Playing it safe is supposed to be the sensible choice. Luke Winter, the founder of comedy video studio Deadpan Agency, would disagree. 

Luke spent fifteen years running a corporate video agency, making the kind of polished B2B video content that's meant to build trust and generate leads. It worked, until he got bored. So, he sold his side to his business partner, took some time out in Bali, and founded Deadpan - a comedy video studio helping brands willing to be funny in categories that mostly aren't. 

Deadpan and Content 10x share a client. Vector's VP of Marketing, Jess Cook works with both agencies, and she's no stranger to the podcast either. It's easy to see why she rates Deadpan: one of their comedy campaigns drove a 33% jump in Vector's branded search, a 22% increase in demo requests, and a 44% increase in pipeline. 

Amy and Luke get into where B2B marketing humor comes from in a client brief (it starts in a far more boring place than you'd expect), how Luke gets a nervous CEO or CFO comfortable enough to greenlight the riskier idea over the safe one, and why his preferred first step for a brand testing comedy is surprisingly simple: make a meme. 

Try naming a B2B ad you've seen in the last month. Not a company you remember. Not a product you use. An actual ad. 

It's surprisingly hard, isn't it? 

That's where Luke starts. Look at LinkedIn, company websites, YouTube channels, and, well, most of it starts to blur together. There is no shortage of B2B content. If anything, there's far too much of it. And with AI making it easier to produce even more, the volume is only going one way. 

Luke gave a pretty good example of where that can lead. He'd seen a tool where you could upload your brand guidelines and get 60 videos out of it. 

His response was basically: but for what? 

He’s not anti-AI, in fact, he uses it with his own team, particularly when they're sense-checking ideas against what they're hearing from a client's sales calls, ICP, or audience. What he hasn't seen it do is come up with the original funny idea. The human thinking still has to come first. 

And that's where the argument for comedy starts to get more interesting. A B2B brand doesn't need to turn every ad into a sketch. It does need to give people a reason to remember it when they're scrolling past hundreds of other things that look perfectly fine. 

Luke points to Ramp's Super Bowl campaign as an example. Kevin from The Office, a whole series of ads built around him, and a campaign people were still talking about afterwards. The point isn't that every B2B brand needs a celebrity and a Super Bowl budget. It's that people remember things that give them a reason to remember them. As Luke puts it, one of the biggest and most expensive mistakes you can make with your advertising is blending in. 

And suddenly, the "safe" option doesn't look quite so safe. 

Where do the jokes come from? Surprisingly, it starts with a pretty boring process. 

Every new Deadpan client starts with a kickoff session. They go through the ICP, business goals, target audience, what their day looks like, what frustrates them, and what changes once they start using the product. None of that sounds particularly funny, and that's pretty much the point. 

Luke and his team aren't sitting around trying to invent a punchline. They're looking for the thing that already feels painful or familiar to the audience, then asking how far they can push it. 

Take a recent Deadpan campaign for a fractional CMO service whose ICP is a business owner who's already been burned by a big agency selling vanity metrics instead of results. Deadpan built a campaign around a fictional gadget called The Bullshit Filter. Point it at an agency rep mid-pitch, and it forces them to say what they really mean. 

The campaign became three sketches and an infomercial styled after ShamWow and Cillit Bang. The joke works because the pain point underneath it is so recognizable. Anyone who's sat through that kind of agency meeting gets it. 

That recognition is the whole mechanism. Luke wants someone to watch, see themselves in it, and think "oh my God, that's me." Once that happens, the content creates an emotional connection that ties straight back to the brand. 

Comedy is a slightly annoying thing to analyze because you can do everything "right" and still have people stare blankly at the screen. 

Luke is pretty open about the fact that comedy is subjective. So, a campaign can land perfectly with its target audience and still get a lukewarm reaction from someone on the client team who isn't the person the joke was made for. 

So how do you know for sure when something is funny, and when everyone involved is trying very, very hard to make it funny? For Luke, it comes down to understanding the audience, knowing the tone, and knowing how far you can push a joke before it stops feeling true. 

He saw what happens when that groundwork isn't there on a project Ahrefs did with another video company before Deadpan. The video looked expensive, but it just wasn't funny. Ahrefs' CMO had raised concerns about the script while they were making it. The response was essentially: don't worry, we'll fix it with improvisation on the day. 

They didn't. 

For Luke, that's the difference. Good B2B marketing humor begins with the funny. That doesn't mean improvisation is bad. In fact, quite the opposite. Some of Deadpan's strongest moments have come from improvisation on set. 

The difference is what you're improvising on top of. 

• You understand the audience. 
• The idea starts with a real pain point. 
• You know how far you can push the joke before it stops feeling true. 
• The script gives the actors enough groundwork to improvise from. 
• Someone can riff on the day because the thinking has already been done. 

• The script isn't working, so you hope improvisation will fix it. 
• The groundwork isn't there. 
• You're relying on the people on set to find the funny for you. 
• The joke starts feeling forced rather than true. 
  

The first version of the Vector campaign was a little more unhinged than the one audiences eventually saw. 

