Primary Job Title President, Microsoft North America Primary Organization
Microsoft
Location Malvern, Pennsylvania, United States Regions Greater Philadelphia Area, Great Lakes, Northeastern US Gender Female
LinkedIn View on LinkedIn X (Twitter) View on X
Deb Cupp is the President of Microsoft America, leading a $58 billion business responsible for delivering the full product and services portfolio of Microsoft to customers based in the United States and Canada. Deb is responsible for the sales strategy, execution, and revenue growth for the Microsoft US and Canada business which spans enterprise,
public sector, small and medium businesses, services, and partner communities. She leads a 10,000-person team pursuing Microsoft’s mission to empower every person and every organization on the planet to achieve more. Prior to her current role, Deb was Corporate Vice President of WW Enterprise and Commercial Industries. She was responsible for the development and execution of Microsoft’s strategy and go-to-market approach with enterprise customers across seven commercial industries: Automotive, Energy, Financial Services, Healthcare, Manufacturing, Media & Communications, and Retail & Consumer Goods. Deb led a team accountable for driving the industry point of view through both product development and customer delivery in both strategic and scale motions. During her tenure, Microsoft launched the first Industry Cloud for Healthcare in October 2020. This was followed by the announcement of additional Industry clouds in February 2021 when Microsoft shared their continued commitment to expand industry investments. Deb also serves on the Board of Directors for Avanade, the leading provider of innovative digital and cloud services, business solutions, and design-led experiences on the Microsoft ecosystem.
Pre-Microsoft Work Experience Prior to joining Microsoft in 2018, Deb spent 6 years at SAP. Most recently, Deb was the Senior Vice President (SVP) and Managing Director of Success Factors for North America. Deb was responsible for leading the HR business by driving sales and the go-to-market strategy and for overseeing operations for the field sales organization. Deb joined SAP in October of 2011 as Vice President of Sales for SAP’s healthcare business in the U.S., where she oversaw the payer and provider sales teams, which she led to double-digit, year-over-year growth. Deb was then SVP and Managing Director of SAP’s Regulated Industries practice in the U.S., which included the Federal, State, Local, Utilities, and Healthcare businesses. In that role, she guided the execution of the division’s market strategy and was responsible for business operations and revenue performance. Prior to SAP, as Vice President of Sales for Standard Register’s healthcare business, Deb helmed a national organization of sales professionals in 10 regional markets. With ultimate responsibility for the division, she worked directly with her sales teams to drive acquisition, retention, and expansion efforts in the highly competitive healthcare arena, an achievement that would cap off her 17-year tenure with the company. A collaborative and authentic leader, Deb’s focus on re-engineering and optimizing processes has enhanced productivity and driven results for the businesses under her leadership. Deb is highly focused on customer success and people development and takes a particular interest in mentoring women in business. Education Deb holds a Bachelor of Science Degree in business administration with concentrations in marketing and finance from the University of Richmond in Richmond, Virginia, where she was a Division One field hockey and lacrosse scholarship athlete. In addition, she holds an MBA from St. Joseph’s University in Philadelphia, Pennsylvania. er leadership. Deb is highly focused on customer success and people development and takes a particular interest in mentoring women in business.
Deb holds a Bachelor of Science degree in business administration with concentrations in marketing and finance from the University of Richmond in Richmond, Virginia, where she was a Division One field hockey and lacrosse scholarship athlete. In addition, she holds an MBA from St. Joseph’s University in Philadelphia, Pennsylvania.


