{"id":129483,"date":"2026-06-03T02:20:23","date_gmt":"2026-06-03T02:20:23","guid":{"rendered":"https:\/\/mailinvest.blog\/index.php\/2026\/06\/03\/openai-needs-two-cmos-because-it-has-a-problem-marketing-cant-solve\/"},"modified":"2026-06-03T02:21:22","modified_gmt":"2026-06-03T02:21:22","slug":"openai-needs-two-cmos-because-it-has-a-problem-marketing-cant-solve","status":"publish","type":"post","link":"https:\/\/mailinvest.blog\/index.php\/2026\/06\/03\/openai-needs-two-cmos-because-it-has-a-problem-marketing-cant-solve\/","title":{"rendered":"OpenAI Needs Two CMOs Because It Has a Problem Marketing Can’t Solve"},"content":{"rendered":"

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Here’s a advertising riddle: Take top-of-the-line B2B model builders alive, give him an enormous title, a near-trillion-dollar firm to market, and probably the most well-known product on earth to promote.\u00a0<\/p>\n

Why would that be a catastrophe ready to occur?\u00a0<\/p>\n

Welcome to Colin Fleming\u2019s new job at OpenAI.<\/p>\n

Fleming is the true deal. 13 years at Salesforce, culminating as evp of worldwide advertising. Two years as CMO of ServiceNow, working wonders. He is aware of how one can take a posh B2B product, construct a model round it, and drive pipeline. He isn\u2019t the form of marketer you rent when you’re severe about enterprise income, he’s actually on the very high of the record. However he could also be strolling into the toughest advertising job on the planet.<\/p>\n

Fleming joins<\/a> as CMO, Enterprise\u2014a brand new title, intentionally scoped to OpenAI\u2019s enterprise push. His predecessor, Kate Rouch, stepped down <\/a>in April after combating late-stage breast cancer<\/a> by means of her whole tenure. She led international campaigns, ran back-to-back Tremendous Bowl advertisements, constructed the advertising operate from the bottom up, and did all of it whereas present process therapy. A rare act {of professional} dedication.\u00a0<\/p>\n

However OpenAI\u2019s model is in bother proper now. Begin with the structural chaos. Within the house of some weeks earlier this yr, the corporate misplaced its CMO, its COO transitioned to a obscure \u201cparticular tasks\u201d position, its head of product took medical depart, and a sequence of senior researchers walked out. The corporate is concurrently making ready for an IPO whereas projecting losses of $14 billion by the top of 2026.\u00a0<\/p>\n

That isn’t a secure platform from which to construct an enterprise model.<\/p>\n

Then there’s the promoting determination. In January, OpenAI confirmed it will start running ads<\/a> inside ChatGPT\u2019s free tier. The format is contextual, clearly labeled, separated from responses. Rationally all of it is smart. Enterprise and paid tiers stay ad-free. OpenAI insists the advertisements won’t affect ChatGPT\u2019s solutions.\u00a0<\/p>\n

However we don’t stay in a rational world, even within the extremely processed realm of AI. A Harris Ballot survey taken within the days earlier than launch discovered that 75% of Individuals would belief AI buying suggestions much less if its outcomes have been sponsored. Whenever you await solutions from a blinking cursor, solutions you don\u2019t know the reply to, belief turns into the one most essential asset OpenAI has, particularly within the enterprise market.\u00a0<\/p>\n

Fleming understands this territory higher than nearly anybody. His whole profession has been constructed on the precise problem of promoting to procurement committees, convincing CFOs, and constructing the form of sustained model credibility that closes enterprise offers.\u00a0<\/p>\n

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Salesforce beneath Marc Benioff was the grasp class in B2B brand-building: clear positioning, large share of voice, distinctive model belongings, relentless buyer success storytelling. Fleming absorbed all of it, a lot in order that ServiceNow adopted the identical playbook, and may even have utilized it higher. He is aware of precisely what enterprise patrons want to listen to, and the way usually they should hear it.<\/p>\n

However Fleming\u2019s Salesforce instincts will now collide instantly with the OpenAI actuality.\u00a0<\/p>\n

Salesforce and ServiceNow offered belief as their core proposition. Their clients willingly handed on delicate information, crucial workflows, income operations. The model promise was: we’ll by no means screw you.\u00a0<\/p>\n

That promise was credible as a result of neither firm confronted a structural battle between its client product and its enterprise product. OpenAI does. The free ChatGPT that runs advertisements is similar mannequin enterprise clients are being requested to belief with their most delicate inner information. That dissonance isn’t trivial.<\/p>\n

Then there’s the aggressive context. Anthropic is all of the sudden the beast within the room. It’s rising sooner, smarter, cleaner, and it\u2019s successful within the regulated industries\u2014monetary companies, healthcare, authorized\u2014the place enterprise offers are greatest and belief issues most.\u00a0<\/p>\n

In the meantime Google\u2019s Gemini is slashing costs and going after developer mindshare. Fleming isn’t coming into a market the place OpenAI can coast on model halo. He’s coming into a knife struggle with a smaller-than-expected pocket knife, and going through a man with the machete and a girl with a limiteless arsenal of throwing daggers.<\/p>\n

The twin-CMO construction can also be a possible concern. OpenAI has cut up advertising into two roles: one for client, one for enterprise. Offered as sophistication, it\u2019s truly an admission of battle. The patron model and the enterprise model have diverged to the purpose the place one particular person can’t credibly handle each. That could be a technique downside, and never one Fleming can simply clear up.<\/p>\n

None of this ought to be learn as a prediction that Fleming will fail. He’s precisely what OpenAI wants. If anybody can construct a reputable B2B model on high of a messy underlying actuality, it’s somebody along with his monitor report.\u00a0<\/p>\n

However good hires don’t all the time repair declining fortunes. They work inside them, round them, and typically regardless of them.\u00a0<\/p>\n

The true query for OpenAI isn’t whether or not Fleming is gifted sufficient for this job. The query is whether or not the corporate is prepared to make the more durable strategic selections that Fleming will inevitably ask. About product separation, in regards to the promoting mannequin, about what OpenAI for Enterprise truly stands for.\u00a0<\/p>\n

Hiring a marketer like Fleming is simply the beginning of the issue being sorted.\u00a0\u00a0<\/p>\n<\/div>\n