Data dreamer: Roanoke alum is now chief data officer of Illinois

Data evangelist. Force of nature. Doer, dreamer, driver. These are all ways Dessa Gypalo ’07 has been described on her path from Roanoke graduate to tech innovation leader for one of the nation’s biggest counties and states. Now, she’s adding another moniker to that list: Obama Foundation USA Leader.  

Gypalo, a Maroon honors student, soccer player and Delta Gamma, was tapped for the first cohort of a nationwide initiative created by President Obama’s nonprofit to bring together young leaders inspiring change in their communities. The invite for the 2023 program was the latest in a series of recognitions Gypalo has amassed for her work in government and civic tech.

Since 2021, she’s served as chief data officer (CDO) for her home state of Illinois, leading the charge to create systems that support stronger, data-informed resident services. Before that, she was named inaugural CDO for Chicago-encompassed Cook County, where her portfolio included building transparency-boosting open data platforms and leveraging data to guide COVID response measures.  

Her career also included work with national advocacy groups, including Enroll America, and Obama’s reelection campaign. The central thread has been the spark to seek meaningful change with and for others. “Data has to be looked at in a human-centered way,” Gypalo said. “It tells a story about people and communities. The question becomes how can we understand it better and use it to tackle the big challenges we’re facing?” 

On why she feels called to public service 

“You know, I was raised to be civic-minded. Both my parents were public school teachers, so from a young age I always knew that service and civic work were going to be part of my life. That was something that was ingrained in me.

“Now in my role here, I get the opportunity to build on those values that my family instilled in me. I have the incredible privilege of being part of moving things forward and making a change for the state of Illinois.”

On the Obama Foundation Leaders USA initiative

“Being part of this program really has been the honor of a lifetime. I can't say enough about how excited and happy I am each time we have a session and get to have these robust discussions on how to tackle big issues.

“The program was created to offer 100 leaders from diverse backgrounds the opportunity to acquire new skills and tools to drive lasting change in their communities. The focus is on strengthening institutions across sectors, so we have folks from the private sector, public sector, nonprofits, advocacy, all over, who are all working to promote participatory democracy.

“We’re learning everything from hard skills to different ways of thinking. Questions like how do we manage people and organizations through change? How do we work through conflict? How do we lead with our values and stay true to our values when we're facing conflict? We’re also talking about how we can collaborate across our different backgrounds to break down barriers and strengthen civic institutions. And how we can do it in a way that isn’t just a one-off but builds and builds and builds to realize that lasting change.”

On how data can (responsibly) change the world

“For me, data is something that is logical, but also so creative. It can tell us so much and lead us to new ideas. In my work, I want to understand how it can help us make real, lasting change for the better; how it can help organize people around a goal to take action.

“Right now, there’s a lot of news about AI, which isn’t itself a new technology. It’s been around for a while, and most of us use it in our day-to-day lives. But its power has gotten bigger, and its impact has gotten bigger. From a data management perspective, I really want to make sure that we have a strong ethical backbone as we look to the future of technology. That means thinking about how we’re using data. What are the guardrails we need? What are the privacy protections? It’s making sure that we're always looking at and evaluating the impact of what we’re doing.

“I work with other CDOs across the country, and they're all aligned in that emerging technologies, new technologies, are a net positive. Because the tech is agnostic. It's about how we use it.”

On her hope for the new generation of Maroons

“When we think about the future, I truly believe we’re all the change that we've been waiting for. That goes not just for my generation, but for the next generation.

“To the folks in undergrad right now, if you want to get involved, if you're upset about the way things are going or even if you're happy about the way things are going, get out there and make your voice heard in the civic process. Whatever that looks like — it could be getting involved in campaigns, government, advocacy organizations — anything that you can do that is really shaping what the future looks like.  

“I encourage everybody to try it at least once. It really gives you a different perspective on how the world around you works. And, more importantly to me, you get to be a part of something bigger than yourself.”