From Three-Martini Lunches to Three Clicks: What OOH Risks—and Gains—as Buying Goes Programmatic

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

From Three-Martini Lunches to Three Clicks: What OOH Risks—and Gains—as Buying Goes Programmatic

Out-of-home has always been a people business.

Long before dashboards, DSPs, and impression multipliers, OOH deals were built on trust—earned face-to-face, reinforced over time, and often cemented far from the office. In 1980s New York, that trust was forged over three-martini lunches at The Palm, Smith & Wollensky, or Blue Water Grill, where media plans were debated as seriously as baseball standings and the bill quietly reflected the value of the relationship.

This wasn’t accidental. OOH, more than any other medium, demanded local knowledge, judgment, and experience—and the people selling it were often the most reliable translators between the street and the spreadsheet.

Relationship Selling as Market Intelligence

In the industry’s “glory days,” relationship selling wasn’t just hospitality—it was how information moved.

Veteran sellers knew their markets intimately because they lived in them. We’ ride the boards with Bud Hyde, Jack Sullivan, or the RJR and Lorillard guys, touring inventory block by block, the reps learned things no research report could tell you:

• Which boards actually delivered after dusk
• How seasonal traffic really flowed, not how it modeled
• Which municipalities enforced  extension regulations strictly—and which did not
• When construction, weather, or events would quietly affect visibility

Conversations weren’t just social. They were strategic. Decisions were informed by lived experience, pattern recognition, and long memories of what worked—and what failed—in prior cycles.

Clients valued that perspective. Trusting a rep meant trusting someone who had seen the market change over decades, not quarters.

The Value of the Human Layer

Relationship-driven selling brought real advantages:

• Context: Reps understood why a board over-performed or under-performed.
• Judgment: Experience filled gaps where data was incomplete or misleading.
• Advocacy: When issues arose, a trusted rep could fix problems before they escalated.
• Continuity: Long-term relationships encouraged long-term planning.

Yes, it also included entertainment—booze, dinners, events, and the occasional extravagant holiday gift—but the core value wasn’t indulgence. It was confidence. Buyers knew who to call when something went wrong, and sellers had reputations to protect.

Enter Programmatic OOH

Programmatic buying changes that equation.

Automation replaces conversation.
Transactions replace negotiation.
Dashboards replace anecdotes.

And importantly, programmatic solves real problems:

• Faster buying and optimization
• Standardized pricing and access
• Greater transparency and accountability
• Easier entry for new and smaller advertisers

For many clients, this is undeniably positive. Buying becomes more efficient, less subjective, and more measurable. Decisions are driven by performance, not persuasion.

What Programmatic Can’t Fully Replicate—Yet

What programmatic still struggles to capture is nuance.

Algorithms don’t know:

• That a specific corner “feels” different after a new tenant opens
• That there may be a new competitive LOS issue
• That local events, habits, or unwritten rules affect attention

Those insights still live with people—often the same reps who spent years learning markets by walking them, not modeling them.

As buying becomes more transactional, the risk isn’t the loss of relationships—it’s the loss of interpretation.

As buying becomes more transactional, the risk isn’t the loss of relationships—it’s the loss of interpretation.

A Generational Shift in How Relationships Work

Complicating matters is a broader cultural change. Younger buyers communicate differently. They text not call.  They expect instant access to information. Long lunches feel like an obligatory hostage situation.

But that doesn’t mean relationships no longer matter. It means they are formed and maintained differently—through reliability, clarity, and problem-solving rather than proximity and time spent together.

The Future: Not Either/Or, But, Both

The most effective OOH organizations won’t choose between relationship selling and programmatic—they’ll integrate them.

• Programmatic handles scale, speed, and standardization
• Experienced reps provide context, strategy, and local insight
• Data validates decisions; people explain them

In this future, the rep isn’t replaced—they’re repositioned. Less entertainer, more advisor. Less gatekeeper, more guide.

I’ll leave you with this—

The three-martini lunch built an industry by aligning trust with expertise.
Programmatic buying is reshaping it by aligning access with efficiency.

OOH’s challenge—and opportunity—is to ensure that as transactions become automated, the hard-earned wisdom of the market doesn’t disappear with them.

Because even in a world of three clicks, someone still needs to know what’s actually happening on the street.