The Founder Files Pineapple's Genius Strategy to Disrupt The Insurance Industry - Ndabenhle Ngulube, Pineapple
Pineapple Insurance has taken the South African insurtech space by storm, and today, we’re diving deep into their journey with co-founder Ndabenhle Ngulube.
From their viral marketing campaigns to their unconventional branding strategies, we explore how Pineapple carved out a unique position in the market. Ndabenhle shares insights into their customer segmentation, growth strategy, and the genius behind their long-term vision.
We also break down how they scaled to a 215-person team, the evolution of their company structure, and how they use OKRs to drive execution across all levels. Plus, the challenges of building a strong middle management team—and much more.
This episode is packed with actionable insights for any founder looking to scale fast and stand out.
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This episode is brought to you by Metavolve.
Metavolve turns highly capable African founders into confident business leaders by helping them develop clear and comprehensive business strategies that make building a great sustainable business less complex. Reach out to our team to learn more:https://metavolve.co/
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00:00 Introduction
03:06 What is Pineapple?
07:21 The Founding Story
12:16 10 Questions to Ask Yourself About Your Customer Experience
14:59 Ndabenhle’s Super Power
21:14 Buying 60k Pineapples for the New Product Launch
25:41 What Scale is Pineapple at Right Now
28:08 Making Insurance Affordable for Lower-Income Individuals
37:10 The Genius Growth Strategy Allowing Pineapple to Take Market Share
59:11 Managing Company Identity While Evolving Product Offering
01:06:36 Handling Competition in an Oligopoly
01:12:05 Pineapple’s Team Structure and Execution System
01:28:46 Challenges in Building Out Management Layers
01:33:27 What Does The Rest of 2025 Hold For Pineapple
01:34:57 The Future of Insurance in South Africa
01:36:41 Reflection