The Workplace Innovation Now (WIN) AI Challenge is seeking bold solutions that address the impact and potential of AI in quickly evolving workplaces, from AI-powered solutions that help support women at work, to AI skill-building and solutions that mitigate bias in AI.
When women succeed in the workplace, we all win. Pivotal recently conducted research that shows that removing barriers for women creates better workplaces for everyone and strengthens our economy.
This initiative will source innovations that open opportunities for women’s careers, while improving workplaces for everyone and expanding prosperity for communities across the country. The workplace is where life barriers thread together, and it’s quickly transforming. Lifting these barriers and better equipping everyone to thrive in the workplace of the future can have a multiplier effect on women’s lives, their families, their communities, and the overall economy.
Lower Adoption of AI
Flexible Schedules
Employee Engagement
Fewer Women in AI Roles
Reduce Bias
WIN AI Challenge
The WIN AI Challenge is seeking a wide range of scalable approaches to leverage AI to help everyone—especially women—thrive as workplaces are rapidly transforming. This includes AI-powered solutions that help support women at work, to AI skill-building, to solutions that mitigate bias in AI.
Solutions will address one or more of the following barriers. Review “The Challenge” section in the read-only application to determine which barrier your application will address.
- Limited AI tools supporting workers with caregiving responsibilities. There is a gap in AI tools ready to be scaled and adopted that help caregivers thrive at work and alleviate the time required to manage work and family priorities.
- Low AI adoption rates. Women are using generative AI at significantly lower rates than men. This trend can exacerbate disparities in the workplace, including in fields with a large percentage of women such as nursing, education, and customer service.
- Limited access to AI training. The future of work will require employees to learn and deploy new AI skills, yet access to training and skills-building can be intimidating or difficult to access.
- Biases inside AI systems. We need a workforce that can identify and remove harmful AI biases as it interprets data, tests solutions, and makes decisions.
- Caregiving Responsibilities. The systems and workplaces in this country are not set up to support households responsible for caregiving such as childcare or elder care.
- The Broken Rung. Workplace practices force women into tradeoffs and competing priorities that impact their promotion and retention rates, which widen the gender pay gap.
- Inflexible Workplaces. The most powerful positions or increases in responsibility often come with the most inflexible hours and expectations. The structure of these roles can make them less attractive because they make it more difficult to balance career and other priorities.
- Violence and Sexual Harassment. Harmful acts of sexual harassment and mistreatment continue to impact women across the course of their careers and can prevent them from succeeding at work.
- Bias and Toxic Workplace Culture. Issues from burnout to unfair practices and negative assumptions can create unhealthy or hostile workplaces that hinder everyone's success.
- Salary Discrepancy. From the initial salary offer to subsequent promotions and raises, women often see less pay for their work. Industry context and intersectional barriers compound this issue and require creative solutions to break through the issue of this shortfall and deliver lasting impact.
The WIN AI Challenge is an opportunity to maximize the potential of AI to reshape the workplace to better support everyone. Research shows that AI can enable flexible work models to improve work-life balance, and can empower entrepreneurs to launch startups with fewer resources. The WIN AI Challenge is seeking solutions that lead to lasting impact—a proposal focused only on the development of a technology tool/application without a scaled adoption strategy will not likely be a strong fit for this challenge.
Join Us
The WIN AI Challenge welcomes applications from eligible organizations, such as nonprofits located within the United States and U.S. territories.
For-profit companies, government agencies, individuals, and others are encouraged to participate as part of applicant teams under an eligible Lead Organization. Potential participants are also allowed to start a nonprofit organization then apply as a lead.
All proposed projects must serve and impact communities, audiences, and/or organizations located within the United States and U.S. territories.
Please review our resources, rules and FAQ, then complete our readiness tool to help determine your fit and eligibility for the challenge.
Strong applications will focus on solutions that help everyone, especially women, thrive in a rapidly changing workplace and meet the four criteria outlined in the scoring rubric:
- Innovative: Inventive approach to build or expand an influential model that can shape other efforts, and a strategic vision and plan to efficiently scale and accelerate solutions for everyone, especially women, to thrive in a range of workplaces.
- Feasible: Solution led by innovators, seasoned experts, and/or key networks with robust experience and past results, activating rigorous evidence-based strategies and flexible plans to sustain remarkable change.
- Transformative: Powerful solution to improve workplaces and proven-effective approach to break down barriers, deliver benefits, and achieve lasting systemic change.
- Aligned: Comprehensive and impressive stakeholder alignment and thorough analysis of barriers, broader context, and on-the-ground conditions. Highly responsive solution well-positioned for success with authenticity, deep community roots, and buy-in.
The Workplace Innovation Now (WIN) Challenge is a new initiative led by the Aspen Institute and supported by Pivotal, a group of organizations founded by Melinda French Gates. It’s focused on discovering and scaling innovative ideas in the face of a rapidly changing workplace. The foundational vision, backed by research, is that when women succeed, the benefits are shared—across families, communities, and the economy at large.
Launched in 2025, the bedrock of the initiative is a $60 million grant competition open to eligible organizations, such as nonprofits in the United States. As workplaces are quickly changing, the WIN Challenge is an opportunity to find creative, actionable, and scalable solutions with forward-looking impact that address workplace barriers and support everyone—especially women—across a wide variety of industries and career phases. Successful applicants will offer a novel or breakthrough solution that nurtures the tension between innovative and evidence-based approaches.
Each of the following three WIN Challenge pillars has $20 million to support up to eight applicants who will receive a grant of either $2.5 million or $5 million each.
Culture & Practices Challenge
Seeks trailblazing, evidence-based, and scalable approaches to address the key barriers women face at work and to advance processes, standards, and norms that help everyone thrive in a rapidly changing workplace.
AI Challenge
Seeks bold, scalable solutions to address the impact and potential of AI in quickly evolving workplaces, from AI powered solutions that help support women at work, to AI skill-building, and solutions that mitigate bias in AI.
Narrative Challenge
Seeks game-changing approaches to shape new narratives that help women thrive and everyone win as workplaces are transforming. Solutions could include mitigating bias, celebrating women’s achievements in the workplace or amplifying positive and varied portrayals of what leadership looks like.
The Awards
Based on results of Peer-to-Peer Review and the Evaluation Panel, as well as other factors that may include, but are not limited to, uniqueness of solution type, geographic location, and demonstrated potential, selected members of the WIN Council will make a recommendation of up to eight solutions to receive award grants of either $2.5 million or $5 million each.
The WIN Council will be composed of noted workplace leaders, innovative thinkers, and forward-looking problem-solvers who will help guide these efforts and offer insights and big visions for what’s possible. Learn more about the WIN Council here.
Awardees will be announced in mid- to late-2026. Each awardee will enter into a direct and separate grant agreement with the Aspen Institute and will be required to report progress towards milestones and other goals.
In mid-2026, Aspen Digital will host a summit to uplift the solutions and changemakers sourced through the WIN Challenge. The knowledge curated will be shared widely across industries, the philanthropic community, and decision-makers committed to reshaping workplaces with forward-looking ideas so everyone can thrive. In the final year of the WIN Challenge initiative, Aspen Digital will focus on providing programming for the awardees and supporting their journey.
