Techniques for evaluating and optimizing cybersecurity operations in an organization is disclosed. The method includes the step of providing a first set of threat scenarios to a cybersecurity operations team in a live environment and a second set of scenarios in a static environment. The response of the teams including various parameters associated it such as time taken for responding, strategies used, effectiveness of the response, etc., are recorded. Based on the recorded responses, the method further performs the step of determining overall assessment scores. Upon determining the scores, the method further performs the step of contextualizing the scores based on a plurality of parameters. Based on the contextualized scores, the method provides detailed insights and recommendations related to the performance of cybersecurity teams. Furthermore, the technique recommends modifications in processes and technology related to the cybersecurity infrastructure that directly affects the performance of cybersecurity operations personnel.