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Pineapple mocks insurance on 106 honest billboards — Grand Effie SA, triple-digit growth

App-only insurer Pineapple mocks itself on 106 unique billboards — 'Never heard of Pineapple? Honestly same' — honesty beats price ads, Grand Effie SA

Pineapple

The ideaSay the quiet part: 106 billboards, each a self-deprecating joke about insurance — 'Never heard of Pineapple? Honestly same' — concentrated in one city until it spreadsubstantial

What it had to solve

Pineapple was an app-only insurer taking on a category built on 'switch and save' price ads. Its founder's fairness-first positioning had no voice: the young, online, meme-driven audience that openly dislikes insurance was never spoken to.

How it works

South African insurance advertising had collapsed into one-dimensional 'switch and save' price messages aimed at people already shopping around. Pineapple, a young app- and AI-based insurer, had fairness at the core of its brand but nothing to say that a distracted, meme-literate generation would hear. Its agency Halo pointed out the obvious: that generation does not love insurance, and no insurer was willing to admit it.

The campaign admitted it loudly. Instead of claiming superiority, Halo wrote 106 unique, self-deprecating headlines for 106 out-of-home sites concentrated in Gauteng — 'Never heard of Pineapple? Honestly same' being the most-shared line — betting on CEO Marnus van Heerden's 'volcano technique': one localised eruption creates more noise than a thin national spread. People remade the billboards themselves and shared them.

The commerce followed the laughter: triple-digit business growth in a tough economy, and Cape Town — where the startup had never run OOH — became one of its most successful regions simply from the word-of-mouth. In October 2024 the Effie Grand Jury named the campaign the most effective of the year, giving Pineapple the Grand Effie in the Challenger Brand Solution category, forcing a category built on fear and price to react to a brand that joked about its own obscurity.

JCDecaux Africa later documented the work as an always-on, multi-format OOH program whose data-driven site selection (car dealerships, commuter nodes) matched the challenger's meme-driven audience — evidence that the honesty platform, not a single stunt, was what moved the needle.

Why it lands

  • Honesty was differentiation: every rival claimed superiority, so openly admitting 'we're unknown too' cut through instantly to an audience that distrusts insurance marketing.
  • The volcano concentration made one market feel like a national movement — 106 jokes in a single region travelled as word-of-mouth to cities where the brand had never bought media.
  • Treating OOH as a writing craft — a unique line per site — rewarded repeat viewing and sharing, and let the audience co-create its own versions of the campaign for free.
  • Owning the insight ('you don't love insurance') let Pineapple build a brand relationship instead of joining the category's price war, which its fairness-based business model could not win.

What it did

Pineapple grew triple-digit in a weak economy; Cape Town — where the brand had never run OOH — became one of its most successful regions. The campaign was judged the most effective of 2024: Grand Effie at the Effie Awards South Africa, in Challenger Brand Solution.

VideoWatch the Effie case film

What you can take

When a category only talks to price-switchers, the audience everyone ignores can become yours by saying the quiet part out loud — self-deprecating honesty, delivered at an unmistakable scale.

Since then

Pineapple kept the voice: a follow-up entry, '100% Sustained Results: How Being Totes Honest Totes Helped Pineapple Soar', won Gold in Sustained Success at a later Effie SA ceremony, and JCDecaux Africa (June 2025) described the program as always-on, crediting it alongside the insurer's continued funding rounds and growing client base. Halo's founder Dean Oelschig capped the run by taking FM AdFocus Agency of the Year for 2024.

Sources

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