In spite of the growing importance of software security and the industry demand for more cyber security expertise in the workforce, the effect of security education and experience on the ability to assess complex software security problems has only been recently investigated. As proxy for the full range of software security skills, we considered the problem of assessing the severity of software vulnerabilities by means of a structured analysis methodology widely used in industry (i.e. the Common Vulnerability Scoring System (\CVSS) v3), and designed a study to compare how accurately individuals with background in information technology but different professional experience and education in cyber security are able to assess the severity of software vulnerabilities. Our results provide some structural insights into the complex relationship between education or experience of assessors and the quality of their assessments. In particular we find that individual characteristics matter more than professional experience or formal education; apparently it is the \emph{combination} of skills that one owns (including the actual knowledge of the system under study), rather than the specialization or the years of experience, to influence more the assessment quality. Similarly, we find that the overall advantage given by professional expertise significantly depends on the composition of the individual security skills as well as on the available information.