Everyone claims they want a unicorn Digital executive. A rare beast. A corporate spirit guide who will drag the enterprise into the future by sheer force of will. But nobody talks about what happens after the photo‑op and the press release. The truth is uglier. The unicorn ends up in a boutique hotel inspired conference room in Parsippany or Deerfield where ambition goes to die under soft pendent lighting and the faint smell of ethically sourced eucalyptus. It sits across from a sleek slide deck and a VP of Strategy who has never once carried a revenue number but speaks with the serene confidence of someone who has never been proven wrong. The dream doesn’t fail in the market. It bleeds out quietly in the calendar invite.
I’ve spent twenty years shifting between IT and the Business, and I can tell you the hallway between them is the most desolate stretch of real estate in American enterprise. A no‑man’s‑land of jargon, suspicion, and performative alignment. They communicate like strangers trapped at a bad dinner party: talking constantly, listening rarely, and learning nothing. IT speaks in architecture. The Business speaks in adrenaline. Neither has the patience to translate. The siloed org chart reflects this, and, in many cases, it was designed to make sure nothing ever has to change.
You can see the trap right there in the job description. Strategic and hands‑on. Visionary and operational. Business‑minded and technically fluent. It reads like a ransom note assembled from the corpses of every failed big 3 consultancy transformation that came before it. The unicorn immediately hits walls. Walls that no one mentioned during the interviews because no one inside can see them anymore. Long exposure to structural dysfunction numbs the senses. People stop seeing the structure. They see only the culture, which they describe without irony as collaborative.
Who’s done it well? Unilever, Nestle, Sanofi. Walmart. But they are a lonely group. Most miss the mark with such mystical incompetence it borders on performance art.
If you want the unicorn to actually survive, let alone succeed, you need three things:
- Real cross‑functional authority with fiscal teeth, not a dotted line and a pep talk.
- A seat at the table where strategy is born, not the room where it’s announced like weather.
- A public acknowledgment that technology and business are the same endeavor, and always have been. The org chart simply refused to notice.
Without these conditions, you haven’t hired a bridge builder. You’ve hired a talented human being to stand in the rubble and write theoretical reports about how a bridge might be built if the laws of physics and corporate politics were different.
The companies that get this right build the terrain before they go unicorn hunting.
Everyone else is left clutching press releases, prayers, and a LinkedIn post about being “thrilled to announce” a hire who never had a chance. Start with the design. Start with the structure. Start with the truth. The talent will find you. The unicorn always does. The real question is whether you’ve built a place worthy of one.