Naked Insurance vs Pineapple
Naked Insurance holds the stronger position because it has raised more total capital than Pineapple, giving it a bigger financial cushion while both companies face the same AI exposure and copying risk.
Naked Insurance
Naked is a South African digital insurer selling car, home, and item cover fully online
Pineapple
South African digital insurer selling peer-to-peer style home and car cover with AI-driven claims and pricing
Dimension by dimension
| Dimension | Naked Insurance | Pineapple |
|---|---|---|
| Staying power of the core product | Naked is also rated losing its protection, selling car, home, and item cover fully online with no peer to peer twist. | Pineapple is rated as being losing its protection, same as its rival, running a peer to peer car and home insurance app underwritten by Old Mutual. |
| Exposure to AI | Naked sits at the same partly absorbed level, so AI tools chip away at parts of its offer but not all of it. | Pineapple's product is only partly absorbed by AI tools, leaving some of its value intact. |
| How easily a giant could copy them | A larger insurer or tech company could likely copy Naked's fully online model just as easily. | A larger insurer or tech company could likely copy Pineapple's peer to peer model. |
| Customer scale and market position | Naked names Pineapple's scale and pricing edge as its main source of competitive pressure, suggesting it trails on this front. | Pineapple has passed 350,000 members and is seen as having stronger price perception among digital first buyers. |
| Pressure from rivals | Naked points to Pineapple's larger member base and pricing reputation as its biggest competitive threat. | Pineapple points to Naked's faster fundraising and identical flat fee pricing as its biggest competitive threat. |
| Financial footing | Naked had raised about $31.6M cumulatively by early 2023 and added a further $38M Series B2 round in January 2025, putting its total well ahead of Pineapple's. | Pineapple has raised roughly R80 million in 2021 and R400 million (about $21.3M) by late 2023. |
Questions people ask
- Pineapple vs Naked Insurance, which is better positioned?
- Both Pineapple and Naked sit losing its protection with identical AI exposure and copying risk. Naked pulls ahead on funding, having raised more cumulative capital than Pineapple, while Pineapple leads on member numbers and pricing reputation.
- Which South African digital insurer has more funding, Pineapple or Naked?
- Naked has raised more overall, with about $31.6M cumulative by 2023 and a further $38M round in January 2025. Pineapple's raises total roughly R400 million, or about $21.3M, as of late 2023.
- Does Pineapple or Naked Insurance have more customers?
- Pineapple appears to have the larger base, having passed 350,000 members. Naked itself names Pineapple's scale and price perception as a key source of pressure on its own business.
- Is Pineapple or Naked more at risk from AI?
- Neither is fully exposed. Both are rated as only partly absorbed by AI tools, and both are seen as easy for a larger company to copy.
- Who is the bigger threat, Pineapple or Naked Insurance?
- Each names the other as its main competitive pressure. Pineapple points to Naked's faster fundraising, while Naked points to Pineapple's larger member base and stronger pricing reputation.