Making fun and interesting marketing campaigns can be a challenge — especially if you are an insurance company. This is why Saads Abrahams from media update is exploring Pineapple Insurance's marketing perfection!
Anyone in South Africa can mention at least one Pineapple insurance billboard that has made them either giggle or scratch their head. Pineapple has done something that many brands, especially insurance brands, have not been able to achieve — be memorable.
Pineapple has created multiple Out-of-Home (OOH) billboards, and some of them have been so brilliant that they've been going viral, online and in person — I've personally had a few conversations discussing Pineapple's adverts.
Quirky Advertising
Some of Pineapple's first OOH campaigns used a lot of Gen Z and Millennial slang, and to some this might be odd, but if you think about it, these are the generations that are now buying insurance.
Why does this work? It makes Pineapple look approachable, and it also presents itself as a brand that understands how we think, speak and act. And for an insurance company, this is a brilliant strategy.

Business Day
In December of 2024, Pineapple revealed a new set of December-vibes billboards. These billboards stood out compared to almost every other festive billboard that was up. And the reason for this was because they were unexpected, funny and relatable.
Which we can see is the theme that Pineapple has been sticking to — and understandably so, it was working for the brand.

Instagram
And then, Pineapple launched its next OOH campaign. This campaign consisted of billboards using short, punchy lines — which were interesting but mostly confusing. Many people were discussing them online and in person, trying to understand what on earth most of the billboards were saying. Proving that not every quirky and out-of-the-box idea is a great one.
Instagram
Pineapple then did something unexpected; it addressed the confusion on its social media pages — but not in a normal business professional manner. In the quirky, humorous way that it has always been presenting itself.
And that is incredibly important; even in a marketing fumble, by sticking to its brand's tone of voice, it is solidifying its brand image.
Instagram
After it addressed the confusion online, Pineapple had a brilliant idea to take it to the streets by "covering up" the existing billboards with text poking fun at its failed OOH campaign. It also changed the tagline from "Life hard. Insurance not." to "Advertising hard. Insurance not."
By doing this, Pineapple was able to turn its advertising flop into a success, continuing with its original strategy of being funny, unexpected and relatable.
LinkedIn
Why It Works
Most marketing we see today is very predictable and safe — and then you get brands such as Nando's that constantly push the boundary on funny but controversial topics.
Pineapple knew that as an insurance company, it needed to do something different to stand out in a sea full of insurance companies, and by using the language and humour that the younger generations use, it has been able to successfully build a brand that almost every South African knows.
What are your thoughts on Pineapple's marketing? Let us know in the comments section below.
*Image courtesy of Pineapple