Field notes from the rooms where enterprise AI gets decidedNext room: Singapore & New York · 13 Nov 2026
CIO Vision
Dessa Gypalo, Head Data, Analytics, and Automation at Save the Children US
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Save the Children US

Speaker · CIO Vision Chicago 2026

Dessa Gypalo

Head Data, Analytics, and Automation at Save the Children US

1Rooms joined
1Sessions on stage
0Awards
LinkedIn

On their agenda

Four priorities, mapped against profiled leaders

01

Her core priority is establishing robust data and AI governance frameworks to turn data infrastructure into lasting organizational capability. She focuses on ethics

AI strategy
03

Breaking down data silos

04

And driving AI value by requiring business teams—rather than IT alone—to own operational outcomes and ROI.

AI strategy
Source: 734 CIO Vision leader profiles with at least one priority theme, from 742 leaders in the series. Share of those leaders in each theme; leaders may have multiple themes. Yellow marks Dessa's saved themes.

In the room

Chicago, 21 Aug 2026

See the full Chicago room
Chicago room · 21 Aug 2026
Chicago · 21 Aug 2026
Chicago room · 21 Aug 2026
On film

CT · Panel

Beyond the Business Case: When Does AI Investment Actually Pay Off?

Every senior leader is under pressure to show that AI spend translates to business value, but the path from investment to measurable outcomes is rarely linear. This panel brings together executives to share unfiltered perspectives on how they are defining, measuring, and communicating success for AI at the enterprise level, holding their organizations accountable to results, and making the tough call on when to double down, pivot, or walk away. From navigating board expectations and financial scrutiny to recalibrating strategy when pilots don't deliver, panelists will discuss what it genuinely takes to turn AI ambition into sustained competitive advantage. This is not a conversation about technology. It is about leadership, accountability, and the strategic choices that separate AI leaders from AI laggards.

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Shared the stage with

Working on now

Dessa Gypalo leads the Data, Analytics, and Automation (DnA) team at Save the Children US

About

<p><span style="color: rgb(36, 36, 36);">Dessa Gypalo has spent almost two decades working at the intersection of data, technology, and policy. Her work centers on turning data and AI investment into measurable impact. She is the Head of Data, Analytics, and Automation at Save the Children, where she leads the strategy, roadmap, and implementation of enterprise data and AI readiness.</span></p><p><span style="color: rgb(36, 36, 36);">Previously, Dessa served as Chief Data Officer for the State of Illinois and as the inaugural Chief Data Officer for Cook County. Before her work in government, she held leadership roles in advocacy organizations, a civic tech software company, and community organizing institutions, always centering the people affected by the technology, with data privacy and ethics in mind.</span></p><p><span style="color: rgb(36, 36, 36);">Dessa is active in local and national data communities, focused on developing women in data leadership, and is an alum of the Obama Foundation's Leaders USA program and the UChicago Civic Leadership Academy.</span></p><p><br></p>

Summarised from public LinkedIn activity ·

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146 leaders share three or more of Dessa's priorities

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