October 8, 2026 - Empower Work and SkillUp Coalition today announced that it has been named an awardee of the $60 million Workplace Innovation Now (WIN) Challenge, receiving a $2.5 million grant to advance an innovative solution to help women thrive and everyone win in a rapidly changing workplace.
The WIN AI Challenge award supports Empower Work and SkillUp's work to blend trusted human counseling with AI-powered career navigation to help women overcome workplace barriers, achieve sustained economic well-being, and thrive.
Our Solution
Our collaborative initiative integrates AI-driven career navigation with trusted human counseling to help women navigate workplace obstacles, achieve long-term financial stability, and thrive. Core to our theory of change—that true economic empowerment depends on supporting the entire journey—this partnership addresses a major obstacle in AI coaching by embedding human expertise at scale. It combines the 24/7 availability and rapid data retrieval of artificial intelligence with the empathy, strategic discernment, and tailored guidance of experienced human coaches. Whenever SkillUp's AI identifies critical milestones, complex challenges, or emotional distress, automated triggers will seamlessly connect users to Empower Work's text- or chat-based support. Additionally, a bi-directional data flow enables both platforms to share user context, maintain ongoing memory, and continuously strengthen the support network. Learn more about our solution here.
What is the WIN Challenge?
Led by Aspen Digital, a program of the Aspen Institute, and supported by Pivotal, a group of social impact organizations founded by Melinda French Gates, the WIN Challenge was launched in fall 2025 to discover and scale transformative ideas across three key pillars: Culture & Practices, AI, and Narrative. The 18 awardees selected represent a new generation of workplace innovation, addressing challenges ranging from caregiving and workforce participation to the responsible deployment of artificial intelligence and the narratives that shape workplace culture.
Aspen Digital will spotlight the award-winning solutions at its inaugural WIN Summit on October 22 in New York City, convening leaders from business, philanthropy, academia, and the social sector to connect and learn – and to advance and scale ideas that will help women thrive and everyone win.
"The WIN Challenge started with a simple question: what would it take to build workplaces where women—and everyone—can thrive? The answer came back in hundreds of applications from every corner of the country,” said Clare Bresnahan English, Senior Director of the WIN Challenge at Aspen Digital. “These 18 awardees show us that there is no single blueprint to break down the barriers that women face in the workplace. They are all working from different angles to close the gap between what we know can make workplaces better for everyone and what actually becomes standard practice.”
The WIN Challenge received nearly 900 applications from organizations across the United States and U.S. territories with innovative approaches to help everyone succeed amid rapid economic and technological change. Each applicant underwent a comprehensive multiple step review-process, including a peer review, an external evaluation panel composed of corporate, philanthropic, academic, and nonprofit experts in workplace innovation, technology, and narrative, and a review from the WIN Council composed of distinguished workplace leaders and innovators.
More information about the WIN Challenge and the full list of awardees can be found at winchallenge.org.
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SkillUp Coalition is an innovative nonprofit connecting individuals skilled through alternative routes (STARs) with the right tools, resources and support to make confident career shifts, find quality living-wage jobs, and achieve promising career growth without the need of a college degree. Through its cutting-edge technology platform and step-by-step career guidance options, SkillUp has connected more than 5 million STARs with career, training, and job support nationwide. Founded in 2020, the coalition brings together more than 180 leading organizations, including training and education providers, technology developers, policymakers, employers, and philanthropies.
