About & Eligibility
The WIN AI Challenge seeks bold, scalable 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.
The WIN AI Challenge is one of three challenges launched in September 2025 as part of the Workplace Innovation Now Challenge (WIN Challenge), a new initiative of Aspen Digital, supported by Pivotal, a group of organizations founded by Melinda French Gates.
The WIN Challenge is an opportunity to find creative, actionable, and scalable solutions that support women in a rapidly changing workplace—and help everyone thrive—through three challenges awarding a total of up to $60 million in grants. Each of the following pillars offers a total of up to $20 million to award grants of either $2.5 million or $5 million to up to eight applicants.
- WIN 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.
- WIN AI Challenge. Seeks bold, scalable solutions to address the impact and potential of AI in quickly evolving workplaces, from AI-powered solutions that help women at work, to AI skill-building and solutions that mitigate bias in AI.
- WIN Narrative Challenge. Seeks game-changing approaches to shape new narratives that help women thrive and everyone win as workplaces are transforming.
The WIN Challenge welcomes applications from eligible organizations, such as nonprofits located and serving communities, audiences, and/or organizations within the United States and U.S. territories.
Applications that include multiple organizations and/or cross-sector partnerships are eligible. However, the Lead Organization must be an eligible organization, responsible for receiving and taking accountability for any grant funds, as well as providing overall direction, control, and supervision for the project. The selection of the Lead Organization is up to each team to determine and describe in the application.
Projects with fiscal sponsors are eligible to apply. Applicants may list both the fiscal sponsor and the project name in the Lead Organization field on the registration form (such as Project Name (Fiscal Sponsor) or Fiscal Sponsor – Project Name).
Note that educational entities must be 501(c)(3) organizations to be an eligible Lead Organization.
Applicants are also welcome to establish nonprofit entities to serve as a lead. However, if an Applicant does not have its tax-exempt status under the IRS by the time grants are awarded under this competition, the organization must have a fiscal sponsor that meets the WIN Challenge eligibility requirements to receive a grant award. Failure to secure tax-exempt status or secure an eligible fiscal sponsor will render an Applicant ineligible to receive a grant award under this competition.
For-profit companies, individuals, government agencies, and non-U.S.-based organizations are encouraged to serve as part of a team on a submission by an eligible Lead Organization. An organization can also serve as a partner on a team for multiple applications provided that each application proposes a separate, distinct solution.
Please note: Regional or location-specific branches of larger organizations, as well as departments, schools, and nonprofits within or based in a nonprofit college/university, may each register and submit separate applications naming their parent organization as the Lead Organization. Similarly, applicants may include a specific branch or department along with the parent organization in the Lead Organization field on the registration form.
In all these circumstances, the proposed solutions must be separate and distinct. There should be no overlap in personnel/team members. The intent here is to ensure that teams are concentrating their best effort into one application. Teams are encouraged to select a single project that best represents its organization's ability to deliver a solution that meets the scoring criteria.
Review the rules for more information and take the readiness quiz to help determine your eligibility and fit for the WIN AI Challenge.
Past and current grantees of Pivotal are eligible to apply. Current programs and grantees of the Aspen Institute are not eligible to apply as a Lead Organization and cannot serve as part of a team submitting the application and/or implementing the proposed solution.
Yes, for-profit and government entities are eligible and encouraged to participate, but cannot apply as a Lead Organization – these entities must apply as a partner on a proposal submitted by an eligible Lead Organization. Please review the rules for more information and email us if you have questions (and please be sure to specify the pillar(s) / challenge(s) you are referencing in the subject line of your email).
The WIN AI Challenge is seeking a wide range of scalable approaches to leverage the opportunity of artificial intelligence (AI) in a rapidly changing workplace. This could include AI-powered solutions that help support women at work, AI skill-building, and solutions that mitigate bias in AI.
The WIN AI Challenge prioritizes solutions that lead to lasting impact. Applications will focus on systemic solutions that meet the four criteria outlined in the scoring rubric and that address one or more of the following barriers:
- Limited AI tools
- Low AI adoption rates
- Limited access to AI training
- Biases inside AI systems
- Caregiving Responsibilities
- The Broken Rung
- Inflexible Workplaces
- Violence and Sexual Harassment
- Bias and Toxic Workplace Culture
- Salary Discrepancy
Proposals from organizations operating in a range of stages will be encouraged to apply. From early-stage organizations with a new idea, to existing organizations and partnerships with strong proofs of concepts or proven solutions ready to scale.
Review the WIN AI Challenge About page and “The Challenge” section in the read-only application to determine which barrier your application will address.
The WIN Challenge welcomes proposals with solutions that engage men in creating workplaces where women thrive, while creating better workplaces for everyone and strengthening our economy. Applicants will be asked to describe how their innovative idea supports working women and by extension helps everyone—families, communities, and/or the economy overall—to thrive in a rapidly changing work environment. Applicants should propose tools, strategies, and resources that are nondiscriminatory, and that help support women in the workplace without discriminating against men or members of protected categories. Applicants should not propose programs that exclude employees from jobs, promotions, contracts, or other specific employment opportunities based on their sex, race, or other protected characteristics.
