Deb Cupp

Deb Cupp

Executive Vice President and Chief Revenue Officer, Microsoft global enterprise | Ralph Lauren Board Member

Microsoft•Greater Philadelphia, United States

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Experience22+ Years

Executive Overview

I lead the global enterprise sales business responsible for delivering the full product and services portfolio of Microsoft to enterprise customers around the world. I am passionate about working with my team to deepen our collaborations with customers and partners across commercial and public sector industries to help them on their AI transformation journeys. As a customer-obsessed, technology executive, my vision is to accomplish things people say can’t be done. I gravitate towards difficult challenges and am at my best when working deeply with customers to solve their most vexing problems. I excel at advancing sales relationships through collaborative work and informed decision-making, and as a learner by nature, I push myself to not just listen, but to understand our customers’ needs, sift through complexity, and guide them to success. I have tremendous respect for those who can sell new business consistently and creatively. But of course, I couldn’t do all this without amazing teams. When I say I’m “team crazy,” I mean that I’m at my best when working with my teams to achieve great things. My mission is to build teams that are poised to orchestrate and execute transformative strategies for our customers. I am deeply committed to employee mentorship and development and strive to make a lasting contribution to people’s careers and lives. I have a knack for coaching and actively work to foster a culture of continuous learning. The capacity to lead comes naturally for me. One of my key strengths is the ability to inspire and mobilize people to relentlessly pursue innovative solutions. I absolutely love my work and delight in running businesses that truly need my help.

Career Timeline

Professional employment history
  • Aug 2022–Present· 4 yrs 2 mos
    • Board MemberCurrent
      Aug 2022–Present
  • MicrosoftCurrent
    2018–Present· 8 yrs 9 mos
    • EVP & Chief Revenue Officer, Global enterprise sales Current
      Oct 2025–Present
    • President, Microsoft Americas
      Jul 2023–Oct 2025
    • President, Microsoft North America
      Apr 2022–Jul 2023
    • President, Microsoft US
      Jul 2021–Apr 2022
    • Corporate Vice President, Enterprise and Commercial Industries
      Jul 2018–Jul 2021
    • Corporate Vice President, Strategy and Programs
      2018–Jul 2018
  • May 2019–Jun 2025· 6 yrs 1 mo
    • Board Member
      May 2019–Jun 2025
  • Oct 2014–Jul 2017· 2 yrs 9 mos
    • Managing Director and SVP, SAP SuccessFactors North America
      Oct 2014–Jul 2017
  • Oct 2011–Oct 2014· 3 yrs
    • Managing Director and SVP, Regulated Industries
      May 2014–Oct 2014
    • Vice President, Healthcare Sales
      Oct 2011–May 2014
  • 2009–Oct 2011· 2 yrs 9 mos
    • Vice President, Healthcare Sales
      2009–Oct 2011
  • 2004–2008· 4 yrs
    • VP, Northeast Sales
      2005–2008
    • Director, Business Development
      2004–Apr 2005

Education

MBA

Saint Joseph's University - Erivan K. Haub School of Business

Bachelor of Science (BS) in Business Administration

Marketing and Finance

University of Richmond - Robins School of Business

Executive Relationship Map

Reports To
Deb Cupp
Vice Chair & President
Chief Financial Officer
Chief Technology Officer
Chief Operating Officer

Executive Network Preview

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Skills & Expertise

20 of 20 skills
Cold CallingDirect SalesCRMLeadershipManagementNew Business DevelopmentDirect MarketingSalesSolution SellingHealthcareKey Account ManagementCoachingStrategyCross-functional Team LeadershipBusiness StrategyAccount ManagementLead GenerationSalesforce.comBusiness DevelopmentSales Operations