One marketing decision turns into 6 billboards, 4 creative directions, and a Figma with 50 different options - that’s what we wrestled with for our recent campaign.
Why go down this route with billboards?
I wanted maximum bang for our buck, not the "spray and pray" approach other people seem to love. We didn't know what works yet, so going all-in felt reckless.
Plus, I wasn't interested in the "make people angry for attention" playbook that seems popular these days. That's not us - at least not right now.
I contacted a couple of agencies, and most came back with what I'd call "the usual suspects" - every outdoor concept fell into predictable buckets:
- Direct developer pain
- Feature positioning
- Problem-solution format
What actually resonates?
As I looked through our customer conversations (around 250 of them!), I found a few patterns that seemed to do the trick.
I don’t think developers wake up excited about "cost management". It’s often an afterthought. However, management seems to worry about margins.
The creative direction
During our first round, we did too much explanation.
But it was a bit boring, a bit too many buzzwords if you know what I mean.
During the second round, it was too pithy and clever.
"Building a billing UI is like watching paint dry. But less fun" - Better, but requires too much processing time at 65mph.
I tried to get smart, but it was too much.
Third round: What we actually went with
- "Build agents, Get Paid" - Clear journey, obvious outcome
- "Your everything app for AI Agents" - Positioning without jargon
- "It's not the model, it's the margins" - The key insight
Why these three won
- "Build agents, Get Paid" - Every developer's actual goal. No fluff.
- "Your everything app for AI Agents" - Simple positioning that doesn't require a PhD to understand.
- "It's not the model, it's the margins" - The truth bomb that separates successful AI companies from the rest.

The format strategy
- Bigger wallscapes and billboards (high dwell time) = "Your everything app" works here!
- Smaller formats (drive-by glance) = "Build agents, Get Paid" and "It's not the model, it's the margins"
Being smart about this
Smart budgeting means testing first, scaling second.
We're not trying to piss people off for viral moments. We're trying to solve real problems for real developers.
The billboards are live across SF now - try and find them!
We are, of course, tracking which messages drive the most event signups for our upcoming event, as well as overall site visits. Then double down on what actually converts.
Anyone else taken the "measure twice, cut once" approach to out of home advertising?
Let's see if being strategic beats being loud.
p.s. these aren't as expensive as you think they'd be.
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