The "Sitcom" Ad Strategy: How One Funny Video Closed 12 Deals | Luke Winter (Deadpan Agency)

One of Deadpan Agency's comedy campaigns paid for the entire production cost within a single episode — and went on to influence 12 additional client deals. Luke Winter didn't get there by making polished corporate videos. He got there by making B2B brands funny.

Luke is the founder and creative director of Deadpan Agency, a London-based studio specializing in comedy video for SaaS and tech companies. After 12 years producing the kind of cinematic explainers that collect 400 views and disappear, he pivoted to a niche within a niche: episodic B2B comedy campaigns built around real customer pain — not brand ego.

You'll learn why humor lowers purchase resistance better than any production budget, how the StoryBrand framework keeps your brand from accidentally casting itself as the hero (and why that's the wrong move), and what actually happens to your brand when a joke doesn't land — the answer is less catastrophic than you'd expect, but bad audio is a different story entirely. This is also why AI can generate a video but can't replace the taste to know if it's any good.

(00:00) Intro
(01:15) Why B2B brands invest in video ads
(03:48) What a comedy video campaign actually costs
(08:35) Why humor outperforms spectacle in B2B marketing
(14:08) How to measure if a video campaign worked
(21:13) How to make the humor feel owned by your brand, not your agency
(25:07) Rooting comedy in real customer pain
(28:12) The StoryBrand secret: your brand is the guide, not the hero
(32:21) How to build a visual identity audiences recognize across episodes
(38:21) What actually happens when a video flops
(46:21) AI-generated video: useful tool or creative shortcut?
(52:33) Why taste matters more than the prompt

Where to find Luke:
LinkedIn: linkedin.com/in/luke-winter-75a2885a
Website: deadpanagency.com

Where to find Tim:
LinkedIn: linkedin.com/in/timsoulo
X: @timsoulo
Website: timsoulo.com

Referenced:
Deadpan Agency: deadpanagency.com
Gamma: gamma.app
StoryBrand by Donald Miller: storybrand.com
Contagious by Jonah Berger: jonahberger.com/books/contagious/
ClientBoost: clientboost.com
Ahrefs: ahrefs.com