Virtual Teaching Assistants (VTAs) can reduce the workload of teaching teams in Asynchronous Learning Environments (ALEs) where timely, personalized support is often limited. As VTA systems grow more capable, rigorous and pedagogically sound evaluation becomes essential. Existing assessments often rely on surface-level metrics and lack sufficient grounding in educational theory, making it difficult to meaningfully compare the pedagogical effectiveness of VTA systems. To bridge this gap, we propose a pedagogically-oriented evaluation framework that is rooted in learning sciences and tailored to asynchronous forum discussions, a common VTA deployment context in ALE. We construct classifiers using expert annotations of VTA responses on a diverse set of forum posts. We evaluate the effectiveness of our classifiers, identifying approaches that improve accuracy as well as challenges that hinder generalization. Our work establishes a foundation for theory-driven evaluation of VTA systems, paving the way for more pedagogically effective AI in education.

Understanding the gaps between job requirements and university curricula is crucial for improving student success and institutional effectiveness in higher education. In this context, natural language processing (NLP) can be leveraged to generate granular insights into where the gaps are and how they change. This paper proposes a three-dimensional research framework that combines NLP techniques with economic and educational research to quantify the alignment between course syllabi and job postings. We elaborate on key technical details of the framework and further discuss its potential positive impacts on practice, including unveiling the inequalities in and long-term consequences of education-occupation alignment to inform policymakers, and fostering information systems to support students, institutions and employers in the school-to-work pipeline.