The International Conference on Software Business (ICSOB) is focused on software-intensive businesses from the Software Engineering and Information Systems perspectives. In 2023, ICSOB promoted the 2nd PhD Retreat as a one-day event in Pajulahti, near Lahti, Finland. Eight PhD students from Belgium, Finland and Sweden submitted their projects which were evaluated by three program committee members. These submissions were accepted for discussion and publication as early and mid-stage projects covering startups, requirements prioritization, artificial intelligence, hybrid work, agile software development, productivity, IT infrastructure management, green ICT, business ecosystems, sustainability, and software ecosystems. The PhD students presented their projects in two sessions in the morning after the event opening by the program committee chairs and got feedback from two experienced mentors (Jesper Andersson and Slinger Jansen). In the afternoon, students were arranged into two groups to participate in a mentorship session with four experts (Helena Olsson, Jan Bosch, Jesper Andersson, and Slinger Jansen). Finally, a motivational talk was given by Jan Bosch. We thank to the PhD students and their advisors for their paper submissions, the program committee members for their valuable reviews, the mentors for their priceless discussions, the keynote for the inspiring talk, and the ICSOB 2023 organizing committee (Kari Smolander, Sami Hyrynsalmi, and Sonja Hyrynsalmi) who assist us in the preparation of the PhD Retreat over the year. Poster and Demo Track Chairs1 Program Committee