Pineapple saw existing insurance models, user journeys, and products as inadequate and sought to improve them in the following ways: 1) Restructuring the business model to align incentives, demonstrate how premiums are utilized, and give members a portion of their premium back; 2) Utilizing AI to make insuring as simple as taking a picture and providing coverage in under 60 seconds; 3) Offering per-item insurance and introducing new products to cover areas otherwise unavailable or inaccessible to many. In 2018, Pineapple launched in South Africa with their "My Stuff" per-item insurance, followed by their "My Ride" auto offering. Additionally, they have partnered with Travelers in the US and white-labeled their platform in the US.