Web-based learning (WBL) of the asynchronous type provides great potential for today’s managers and professionals to upgrade their knowledge and skills. Managers and professional staff, unlike full-time students, have to balance work, family and learning commitments. However, most research focuses on full-time students, with less concern for managers and professional staff. In this study, we adopt the ethnographic method to conduct a case study of the learning behavior and experience of managers and professional staff in an asynchronous Web-based Strategic Management course. Taking an interpretive stance, we reach several important findings: contingencies exist and influence learning behavior; deadlines play a significant but different role for different learners; learners spend more time and effort on an asynchronous Web-based course; learners adopt different strategies and build for themselves different combinations from the same set of teaching materials; and learners struggle to create for themselves a “classroom” where none in fact exists. These findings are substantial and contribute greatly to our understanding of how managers and professional staff learn in the asynchronous WBL environment.