In Ask5: Building the Apprenticeship Pipeline: From Pre-Apprenticeship to Career Pathways with Aileen Alyward, Aileen shared her nonlinear career journey—spanning education, teaching, public health, social work, and workforce development— and how that shaped a meaningful career focused on expanding opportunities for others. The conversation highlighted the value of embracing career transitions, lifelong learning, and remaining open to new experiences.
The discussion also explored CareerWise New York’s mission to strengthen career pathways through apprenticeships and work-based learning, emphasizing the importance of collaboration among employers, educators, and community organizations. The session concluded with insights into building healthcare talent pipelines and practical advice for adult learners, career changers, and anyone interested in pursuing a rewarding career in healthcare.
Bio: In her role as Healthcare Pathways Integration Manager, Aileen works with stakeholders to strengthen CareerWise New York’s growing set of pathways for healthcare careers. Bringing people and organizations together to solve complex challenges has been a throughline in Aileen’s work. Prior to joining Careerwise, Aileen worked with healthcare institutions to lead cross-sectoral partnerships to address unmet community needs. Her experience includes implementing social needs screenings in clinical settings, coordinating grant-funded research studies, and facilitating multidisciplinary stakeholder teams to respond to cases of elder mistreatment across New York City. Aileen received a BA in English and Government from the College of William and Mary, and completed an MSW-MPH degree at the University of North Carolina at Chapel Hill. She spent several years teaching English as a Foreign Language in Austria and Germany, observing the array of pathways to career and technical education embedded within these nation’s schools systems. Outside of work, Aileen recharges by running around New York City, exploring parks and museums with her family, and reading good books.
