BoSacks Speaks Out: Who’s Your Head of Preparedness?

BoSacks Speaks Out: Who’s Your Head of Preparedness?

OpenAI just posted a job that should make every publisher sit up straighter and check their pulse. It is not another “culture-first” HR posting with a stock photo of smiling people high-fiving in a glass conference room. It is a neon warning sign with a serious salary attached.

Sam Altman wants a Head of Preparedness. Not for PR. Not for growth. Not for hype. For survival. Someone paid to imagine the worst before it happens.

Translation: they are hiring a professional doomsday thinker, except the doom comes with spreadsheets, simulations, and uncomfortable slide decks.

Here’s the kicker: that’s exactly what publishing needs.

We used to have this muscle

Decades ago, Time Inc. understood something that too many media companies have forgotten: you cannot “optimize” your way out of a future you refuse to look at.

They had tech visionaries on staff. Some were my friends, people paid to look past next quarter’s ad pages and ask the dangerous question: What’s coming that could break us?

They sniffed out cable’s impact on attention, desktop publishing’s impact on production workflows, early online services, and the first hints of digital distribution long before those words became “strategic initiatives” on a consultant’s invoice.

And yes, there was Bo, loud, persistent, and often annoyingly correct, ranting about databases, PDFs, websites, digital workflows, copyright, and later AI. That wasn’t futurism for sport. That was survival with a better vocabulary.

Now we mostly run yesterday’s playbook, really well

Fast-forward to now: most publishing companies have lost that preparedness muscle. In its place, we have brilliant operators running the show, masters of yesterday’s optimization. They can trim costs, renegotiate print, consolidate vendors, squeeze the budget until it whimpers, and keep the trains running on time.

But ask them who is paid to worry about what might kill the business in five years and you get blank stares, nervous laughter, or the corporate equivalent of a shrug.

That is not short-sighted. That is insane.

And please do not tell me “it’s everyone’s job.” That is what people say when it is nobody’s job.

Publishing is sitting in a blender, and it’s set to purée

Publishing today is dealing with multiple threats that interact, which is the part everyone keeps missing.

• AI upheaval that changes how people find information
• Collapsing search traffic (the polite term is “shifting discovery,” the honest term is “Google stopped sending love letters”)
• Content scraping and training usage that turns your archive into someone else’s product feature
• Platform chokeholds, where distribution is rented, not owned
• Creator economics, where individuals can outmaneuver institutions
• Eroding physical distribution, with retail shrinkage, plant closures, and postal hikes

And we think an Editor-in-Chief, a CRO, and a CFO can handle all of that on top of their day jobs? That’s not leadership. That’s corporate malpractice with a nice logo.

What a Head of Preparedness actually does (no, it’s not gloom)

This role is not doom and gloom. It is strategic radar. Someone living one to five years ahead of the business, tracking weak signals before they become broken revenue lines.

Think of this person as your future-defense editor. Their job is to reduce surprise.

They do four things relentlessly:

1. Threat modeling (the stuff publishers hate because it feels negative)
   Not “what could go wrong?” but “what is likely to go wrong, how soon, and what does it break first?”
2. Scenario planning (war games without the body counts)
   They run tabletop exercises so leadership can see failure modes while there’s still time to steer.
3. Opportunity spotting (yes, it’s also about upside)
   Preparedness is not only defensive. It also flags new product models, licensing plays, and distribution pivots early enough to matter.
4. Executive forcing function
   They show up with uncomfortable data and refuse to let the strategy meeting become a bingo game of buzzwords.

Let’s make this painfully practical. A Head of Preparedness would walk into your leadership meeting and force conversations like these, with specific scenarios and actions.

Who should own this role?

Call it Head of Preparedness, CVO (Chief Visionary Officer), Strategic Radar Lead, I don’t care. Just don’t bury it three levels down where it can be ignored.

This person needs:

• Access to the CEO and board
• Authority to convene cross-functional teams
• A mandate to challenge assumptions without being labeled “negative”
• A dashboard that includes platform changes, AI policy shifts, licensing activity, distribution economics, and audience behavior trends

If you treat the role like a “nice to have,” you will get exactly what you paid for: a nice memo and a slow death.

What this looks like for a small publisher (yes, even a two-person operation)

If you are a two-person Substack or a small niche magazine, you cannot hire a $555K doomsday executive. Fine. You still need the function.

Make it a standing discipline:

• One hour a week: “What changed in the ecosystem?”
• One hour a month: scenario drill (pick one threat, map impact, decide counter-moves)
• One quarter a year: a full preparedness review (revenue dependence, distribution dependence, platform dependence, IP exposure)

Preparedness is a role before it is a title.

The BoSacks Bottom Line

Publishers keep getting blindsided by the same category of problems and then acting shocked. First Facebook. Then Google. Then programmatic. Then Copyright. Now AI. The postmortem always sounds the same: “We didn’t see it coming.”

But that’s never true. Some people saw it coming. They just weren’t at the leadership table, or they were dismissed as alarmists until the building was already on fire.

A Head of Preparedness doesn’t run the company. They protect its future. They bring uncomfortable data, ugly scenarios, and inconvenient truths into the room before the room fills with smoke.

OpenAI is paying someone to imagine how their own technology could go sideways. Publishers are still pretending the world will politely wait for their next budget cycle.

If AI companies need a Head of Preparedness to survive their own success, publishers need one to survive everybody else’s success.

Now the uncomfortable question: who’s yours?