Empower Work & Partner SkillUp Coalition Selected As Workplace Innovation Now (WIN) Challenge Awardee
The award will advance Empower Work and SkilUp's work to help women thrive and everyone win in a rapidly changing workplace
San Francisco, California - October 8, 2026 - Empower Work is honored to be named an awardee of the $60 million Workplace Innovation Now (WIN) Challenge, receiving a grant for our partnership with SkillUp Coalition to scale an innovative solution to help women thrive and everyone win in a rapidly changing workplace.
The WIN AI Challenge award supports a new initiative: Beyond the Barriers: AI+Human Support to Advance Women’s Workplace Equity. Over the last two years, Empower Work and SkillUp have partnered to bring our navigational support to people and communities who need trusted career support. With the WIN AI Challenge, Empower Work and SkillUp will integrate deep human connection with AI-enabled career navigation to deliver just-in-time support, warm handoffs to counselors for complex issues, and structured AI follow-up with personalized next steps. By combining human judgment with scalable AI, this model turns moments of uncertainty into sustained action—strengthening agency, reducing barriers, and ultimately improving women’s financial and emotional well-being.
“The time is now to build what we know communities need: support that truly meets people where they are when they’re facing a speed bump - or a cliff - in this current economy,” Jaime-Alexis Fowler, Founder & CEO of Empower Work said, “We're thrilled to do this important work with SkillUp and to test and learn together in ways that can positively impact not just those we directly support, but the wider ecosystem. This initiative will create seamless experiences for those making decisions about their careers, ensuring everyone gets support at the moment they need it. Across the more than 600,000 people we’ve supported, we know how game-changing that can be. For those who get support on the text line, 92% report improved mental health and a year after support people report an average of $8,500 in economic gain vs. data that shows that those who experience harm at work often see negative impacts emotionally and economically. Empower Work ensures everyone has a resource at their fingertips, and have actionable next steps to improve their situation.”
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.
Empower Work is a national non-profit that envisions a world where everyone can thrive at work. When work actually works for people, every individual’s economic and emotional well-being increases. And there is a ripple effect: communities, companies, the economy, and our democracy, thrive.
We meet people in real time, at the exact moment they need help at work—providing support right at their fingertips. Through the power of technology, trained peer counselors provide immediate guidance on any work issue via our text line. Empower Work’s wraparound support also includes strategic partnerships, human-centered technology, and accessible online resources. Since launching in 2018, we’ve supported over 620,000 workers, with 92% reporting improved mental health and an average 32% increase in income within a year after connecting with a peer counselor.
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Founded in 2020, SkillUp Coalition is a 501(c)(3) nonprofit career platform that enables job seekers to break into high-growth careers without the requirement of a college degree. SkillUp provides direct access to a pre-vetted pool of millions of STARs (Skilled Through Alternative Routes) nationwide. Partnering with a vast ecosystem of employers, training providers, and community organizations, SkillUp delivers free career discovery tools, training referrals, job application guidance, and personalized coaching to help non-degree workers secure living-wage jobs and achieve economic mobility.