Andrew Osten

Trailblazer
DISC Type : DI

General Manager, Global Digital Transformation, Microsoft Digital at Microsoft

Toronto, Ontario, Canada

Overview

Andrew Osten is a global digital transformation executive at Microsoft, leading a large international team to drive business and AI transformation. With an MBA from Wilfrid Laurier University, his expertise lies in technology strategy, change management, and operations for large-scale enterprise organizations.

Outside of his corporate role, Andrew draws inspiration from his family, having shared thoughts on empowerment in leadership after encouragement from his daughter. His interests also extend to the technology and entertainment space, including companies like Electronic Arts.

He leads a global organization of over 100 team members located across 16 different countries.

Personality Overview

Achievement-Oriented

Friendly But Fast

Values Relationships

They do not mind taking risks and can make hard decisions, if necessary.  They respond better to a combination of speed and relationship. They will bat for you if they come to believe in you.

Topics They Care About

Enterprise Change Management
He is a PROSCI certified leader who emphasizes that a dedicated focus on change management is critical for driving technology adoption and achieving ROI from IT investments.
AI Transformation
His current role focuses on leading a global AI transformation and he is involved in Microsoft's strategy of embracing AI to revolutionize IT services and operations.
Global Leadership
Leads a global shared services organization within Microsoft Digital, with more than 100 team members located across 16 countries.

Media Appearances

Reflecting on 50 years of IT at Microsoft: Five key lessons and insights on the future. Featured in Microsoft Inside Track Blog

See Now

Work History

9-2004
General Manager, Global Digital Transformation, Microsoft Digital at Microsoft
2001 - 2004
Manager Consulting Services at Capgemini
1999 - 2001
Management Consultant at Ernst & Young
1995 - 1998
Marketing Channel and New Business Consulting at Various

Education

1998 - 1999
MBA from Wilfrid Laurier University
1993 - 1998
Bachelor of Commerce - BCom from York University

More Information

Social Presence :

Prographics :

Exp : 31 Location : Toronto, Ontario, Canada Job Level : Senior Designation : General Manager, Global Digital Transformation, Microsoft Digital at Microsoft
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Insights For Selling To Andrew

During A Call Or A Meeting

DO's

  • Showcase existing customers and use case-studies to grab their attention
  • Talk about yourself and some of your achievements at the start of the conversation
  • Build a trustworthy relationship while keeping the product center-stage

DONT's

  • Don’t hesitate from asking them how they truly feel about your product
  • Don't make any commitments that you might not be able to fulfill
  • Don’t force involvement of other stakeholders unless it is critical

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Andrew is

  • Relationship and product conviction matter equally, followed by a sense of achievement.
  • Will you ever get a clear answer from Andrew

  • If they are not convinced, they will say no albeit in a friendly manner.


Insights For Deal Planning

    How fast (or slow) will Andrew move?

  • They can make decisions quickly if they develop trust in you and conviction in the product.
  • Can Andrew take some risk or not?

  • They can take risks if necessary.

You And Andrew

Personality Compatibility


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