Jessica Wilen is an executive coach, organizational consultant, and Yale Child Study Center faculty member who helps ambitious professionals navigate career transitions with greater confidence, clarity, and intention. She understands that parental leave is more than a logistical milestone—it’s often a profound shift in identity, relationships, ambition, and leadership.
Drawing on her background as a clinical social worker, researcher, and executive coach, Jessica creates a thoughtful, judgment-free space where clients can explore the questions beneath the surface: How do I want to lead now? What kind of parent do I want to be? How can I build a career that reflects both my ambition and my values?
Jessica has coached leaders across healthcare, higher education, nonprofit, and corporate organizations, including physicians, executives, and founders navigating high-stakes transitions. She is a Professional Certified Coach (PCC), a certified RETAIN Parental Leave Coach, and holds a Ph.D. in Social Work and Social Research.
Jessica is also a Fast Company leadership columnist and author of the Substack A Cup of Ambition, where she writes about the psychology of work, leadership, and modern ambition.