In this episode, Julia sits down with Cristóbal Durán and Derek Kitts, founders of WinFlip, to explore how AI-driven tools are reshaping the landscape of local political campaigns and what that means for nonprofits and grassroots organizers. While national campaigns often have access to sophisticated data and strategy teams, down-ballot candidates frequently operate without the same resources.

They share how the platform is working to close this gap—helping candidates better understand their districts, calculate realistic paths to victory, and make smarter, data-informed decisions without the need for large consulting teams.

The conversation also examines how nonprofits can apply these same principles to advocacy, fundraising, and community engagement—while maintaining ethical standards and trust.

💡 Key Topics Covered

• The hidden technology gap in local and down-ballot campaigns
• How AI can support (not replace) grassroots organizing
• Understanding and calculating a campaign’s “win number”
• Making campaign strategy accessible to first-time candidates
• Practical applications of AI for nonprofit leaders
• Ethical considerations in AI-driven civic engagement

💼 Cristobal Duran

Cristobal is a public affairs and communications professional focused on strengthening grassroots democracy through technology. With a Master of Public Administration from Virginia Tech and experience supporting over 500 political campaigns, he has worked across communications, compliance, and campaign strategy.

He is the founder of WinFlip, an AI-driven platform designed to help down-ballot candidates understand their districts, calculate realistic paths to victory, and make smarter strategic decisions. His work focuses on democratizing access to campaign strategy, lowering the barriers to running for office, and enabling more people to participate in the democratic process.

Connect with Cristobal on LinkedIn

💼 Derek Kitts

Derek Kitts is a retired Army veteran, entrepreneur, and elected Supervisor in Montgomery County, Virginia. With over 24 years of military service and a decade in campaign operations, he leads Tempus Leadership Solutions and co-founded Project Icarus AI, bringing innovative tools to political campaigns. His work centers on service, accountability, and helping others succeed.

Connect with Derek on LinkedIn

🔗 Resources and Links

• WinFlip Website

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