Roadside plantings are essential part of Okinawa’s aesthetic landscape. The landscaping industry in Okinawa has been working on digital transformation in order to increase profitability by maintaining and creating attractive landscapes unique to the island. The centerpiece of the initiative is the development of a landscaping management platform called karahai ("compass" in the Okinawan dialect), which provides an online database that visualizes every step of the workflow such as plant material production, inventory management, planting work and planting management operations. This paper provides an overview of the karahai system and the background behind its development, and presents the future prospects of the initiative.