The flexibility of digital learning environments allows for personalized content delivery tailored to individual teachers’ needs, fostering active and engaged learning. The opportunities offered by these digital technologies can help teachers adopt a lifelong learning attitude, which has become necessary to maintaining high educational standards in line with international guidelines and policy. However, teachers often struggle to leverage these digital technologies and integrate them in their daily activities. To overcome this problem, we developed a custom-built webinar training course focused on enhancing distance learning teaching in a flexible environment. We tested this training course on a group of 197 primary school teachers and examine the relationship between learning goal orientation, motivation, and intention to transfer and how they related to teachers’ personality traits. We found that our webinar training course is easily implementable and valued by teachers, who highlight the importance of allowing the choice between different training levels. The data analysis indicates that intention to transfer is predicted by learning goal orientation and motivation. In conclusion, the study emphasizes the importance of flexible learning environments and tailored training programs that meet teachers’ needs and interests. From a sustainable perspective, such approaches foster teachers’ lifelong learning, enhance their professional development, nurture a growth mindset, and facilitate adaptability to change.