Deb Cupp in

Deb Cupp

Inspirer · DISC type id
President & Chief Revenue Officer, Global enterprise sales at Microsoft
📍 Greater Philadelphia, United States

Deb Cupp is the President and Chief Revenue Officer for global enterprise sales at Microsoft, where she leads the delivery of Microsofts portfolio to enterprise customers. A graduate of the University of Richmond, she is focused on helping clients navigate their AI transformation and solve their most complex challenges.

Outside of her executive role, she is a former Division I field hockey player. This experience instilled in her a deep appreciation for teamwork and resilience, principles she applies to her professional life. She is passionate about leadership that is rooted in humility and empathy.

Unique fact: Deb is a recipient of the Spider Athletics Alumni Achievement Award from the University of Richmond for her professional distinction.

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Experience
12 Years
Current Role
President & Chief Revenue Officer, Global enterprise sales
Job Level
Leadership
Location
Greater Philadelphia, United States
Personality Overview

How Deb shows up

Decisive
Generous
Achievment Oriented

They don’t mind taking a stand if they believe in something. They respond well to objective pitches but also attach some value to relationships. They measure a product on its merit but can be influenced by strong testimonials.

Priorities

Topics Deb cares about

Enterprise AI Adoption
She consistently focuses on guiding large organizations through their AI transformations, helping them to fundamentally reimagine their operations and business models.
People-Led Transformation
Believes that the success of AI hinges on people, emphasizing that teams must feel informed and supported for technological momentum to be sustained.
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Career

Work history

10-2025
President & Chief Revenue Officer, Global enterprise sales
Microsoft
7-2023 - 10-2025
President, Microsoft Americas
Microsoft
4-2022 - 7-2023
President, Microsoft North America
Microsoft
8-2022
Board Member
Ralph Lauren
5-2019 - 6-2025
Board Member
Avanade
In the press

Media appearances

Deb Cupp – President, Microsoft US | Avanade Board Member. Featured in Apple Podcasts
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Scaling Teams with Empathy and Purpose | Deb Cupp from Microsoft. Featured in YouTube
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Education
2002 - 2003
MBA
Saint Joseph's University - Erivan K. Haub School of Business
1989 - 1993
Bachelor of Science (BS) in Business Administration
University of Richmond - Robins School of Business
Social presence
in
Behavioral profile

DISC profile (public)

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Influence (I)

Influence (I) reflects the degree to which a person prefers to work by influencing or persuading others. Those scoring high tend to be people oriented, motivated by social recognition and building relationships.

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