Learn more here, review these resources, and please take the readiness quiz to help determine your eligibility and fit for the WIN AI Challenge.
Application Process
Before deciding whether to submit an application, we encourage you to complete this readiness quiz, then carefully review and reflect on the application requirements and scoring rubric.
Once you’ve determined you’re a strong fit for the WIN AI Challenge, register no later than 5:00 PM Eastern Time on Thursday, December 11, 2025. Registration is required and is a simple two-step process. First, create a username and password then check your inbox to confirm your registration. Next, complete the online registration form. Once you are registered, submit your application online no later than 5:00 PM Eastern Time on Wednesday, January 28, 2026.
We also encourage all participants to consider the amount of time and resources required to be competitive. Please review this read-only version of the application and word count overview in full before deciding to register and apply and note: those who submit valid applications will move on to Peer-to-Peer review where each applicant will be responsible for reviewing five applications in March — April 2026 submitted by fellow applicants using the scoring rubric. Peer-to-Peer review is required to remain eligible to move on to the Evaluation Panel.
Your submission may be shared with five of your fellow applicants as part of Peer-to-Peer Review, five Evaluation Panel members, designated members of the WIN Council, and the WIN Challenge team during the evaluation process.
All peer reviewers and Evaluation Panel judges will commit to keeping all application materials they review confidential.
Also, portions of your applications may be published online and may be shared with the general public to promote your proposal or to highlight results. Those portions may include, but are not limited to: Lead Organization, Website, Project Title, Project Statement, Executive Summary, Video Presentation, and Project Description.
The WIN Challenge recognizes that innovation emerges from novel, original ideas or a new application of an existing method. We are seeking a wide range of scalable innovations to address the impact and potential of artificial intelligence in a rapidly changing workplace.
Applications should demonstrate how the proposed solution can be scaled. Scale may mean expanding to new geographies, or it may mean how you intend to amplify your impact more deeply in one geography or context. If appropriate, explain whether and how you will need to tailor and adapt your solution for scaling and/or amplifying impact.
Applications should include evidence or reasons why the results can be replicated. The following responses may be helpful to review: 1) the article, Emerging Pathways to Transformative Scale, from the Stanford SOCIAL INNOVATION Review (SSIR) and 2) the article, The Four Pathways to Impact at Scale, from The Center for the Advancement of Social Entrepreneurship (CASE) at Duke University.
We understand that innovative solutions can reference a wide range of evidence-based practices. Applications should highlight track record, internal data, lived experience, and/or formal evidence that the proposed solution will effectively support women and help everyone thrive in the workplace.
If you do not have evidence of impact of your own solution, you should be able to point to research-backed practices on which your solution is based, or analogous solutions achieving meaningful impact that you think your solution may similarly achieve.
Award funds must be used for the project detailed in the application and may be disbursed to partners for project-related purposes as detailed in the budget.
In addition to direct project costs, the budget may include a reasonable allocation for indirect expenses associated with the overall operations of the team that are shared across the organization’s activities. A partner's indirect costs can be included as part of the total subgrant designated for that partner. We reserve the right to review and adjust amounts allocated for indirect expenses.
Award funds may not be used for the following:
- To support non-charitable purposes (see U.S. IRS definition of charitable purpose)
- To support illegal discrimination or preferences (For example, programs that exclude employees from jobs, promotions, contracts, or other specific employment opportunities based on their sex, race, or other protected characteristics. Please see About & Eligibility FAQ section above for more details.)
- To support lobbying activities or to otherwise carry on propaganda or otherwise to attempt to influence legislation as defined under the tax laws
- To influence the outcome of any specific public election or to carry on, directly or indirectly, any voter registration drive as defined under the tax laws
- To engage in any activities, such as administrative lobbying that is not necessarily treated as lobbying under the tax laws but could be subject to public disclosure under federal, state and/or local laws
- To support activities (a) prohibited by US laws related to sanctions and combating terrorism; (b) with persons on the List of Specially Designated Nationals (www.treasury.gov/sdn) or entities owned or controlled by such persons; or (c) with or in countries against which the U.S. maintains comprehensive or targeted sanctions, unless such activities are fully authorized by the U.S. government under applicable law and specifically approved by Competition Sponsor in its sole discretion
- To support any activities which do not comply with anti-corruption laws, regulations, and ethics standards that apply to government officials, including but not limited to payment to government officials
- Funding or grants to any organization not related to the proposal, to any individual for travel, study, or other similar purposes, or to make a grant to any organization that is not a Section 501(c)(3) public charity, except in compliance with the provisions of Sections 4945(g) or (h) of the Internal Revenue Code, as the case may be
- Creation of any endowment or for the aggregation of philanthropic capital by organizations that regrant to nonprofit organizations
- Creation of a venture capital fund, or pooled funds to invest in or distribute to for-profit organizations
- Loans or microloans to individuals, nonprofits, or for-profit entities
- General operating support for the Lead Organization and/or any partners (see Section 7 of the rules)
- Funding 501(c)(4) organizations or 527 political organizations
- Government services
Yes, you may submit an application to one or more of the three WIN Challenge pillars. Please do not submit the same application for all three challenges—each application should demonstrate why the proposed solution is a strong fit for the focus of each challenge. Learn more about all three challenges at winchallenge.org.
