The advisory services play a pivotal role in addressing the challenges of the European green transition and enhancing the quality of services along the organic agricultural supply chain. However, there is limited evidence regarding the role and current working conditions of professionals supporting organic farming. The present study aims to fill this gap by investigating the working characteristics and job satisfaction levels among Italian organic advisors and inspectors. The analysis of selected variables encompassing interviewee characteristics, work activities, and satisfaction metrics provides insights into the perspectives of advisors and inspectors on their roles and working conditions. The findings reveal that while technicians generally express satisfaction with their remuneration and opportunities for personal and professional growth, they also report significant stress levels and workload. Identifying variables influencing satisfaction levels was pursued to measure the association between variables. This research establishes a foundation for developing strategies to enhance the well-being and effectiveness of organic farming advisors and inspectors, thereby promoting agricultural knowledge and innovation. One potential avenue for further investigation is monitoring agricultural technicians’ operational activities at both the national and regional levels.