Vol 50. Upwork: Tampering with TikTok tropes 🏢

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A trusted tactic in comedy writing is to create surprise. Like when Mitch Hedberg said, “Sorry for the convenience.” Or when Michelle Buteau said, “I don’t look 40 because I’m happy.”

When you create an expectation and shatter it, disrupt patterns, audiences are intrigued. People laugh and pay more attention when they’re surprised. But this isn’t just a tool for comedians.  Upwork used the same tactic to expand their TikTok presence.

This week, Case Studied explores how Upwork increased follower growth and engagement by going against the TikTok trends.

The Brief:

Upwork is a global freelance marketplace, which means their advertising efforts have to reach and resonate with folks who need to hire freelancers and freelancers themselves.

To do that, they leaned into messaging about ditching the “old ways of working.” Think: strict 9-5 hours, in-office mandates, forced commutes, things like that.

Their goal was to “create an ownable TikTok presence that would make Upwork stand out against other B2B competitors like Fiver, Indeed, and LinkedIn.” To do that, they decided to zig when everyone else was zagging.

The Execution:

Upwork partnered with Swift Agency to execute this nuanced idea. Their research revealed that “new ways of working” was a popular conversation topic on TikTok—but all of it, for the most part, looked the same. The subgenre of #WorkTok had a pretty standard formula—it’s a person filming from their desk offering “work hacks” and using green screens to show common enterprise software and title overlays to tell the story.

Together, Upwork and Swift created videos that put a twist on that formula. Just when it looks like a typical #WorkTok video, they would reveal hidden, unconventional twists.

Just look at this video showing someone saying goodbye at the end of a meeting. Once they close their laptop, a new reality is revealed—the room around them is a set that gets taken away, the desk is actually a piece of cardboard on top of an Amazon box, and even the familiar-sounding audio music being played turns out to be a flutist walking through the woods.

Watch now on TikTok

@upwork

BRB 👋🏻 #Upwork #CareerTok #WFH #WorkLife

Upwork and Swift created a string of videos that follow this formula—they play off typical #WorkTok tropes in surprising, fun ways. One video features an office backdrop printed onto a beach towel. Another plays off a key part of TikTok—music—by featuring a custom song about emo CEOs. This one was gets extra points because in general, you don’t see #WorkTok leveraging music very often.

While each video has an element of surprise, the messaging isn’t lost. They cover topics ranging from “how to use AI”  to calendar view “hacks” and Upwork’s actual product.

The Results:

All in all, 20% of Upwork’s new follower growth on TikTok came from this campaign. And compared to the brand’s previous content benchmarks, these videos racked up 417% more views, 218% more engagement, and 225% more impressions.

The Takeaways:

Upwork and Swift did a lot of things right with this campaign. Here are a few that stand out:

1. Leverage Surprise to Break Through the Noise:

Upwork's success on TikTok came from utilizing an unexpected twist to disrupt the norm. In their videos, what starts as a typical #WorkTok clip quickly reveals surprising elements—like a meeting scene turning into a deconstructed set. This disruption catches viewers off guard, ensuring they stay engaged and intrigued.

Brands looking to stand out should consider this approach: break the expectations of familiar content formats to capture attention. The key is balancing surprise with relevance, ensuring that the twist doesn't detract from the core message but instead amplifies it in a memorable way.

2. Reimagine Platform Trends:

Instead of directly copying popular formats like #WorkTok, Upwork and Swift Agency put a creative twist on it. They maintained familiarity by starting with common elements like green screens or desk setups, but quickly flipped the narrative with creative flourishes—whether it’s a flutist walking through the woods or an office setting printed on a beach towel.

For brands, this shows the importance of leaning into trends while reinterpreting them with fresh, unexpected elements. It’s not just about following the trend but also finding ways to innovate within it, keeping content fresh while still relatable to the platform's existing conversations.

3. Deliver Substance with Playfulness:

Even with these surprising and playful twists, Upwork’s videos never lost focus on delivering valuable messaging about relevant work topics, from using AI to scheduling hacks. This illustrates a critical balance for brands—entertainment should never come at the cost of messaging, something that often gets lost in the flashiness of modern advertising

Brands should ensure their content has substance, offering value to the audience while maintaining an engaging and fun tone. This combination of informative content presented through engaging, unexpected formats can help build long-term brand affinity and trust, especially on platforms where entertainment often drives user behavior.

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