Distance-based graduate education programs in technology and related disciplines (e.g., aviation) are rapidly expanding; a cornerstone of these professional programs includes proper education in statistical analysis. A unique consideration of such programs is their primary focus on professional students – those who intend to pursue industry careers rather than a role in academia. For these students, a thorough grasp of the practical application of statistical analysis and statistical software tools is essential; however, conventional graduate statistics teaching methods are ill-suited to this audience. The author, who has won university-level awards for teaching statistics via distance technologies, discusses the challenges and strategies facing instructors and students in a technology-mediated educational environment. The role of statistical software tools for applied learning is evaluated, and available learning technologies are explored.