Pineapple sold itself by admitting nobody had heard of it

Pineapple, founded in 2017 as an app-based short-term insurer in South Africa, arrived with essentially no brand recognition in a market sternly dominated by established names — Santam, Discovery, OUTsurance — whose advertising spent decades projecting heritage, scale and confidence to manufacture trust. Insurance is also a category consumers dislike buying: it is complex, sold on fear, and its marketing is the most distrusted in the sector.

A conventional entrant would have answered its liability — 'nobody has heard of you, and this is a product built on trust' — by out-spending the giants on trust-building campaigns, emulating their confident tone until shoppers stopped noticing it at all. That route demands a budget a startup does not have, and even if funded, it never removes the category's real blocker: people simply do not love insurance.

Halo's campaign '100% Pure Results' made the brand's obscurity and the category's unpopularity the entire message. Instead of pretending to heritage, the billboards openly confessed weakness in slang-savvy, self-deprecating lines — 'Never heard of Pineapple? Honestly, same' — and low-cost honesty aimed at a digital audience that does not love insurance. When one tongue-in-cheek billboard drew a regulatory complaint, Pineapple even sold the ensuing confusion and reprimand as the next campaign: 'Any PR is good PR? No? OK.'

Confessed its obscurity and the category's tedium in self-deprecating billboards, making sincerity a tactic incumbents can't copy without confirming distrust.

Confessing weakness breaks the expected corporate script, so it reads as honest.

In a category built on suspicion, the brand that admits a flaw becomes believable.

The audacity is shareable, multiplying a small ad buy into earned attention.

Incumbents can't copy sincerity without confirming distrust, so they're boxed in.

When you can't out-spend incumbents on trust, name the truth they can't admit and make it your ad.

Won Grand Effie SA 2024 and turned a regulator's reprimand over one billboard into the next campaign; growth figures self-reported The Advertising Appeals Committee's overturn of the ARB's offence ruling set a precedent that a confused or missed joke is not a Code breach, and the frankness proved durable — the honest voice is still running in 2025 campaigns and Halo was named FM AdFocus Agency of the Year for the work