In the business world today, customer engagement mandates creating emotions associated with real-life situations. Rapid changes and innovations are making forays into the insurance industry to make this a reality. Gamification stands at the nexus of such trends. Emerging technologies like self-service portals powered by Artificial Intelligence, Machine Learning, and Deep Learning have been trying to peek into the customers’ minds but, when it comes to influencing customer behavior, there is still a long way to go. Gamification goes a step further by applying game design thinking to non-game applications, making them more fun and engaging. It focuses on enriching digital experiences and creating several other customer-centric business models to capture customer attention. Unlike other customer engagement portals, gamified self-service portals bring fun and energy to an otherwise tedious business process. However, they collect valuable customer data in the process, using a range of appealing gaming techniques for realizing lasting business value.