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**New Year’s Day 2026:

Show Me the Money (and Please Retire the 2005 Playbook)**

An Open Letter from the OOH Sales Floor

By Brent Baer, Publisher, OOH Today and OOH Owner, baerboards, llc

It’s January 1, 2026… ok, ok, it’s January 5th, 2026. It’s the first day back of the new year for most of you.

The calendar flipped. The champagne is flat. The resolutions are fresh. And across out-of-home, leadership teams are dusting off strategy decks that — if we’re being honest — look suspiciously like last year’s… and the year before that… and the year before that.

Meanwhile, out on the sales floor, we’re already back on calls.

Clients didn’t take the day off from asking harder questions.
Budgets didn’t reset out of nostalgia.
And “that’s not what we do” didn’t magically start closing deals overnight.

So let’s make this a New Year’s post that actually matters.

From the perspective of a seller who respects the past — but lives in the present — here’s the conversation OOH needs to have in 2026.

A Respectful Acknowledgment Before the Roast

Let’s get this out of the way:

Yes, many of you sold OOH 20 years ago.
Yes, you built great businesses.
Yes, you survived cycles, recessions, and more vinyl than anyone should ever have to measure.

But clients aren’t buying your history.
They’re buying solutions for right now.

And right now, the gap between what sales hears and what leadership allows is costing us money.

Or, as Jerry Maguire would say:

“Show me the money.”

10 Questions OOH Leaders Should Be Asking Their Sales Teams in 2026

1. What are clients asking for that we still don’t offer?

If the answer starts with “we don’t do that,” congratulations — you’ve found your first lost deal of the year.

2. What would make a client say YES faster?

Hint: It’s not a longer deck. It’s speed, clarity, flexibility, and fewer internal approvals.

3. Where are we losing deals — really?

Not the polite version. The version sales hears when the client stops sugarcoating it.

4. If you could launch one new DOOH product tomorrow, what would it be?

Sales already knows. Clients already asked. The only question is whether leadership is listening.

5. Which categories are heating up faster than we’re adapting?

Retail, QSR, healthcare, tech, entertainment — the market moves faster than annual planning cycles.

6. Which internal bottleneck costs us the most revenue?

Pricing delays. Legal loops. Approval purgatory. Revenue doesn’t die dramatically — it bleeds out quietly.

7. What are competitors doing better that we pretend doesn’t matter?

The ones you dismissed five years ago? Yeah. Clients didn’t.

8. What could leadership do this month that would unlock more sales?

Not a task force. Not a summit. Something practical. Something usable before Q2.

9. Which policies exist only because “that’s how we’ve always done it”?

Tradition is not a strategy. Nostalgia doesn’t forecast revenue.

10. If you ran this company for 30 days, what would you change first?

This question scares people for a reason — because the answers are usually right.

Revenue doesn’t die dramatically — it bleeds out quietly

The New Year’s Truth

Salespeople aren’t asking to run the company.
We’re asking to help it grow.

We see the friction.
We hear the objections.
We watch money walk away because the system couldn’t move fast enough.

And when leadership listens — really listens — revenue follows.

That’s not rebellion.
That’s alignment.

And when leadership listens — really listens — revenue follows.

A Resolution Worth Keeping

If OOH wants 2026 to be a growth year — not just a rollover year — here’s a simple resolution:

Replace “that’s not what we do” with “tell me more.”

Ask better questions.
Act on real feedback.
Let sales inform product, not just pitch it.

Because in 2026, the market isn’t asking for memories.

It’s asking for results.

And from the sales floor, we’re saying it clearly, hopefully, and with love:

Show us you’re listening.
Show us you’re evolving.
And yes — show us the money.