Beyond the Uncanny Valley

Introducing AI to a Live-Action Giant

ClickUp isn’t just a software company; they are a content powerhouse. With an in-house team of full-time actors and videographers, they’ve built a massive following on “human-driven” corporate humor. When they approached me to explore AI video, the stakes were high: we had to go viral without hitting the “Uncanny Valley” or diluting the high-quality brand identity they had spent years building.

The brief was simple: Make it viral, make it funny, and make AI work for a brand that lives on human connection.

The "Strategic Restraint" of Universal Truths

To protect the brand, I had to be honest about the technology’s limits. Instead of forcing AI to do “human talking heads”—which can often feel “uncanny” and robotic, I pivoted the focus to a universal human constant: The To-Do List.

We decided to look back at 1.5 million years of human productivity. We could use AI to achieve a massive historical scale that would be impossible (and budget-prohibitive) for a traditional film crew.

The "Retention Hack" and Sound-Off Strategy

In an environment where users are ruthless with their time, I chose a historical listicle .

  • The Retention Hack: Lists are a powerful psychological trigger. By moving through time, we created a natural “What’s next?” curiosity that kept viewers watching until the very last frame.
  • Visual Payoffs: We didn’t wait for a single punchline at the end. Instead, we peppered the timeline with “mini-payoffs” absurd, historically-themed to-do lists.
  • Sound-Off Optimization: By using bold, stylized text-on-screen as the primary driver of the story, we ensured the ad was just as effective in a silent LinkedIn feed as it was with the sound on.

From "One Experiment" to "One a Day"

The response was immediate and record-breaking for the ClickUp team.

  • Great engagement: The video became one of ClickUp’s most-engaged pieces of content on LinkedIn, with shares from external accounts carrying the brand far beyond its existing audience.
  • New Customer Intent: Beyond the “likes,” the comments had people stating they wanted to check out ClickUp.
  • The VP’s Call: The day after launch, ClickUp’s VP of Marketing requested a roadmap for AI content production.

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