Simplesurance, established in Berlin in 2012 with a team of 150 across 30 nations, provides a one-stop insurance solution and has expanded to Japan in 2018. The Japanese market was targeted due to its high insurance penetration and digital economy, leading to the establishment of a local entity, Simplesurance G.K., to offer tailored products. The document also highlights the achievements and challenges faced in navigating cultural differences and administrative procedures during the expansion.