Cassandra Madison to discuss AI as Connect 351’s Saturday keynote

Cassandra Madison, a technology leader who helps public officials understand and engage with digital innovation, will explore the promises and challenges of integrating artificial intelligence into municipal government as Connect 351’s Saturday keynote speaker on Jan. 24 in Boston.

Amid rapid advances in AI over the past few years, municipal governments are grappling with questions about how the technology will shape the future of public services. Madison, who is executive director of the nonprofit Center for Civic Futures, has spoken to municipal leaders in other states, including at a Maine Municipal Association conference, about AI’s implications for how city and town halls will function going forward.

“Local governments are carrying immense responsibility with limited capacity, and AI offers an opportunity to transform how they serve the public,” Madison told the MMA. “But for that transformation to take root in ways that strengthen public service, leaders themselves must experiment, learn, and get their hands on the technology.

“Doing so will make them more discerning consumers of AI and better positioned to shape what happens next — how this technology is used, and how it impacts the communities they serve,” she said.

A nationally recognized leader in public-interest technology, Madison has two decades of experience in helping government deliver services with integrity and empathy while using modern tools. Through her background working both in government and alongside it, she said she has learned how to turn policy into practice, guiding the design and implementation of public systems that are effective and respond to people’s needs.

At the Center for Civic Futures, Madison and her team work to give government leaders the tools and expertise they need to make thoughtful decisions around the use of AI and other emerging technologies. The center operates on the idea that if public officials manage the risks of generative AI and other technologies prudently, they can significantly enhance the ability of governments to serve the public.

Madison was previously vice president of partnerships at the Tech Talent Project, where she worked with federal, state and local government agencies to expand their capacity for hiring technology talent. In the course of five years, she said, she was able to help more than 100 tech leaders transition from roles in the private sector to government service.

Madison has also worked for the state of Vermont, where, as deputy commissioner for the Department of Health Access, she led the turnaround of the state’s Health Insurance Exchange and Integrated Eligibility System.

Madison was involved in the digitization of Vermont’s eligibility determination process for public benefits, allowing residents to photograph their paperwork and upload instead of having to mail it or, in some cases, drive significant distances to submit their documentation in person.

Madison is also co-founder and CEO of Madison Insights, a consulting practice that helps mission-driven organizations build the teams, infrastructure, and capacity to deliver technology that improves lives. She is a senior advisor to the Federation of American Scientists and the Aspen Institute’s Financial Security Program, and serves as an independent board member at AidKit. She has a bachelor’s degree in political science and women’s studies from Penn State University, with a minor in information sciences and technology, and she is a former non-resident fellow at New America’s New Practice Lab.

“I’ve seen firsthand how fragile trust in government can be when technology fails,” she told the MMA recently, “and how powerful it is when technology truly serves people.”

Madison now works to help demystify AI and other technologies, and to show government leaders how the thoughtful use of these tools can help transform public service.

“Helping municipal leaders understand AI isn’t about chasing hype — it’s about giving them the confidence, tools, and wisdom to shape the future in a way that reflects their communities’ values,” she said. “I believe that when local leaders are empowered, they can set precedents that ripple outward and redefine what public service looks like in the age of AI.”