Alyssa Cox

VP Enterprise Transformation at Cardinal Health

Member since November 2023

Education: Duke University - Temple University, University College Dublin
Chicago, IL, USA

Biography

Alyssa Cox is not a futurist or a theorist—she is a battle-tested corporate executive currently in the trenches of enterprise transformation. As the Vice President of the Transformation Management Office for a Fortune 15 healthcare leader, Alyssa has successfully managed multi-million-dollar AI and digital process transformations across global teams.

She specializes in helping organizations move beyond "AI tourism" to build practical, scalable operating models that drive measurable ROI, while successfully leading workforces through complex technological disruption. When Alyssa speaks, audiences do not just get inspiration; they get the blueprints, governance frameworks, and change-management strategies used in today’s most successful enterprise boardrooms.

Example Talks

The Translator-in-Chief: Bridging Tech Capabilities and Business Reality

​The Challenge: Technical teams build things the business doesn't need, and the business demands things technology cannot safely deliver.

The Keynote: Traditional command-and-control leadership fails in digital transformations. Alyssa teaches leaders how to become "Techno-Functional Translators" who successfully align complex IT capabilities with strict commercial goals.


Audience Takeaways:


  • How to facilitate highly effective governance between IT and business units

  • The anatomy of a successful Transformation Management Office (TMO)

  • Leadership strategies for navigating ambiguity and driving cross-departmental alignment

​

From Skeptic to Practitioner: Managing the Human Side of AI Disruption

​The Challenge: AI adoption is often treated as an IT project when it is actually a massive human change-management challenge. Unaddressed workforce anxiety kills transformation ROI.

The Keynote: Drawing from her experience leading massive cross-functional teams, Alyssa shares how to redesign workflows and guide employees through the psychological impacts of automation.


Audience Takeaways:


  • The "Human + AI" blueprint for successfully augmenting (rather than alienating) your workforce

  • Tactical communication strategies to turn internal AI skeptics into super-users

  • Frameworks for mapping new reskilling pathways for operational teams

​

The $M Playbook: Scaling Enterprise AI from Pilot to Production

​The Challenge: Most organizations are stuck in "pilot purgatory," experimenting with AI but failing to operationalize it at scale to achieve real financial returns.

The Keynote: Alyssa pulls back the curtain on what it actually takes to scale automation and AI across a massive enterprise. She provides a pragmatic look at prioritizing high-ROI use cases, securing executive alignment, and building resilient operating models.


Audience Takeaways:


  • The 90-day execution framework to transition from sandbox experiment to production

  • How to identify and avoid the hidden operational costs of scaling AI

  • Metrics that matter: Moving from "vanity metrics" to true business ROI

​

Topics/Keywords

digital and ai transformation womens leadership transformational leadership leadership managing change scaling

Speaking Engagements

Windy City Summit 2025

Chicago, IL, USA, 05/13/25

2025 Buckeye Financial Forum

Dublin, OH, USA, 04/29/25

2025 HR Virginia Annual Conference

Virginia Beach, VA, USA, 04/13/25

2024 NYS SHRM Conference

Albany, NY, USA, 09/08/24

ICT Solutions and Education Expo 2024

Dallas, Texas, USA, 08/20/24

Example Talks

The Translator-in-Chief: Bridging Tech Capabilities and Business Reality

​The Challenge: Technical teams build things the business doesn't need, and the business demands things technology cannot safely deliver.

The Keynote: Traditional command-and-control leadership fails in digital transformations. Alyssa teaches leaders how to become "Techno-Functional Translators" who successfully align complex IT capabilities with strict commercial goals.


Audience Takeaways:


  • How to facilitate highly effective governance between IT and business units

  • The anatomy of a successful Transformation Management Office (TMO)

  • Leadership strategies for navigating ambiguity and driving cross-departmental alignment

​

From Skeptic to Practitioner: Managing the Human Side of AI Disruption

​The Challenge: AI adoption is often treated as an IT project when it is actually a massive human change-management challenge. Unaddressed workforce anxiety kills transformation ROI.

The Keynote: Drawing from her experience leading massive cross-functional teams, Alyssa shares how to redesign workflows and guide employees through the psychological impacts of automation.


Audience Takeaways:


  • The "Human + AI" blueprint for successfully augmenting (rather than alienating) your workforce

  • Tactical communication strategies to turn internal AI skeptics into super-users

  • Frameworks for mapping new reskilling pathways for operational teams

​

The $M Playbook: Scaling Enterprise AI from Pilot to Production

​The Challenge: Most organizations are stuck in "pilot purgatory," experimenting with AI but failing to operationalize it at scale to achieve real financial returns.

The Keynote: Alyssa pulls back the curtain on what it actually takes to scale automation and AI across a massive enterprise. She provides a pragmatic look at prioritizing high-ROI use cases, securing executive alignment, and building resilient operating models.


Audience Takeaways:


  • The 90-day execution framework to transition from sandbox experiment to production

  • How to identify and avoid the hidden operational costs of scaling AI

  • Metrics that matter: Moving from "vanity metrics" to true business ROI

​

Speaking Engagements

Windy City Summit 2025

Chicago, IL, USA, 05/13/25

2025 Buckeye Financial Forum

Dublin, OH, USA, 04/29/25

2025 HR Virginia Annual Conference

Virginia Beach, VA, USA, 04/13/25

2024 NYS SHRM Conference

Albany, NY, USA, 09/08/24

ICT Solutions and Education Expo 2024

Dallas, Texas, USA, 08/20/24

Topics/Keywords

digital and ai transformation womens leadership transformational leadership leadership managing change scaling