An organization may only serve as a Lead Organization on one application for each of the three challenges. An organization may be a partner on more than one application if each one proposes a separate and distinct solution. And each application must be submitted by a different, eligible Lead Organization.
Please note: Regional or location-specific branches of larger organizations, as well as departments, schools, and programs within or based in a college/university, may each submit separate applications naming their parent organization as the Lead Organization on their applications. Similarly, applicants may include a specific branch or department along with the parent organization in the Lead Organization field on the registration form.
In all these circumstances, the proposed solutions must be separate and distinct. There should be no overlap in personnel/team members. The intent is to ensure that teams are concentrating their best effort into one application. Teams are encouraged to select a single project that best represents its organization's ability to deliver a solution that meets the scoring criteria.
All proposed solutions must be implemented in the United States or U.S. territories. Applicants have the opportunity to select and describe the type of communities, audiences, and/or organizations that will benefit from the proposed solution (see Section F. Beneficiaries & Impact on the application).
Evaluation Process
Once the submission deadline passes, the WIN AI Challenge team will perform an administrative review to confirm each submission meets the rules and application requirements before advancing to Peer-to-Peer Review.
Peer-to-Peer Review will result in a rank order of all valid submissions. Applications that advance to Peer-to-Peer Review will be scored by five fellow applicants. Based on the rank order of scores, a selection of top-scoring applications will move forward to the Evaluation Panel.
Peer reviewers and the Evaluation Panel will use the scoring rubric to provide scores and valuable feedback on their assigned submissions, and all scores will be statistically normalized to ensure fairness. Applicants that advance to the Evaluation panel will be reviewed by five judges.
The WIN AI Challenge team will review the top-scoring submissions resulting from Evaluation Panel review to select top-scoring applications for consideration by designated members of the WIN Council. Based on considerations that may include, but are not limited to, Evaluation Panel resulting rank order, organizational capacity, geographic impact, and demonstrated potential, the WIN Council will recommend up to eight awardees to receive grants of either $2.5 million or $5 million each. If a WIN Council member has a conflict of interest with any Applicant, such Council member will recuse themselves from reviewing such Applicant’s proposal. Final decisions and selection of awardees will be made by Aspen Digital.
To help ensure a level playing field, we publish a readiness tool, the full application requirements, word count overview, scoring criteria, and evaluators to help ensure any visitor to this site has the information needed to participate.
All applications that pass an objective administrative review will move on to Peer-to-Peer Review, a feature of this grant competition that aligns with our broader goal of fostering a culture of collaboration and helping to ensure the process includes input from those closest to the work. It allows participants to provide feedback on ideas from other teams with different perspectives working toward a similar vision. It also exposes each participant to other teams who aim to achieve the same goal.
The WIN Challenge team will review the results of Peer-to-Peer review–including the feedback applicants provide– to select applications to move on to the Evaluation Panel. Peer reviewers are encouraged to provide the kind of quality, helpful feedback they would wish to see on their own application to help inform the WIN Challenge Team’s decisions.
Once review is complete, all scores will be statistically normalized to account for reviewers who are naturally more lenient versus those who tend to score more harshly. This will ensure that an application that might be assigned to a reviewer who tends to give low scores is not disadvantaged and an application that has a reviewer who tends to score high is not favored.
Unfortunately, due to the anticipated high volume of submissions, we will not have the capacity to provide reviewer feedback to applicants.
General & Technical Support
Your work saves automatically and the status of your application is available to view on your dashboard.
You have the option to request an automated confirmation email after clicking Submit – be sure the checkbox is clicked to opt into this email when the confirmation message appears.
The platform works best when using Google Chrome as your browser on a laptop or desktop computer, with view zoom at 100%.
Once you complete the registration form, you will have access to the Forums and online application.
Please email all questions and requests for technical support to questions@winchallenge.org and include the pillar(s) to which you are applying in the subject of your email.
We will also host a Q&A webinar for anyone interested in the WIN Challenge, sign up details will be announced on News. On this webinar, we will provide an overview of the WIN Challenge and process, and answer questions.
Please note: To ensure fairness for all our participants, the Carrot, Aspen Institute, and Pivotal teams cannot take phone calls or meetings, and we are not able to provide guidance that is very specific to your proposed solution or team structure. Please refer to the information on this website for more information and consult with your legal / tax professionals as needed.