Vector helps B2B teams spot buying signals before a prospect ever lands on their website, so Deadpan took that idea literally. What if a marketer could find her ideal customer and put the ads directly in front of them? 

In the first version, she kidnapped them. Jess Cook and the Vector team liked the idea, but decided kidnapping was pushing things a little too far. So Deadpan pulled it back with the marketer still tracking down her ideal buyer, but now she just turns up at their house and makes them watch the ads. 

Slightly less illegal. 

The campaign had another smart choice built in. Deadpan used the same B2B marketer across four episodes, dropping her into increasingly strange situations as she tried to get Vector's ads in front of the right people. Once you've seen her do it once, you start wondering where she'll turn up next, and it’s a very different kind of attention than remembering a one-off ad. 

The results were hard to ignore. Branded search rose 33%, demo requests rose 22%, and pipeline rose 44%. However, the demo requests were the surprise. Luke expected the campaign to build brand awareness over time, not send people straight to a demo request form. 

The reason came down to one edit. Early versions of the ads had a 35-second voiceover explaining how Vector worked, turning the end of the ad into a mini product explainer. Jess cut it, keeping only the line "the next best way is Vector" and dropping everything after it. That left people with a question instead of an answer, and if they wanted to know more, they had to go find out themselves. 

That edit gave the Vector team confidence to keep pushing the idea further, which is where the sitcom-style Series A announcement video came in. You can see the full campaign, including the ads themselves, in Deadpan's case study on the Vector campaign. 

The objection is rarely, "This isn't funny." It's more likely to be, "But will this work for us?" 

Luke starts getting a feel for that before they get into the campaign ideas. In the kickoff session, he'll ask about brands the client likes, show them a few examples, and see what gets a reaction. Then Deadpan comes back with three or four campaign directions, from fairly safe to completely unhinged. They don't tell the client which one to choose. 

Inevitably, the client asks Luke which one he'd go for. He has an answer, but it isn't always the wildest idea on the page. 

A lot depends on what everyone else in the category is doing. If the competitors are all playing it safe, a client doesn't need to go completely unhinged to stand out. Being the brand that's willing to have a bit of fun might be enough. But if everyone else has already started doing that, the safe option isn't really safe anymore. It just puts you a step behind. 

And the idea isn't locked in once the client picks it. Deadpan can push it further or rein it back depending on how the client feels once they see it coming together. For Luke, getting a client comfortable with risk isn't about persuading them to be brave. It's about giving them a better way to judge what "safe" really means. 

Comedy depends on timing. It could be anything from a look to a pause, or even the way someone delivers a line. So what happens when you take that carefully constructed moment and turn it into a LinkedIn post or a GIF? 

Luke's experience is that it can work, but it depends on how you built the campaign in the first place. 

If you take a still from a comedy ad and drop it into an email or onto LinkedIn on launch day, there's a good chance nobody knows what they're looking at. The audience hasn't met the character or seen the joke yet, so there's no context. 

That's why Deadpan's sitcom approach works so well for this. Once the campaign has been around for a while, people know the characters and the world you've built around them. A GIF or a still can then work on its own because the audience already knows what it's part of. They don't need the whole 30-second ad to get the joke. 

And there's a lot to work with. Four episodes can turn into more than 50 video assets once you start cutting different versions, formats, shorts, and intros for testing. Add the stills and GIFs pulled from the footage and, as Luke puts it, you're getting closer to 100 assets. 

The point isn't to make 100 things for the sake of it. It's that comedy is unpredictable, so you don't know in advance which joke, character, or cut will hit hardest. 

Vector was a good example. The ad that performed best online wasn't the one that performed best on CTV, and it wasn't even Luke's favourite of the four. The audience gets the final vote. And when you've built a campaign with enough material to give them options, you're in a much better position to find out what they like. 

Not every brand needs a four-episode sitcom to find out if comedy works for them. Luke's answer for where to start is a lot smaller: make a meme. 

It costs nothing but time. Find something true about your audience's world, something that makes light of a real pain point, and see if it lands. Post it, or send it to a few people and watch how they react. A laugh, a share, someone tagging a coworker in the comments, that's a signal worth paying attention to before spending real budget to find out the hard way. 

Luke pointed to the Truman Show meme trend as a missed opportunity. Plenty of brands jumped on it. Almost no B2B brands did, despite it being one of the easiest formats to adapt to any audience. Spotting a trend already doing the rounds and finding the angle that fits your ICP is, in Luke's words, about as low-effort a way to test comedy as it gets. 

One meme won't turn a brand into a comedy account, and it doesn't need to. It answers a single question: does this audience respond to us having a sense of humor at all. For most B2B marketing teams, that's a cheaper question to answer.  

If you want to see more brands doing comedy well right now, Luke would point you to Claude, Liquid Death, Eat Surreal, and Airwallex. 

His approach isn't really about being funny for its own sake. It's the same discipline behind any serious campaign, know the audience, find what's true for them, then decide how far you can push it. Comedy just happens to be where that thinking leads if you follow it far enough. 

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