Reaching the ever-elusive tech audience in an authentic new way

Pluralsight wanted to reshape the perception of their brand and grow awareness of it. Our strategic work was built around truly understanding the desires of tech workforce leaders, along with the solutions that truly mattered. That meant deep research and rapid collaborative ideation through workshops.

A woman standing next to a colorful spinning wheel, pointing towards it with a smile. The wheel has various tech-related terms written on its segments.
Image of a film crew on set, filming two actors for an iteration of the 'Shoulda Seen It Comin' ad campaign.

A different methodology for a unique campaign

With our clients wanting something fresh and the tech/developer audience’s abhorrence for traditional advertising, we had to reimagine how a campaign could look. This led us to a creating a mockumentary series that was both absurd and relatable at the same time. Each episode championed one of our core RTB’s without ever feeling like you were watching an ad—which was exactly the point. View the work at

Three promotional images for Pluralsight, each featuring different scenes and text.  The first image shows three people reacting in surprise while looking at a laptop. The text reads, "Don’t fake it till you break it" with a subtitle "Shoulda Seen It Comin’ - Season 2 now on Pluralsight."  The second image depicts a man and a woman looking at a computer screen with concerned expressions. The text reads, "Don’t make the same mistake once" with a subtitle "Shoulda Seen It Comin’ - Season 2 now on Pluralsight."  The third image shows a woman presenting in front of a screen with charts, while a person sits on a couch nearby. The text reads, "How to upskill for a downturn" with a subtitle "Shoulda Seen It Comin’ - Season 2 now on Pluralsight."  Each image has a "Learn More" button and additional text below, describing Pluralsight's offerings and benefits.

With 10 episodes throughout two seasons of the Shoulda Seen it Coming campaign in the books, this has become the most successful campaign Pluralsight has ever run. The stories and creative resonated with the audience and showcased the brand and its benefits in a whole new light.

Image of a man slouching in a work call booth, eating noodles from a takeaway box.
Three individuals covering their ears in a red room due to loud music, while a man in the background appears incredulous.
A quote by Lee Anderson: '...the fact your adverts are on during Parks and Recreation on Freevee, and how absolutely seemless they are that l don't [realize] the transition is amazing."
A man standing near a maintenance closet with a post-it reading "Carl" on it, looking out suspiciously.

‘The experience that I've had over two years of working with Designt is like... I'm working with great people. I trust them with my brand, I trust them with my money, and it's a partnership that is empathetic, is adaptive, and is fun. To see that play out and how intricate and nuanced [the work] is, really speaks to the level of craft and intentionality that this entire team shows. And the success that we've seen, it's why we've maintained the relationship.’

Adam Gunn

SVP of Brand, Pluralsight


2.2M Clicks

146M Video views

1.01M Page sessions

703M Impressions






Project team

Stefan Hajek

Patrick Halferty

David Walsen

Veda Nagpurkar

Jaime Diskin

Brett Bollier

Ellen Hafer

Scout Shannon

Kathryn Orr

Nicholas LaManna

Andy Schwartz

Richard Kanichuck

Jacquie Bailey

Derek MacLellan

Michael Newsome

Syndney Fullerton

Colby Wayne

Rich Gonzales

Erik Wagner

Simone Rego

Andrea Bermúdez

Julianne Andersen

Kevin Zwier

Kin Lok

Zach Hoedl

Benny Haryanto