicates same‑store sales swung back into positive double‑digit territory by early 2026 after earlier declines.

Savelli has also been unusually blunt about pressure inside fast casual. She’s questioned whether parts of the category have “optimized itself out of an occasion” as pricing drifted toward casual dining while QSR players improved food quality and convenience. It’s a sharp observation: consumers buy routines, convenience, little rituals and places that become part of the week, not just single transactions.

Her first reflections after joining Smashburger were tactile and operational - fresh‑cut toppings, Chicken Smash obsession, Häagen‑Dazs shakes, guests visiting every single day, “founder vibes.” The emphasis landed on product conviction and guest behavior rather than polished corporate positioning.

At the same time, she displays fluency in modern marketing systems. Her posts reference attribution gaps, AI‑powered search behavior, owned‑channel optimization, performance media, and loyalty economics with a level of comfort that is still relatively uncommon in restaurant leadership. She’s also willing to publicly question category assumptions - dissecting big tent‑pole spending when precision, targeting and discovery may now do more for ROI than spectacle.

Smashburger’s challenge is straightforward: stronger awareness, more repeat behavior, healthier unit economics and renewed franchise confidence, all while competing in one of the noisiest categories in American consumer business. Savelli understands that frequency and belief travel further than noise.

The test for Savelli is simple: can she convert short‑term traffic and promotional gains into daily routines, healthier unit economics and franchise momentum? If she succeeds, Smashburger moves from recovery to durable growth. If she fails, the chain risks slipping back onto the discount treadmill.

Three brands, three CMOs, one question: can you modernize without breaking what worked? DoorDash is betting yes. Smashburger is praying yes. OpenAI is hiring two people to figure it out.

Here's what I know that you don't: since January, over 210 CMOs have moved. Some got promoted. Some got pushed. A few just got bored.

Every single one of them is now sitting in a spreadsheet on my desk: names, old roles, new roles, industries. The whole messy map of who is going where in the world's most expensive game of musical chairs.

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