Chuck Siu

Visionary
DISC Type : Ds

Vice President Product Mgmt - Enterprise Journey & AI Transformation at Gap Inc.

San Francisco, California, United States

Overview

Chuck Siu is the VP of Product for Enterprise Journey & AI Transformation at Gap Inc. , leveraging his prior experience as CIO at Anaplan. He specializes in bridging the gap between AI innovation and enterprise adoption. He holds BS and MS degrees from Washington University in St. Louis and is a certified Project Management Professional (PMP).

Colleagues describe him as enthusiastic, personable, creative, and driven. He is passionate about professional development and empowerment, having recently led a workshop focused on igniting inner power and building confidence. He actively shares his hands-on experiments with AI tools, such as testing the performance of chatbots.

Unique fact: At a previous role, his IT team transformed from AI-skeptical to an AI-forward support crew in just four weeks.

Personality Overview

Big Vision Person

Risk Tolerant

Early Adopter

They are very professional in their approach and can weigh multiple perspectives together.  Reading between the lines and seeing beyond your words comes naturally to them. They might take some time to make their mind up but once they do, they don't change it easily.

Topics They Care About

Enterprise AI Adoption
Focuses on implementing AI beyond simple search, enabling deep reasoning and multi-shot workflows in large organizations.
IT Transformation
As a former CIO, he has deep experience in managing large enterprise application stacks and restructuring global IT and Agile programs.
Professional Empowerment
He speaks on topics like building confidence and igniting inner power, showing a passion for mentorship and helping others grow.

Media Appearances

Chuck has no verified media appearances

Work History

10-2025
Vice President Product Mgmt - Enterprise Journey & AI Transformation at Gap Inc.
7-2022 - 10-2025
CIO, VP IT & Enterprise AI Transformation at Anaplan
4-2022 - 7-2022
Sr Director, Platform Engineering, Security & Privacy BusOps at Anaplan
1-2021 - 4-2022
Director, Information Security Business Integration & Operati at Anaplan
9-2018 - 5-2021
Chief-of-Staff to the CISO, Global Security & Privacy Program Integrator, Mattel at Mattel, Inc.

Education

1985 - 1988
BS MS from Washington University in St. Louis
Bachelor of Arts - BA from Coe College

More Information

Social Presence :

Prographics :

Exp : 26 Location : San Francisco, California, United States Job Level : Senior Designation : Vice President Product Mgmt - Enterprise Journey & AI Transformation at Gap Inc.

Interested in

Sports

Swimming

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Insights For Selling To Chuck

During A Call Or A Meeting

DO's

  • Let them know of potential risks but suggest mitigation methods alongside
  • You can spend time on BANT (or other qualification methodology) but keep it to the point
  • Use phrases like 'your team deserves', 'best in class' etc.

DONT's

  • Don't get into pricing discussions early on, steer conversation towards proven results
  • Don't shy away from asking hard questions, but be extra polite
  • Don't take their patience for granted, avoid long-winding sermons

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Chuck is

  • Strong proof of impact and their conviction will matter the most, but they wouldn't want to act unilaterally either
  • Will you ever get a clear answer from Chuck

  • They will say no if they are not convinced but you will have to prompt them.

Insights For Deal Planning

    How fast (or slow) will Chuck move?

  • They will want to understand things well but can move fast once they have a clear picture.
  • Can Chuck take some risk or not?

  • They have good risk tolerance but are likely to think it through once or twice.

You And Chuck

Personality Compatibility


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