The Swiss Energy Strategy 2050 implies a transformation of the provision of thermal energy services (heating and cooling) to become CO2 neutral, district heating and cooling (DHC) are an important solution, which is technically challenging to design and whose implementation entails certain risks for investment. The GENEAP (Geospatial Analysis and Planning) project developed a software that applies automation and digitalisation to address this barrier and to apply scientific research to support the work of practitioners. The software Thermal Energy System Simulation Assistant (TESSA) increases reproducibility and decreases errors, and thereby reducing overall costs. We introduced innovative algorithms for modelling heat and cooling demand, thermal energy supplies, and the cost of thermal network technologies under different retrofit and climate change scenarios. We developed graph theory-based algorithms for computationally efficient routing of thermal network pipes. The goal of the GENEAP project was to validate the models and to establish how practitioners would find value in such a tool. Through workshops and interviews we established the need for digital tools due to the rapidly increasing need for new projects, the complexity and long time frames of projects, and the limited number of available experts to do this work. We found a gap between the high level energy strategy (Plan Directeur Energetique) and the detailed engineering design stage. In between these two stages we find the need for a flexible approach that can integrate cities and societies needs into the engineering design with non-energy requirements (e.g. political context, urban constraints and opportunities, etc).