This report is the fourth in a series considering career-readiness factors within existing high school assessments. The primary goal of this study was to provide a preliminary validation of the career-readiness features identified in prior reports by exploring how different participant groups with different levels of experience in the career/vocational world perform on a selection of test items with high numbers of career-readiness features. Two exemplar careers, emergency medical technician (EMT) and web developer, were targeted for participation in this study. A total of 103 high school students, 111 community college students studying to become either EMTs or web developers, and 84 working EMTs or web developers participated in the study. A selection of ELA and math test items rated for career-readiness features were adapted into an 18-item test booklet. As expected, results indicated that workforce individuals scored significantly higher on the test than community college students, who in turn scored significantly higher on the test than high school students. These results suggest that having added experience in their field may lead to refining certain career-readiness skills found in high-school-level content-based assessments. Preparation for such assessments can help high school students prepare for college and/or a career, and inferences for both college and career readiness can be drawn from test performance.