Jay Cook
Leadership story · One direction, different customer contexts

Outlook for Web

Led Outlook on the web for a decade, including the convergence of Outlook.com and Outlook Web App.

Convergence began with customer needs, priorities, and product architecture—not with making every interface the same.

One web platform, multiple customer contexts

I worked on Outlook on the web from March 2010 through May 2020 and led the UX team from approximately July 2014 onward. During the later years, I simultaneously led Windows Mail and Calendar. Outlook.com and Outlook Web App served different audiences, product histories, and expectations. The work was not simply to merge interfaces, but to create one experience direction without erasing meaningful customer needs and differences.

Platform convergence

Build a shared foundation

Over 18 months, I led the experience strategy with Engineering, Product Management, and Research: evaluate the strengths of both products, simplify inherited complexity, and define a coherent model for consumer and commercial customers. Progressive onboarding helped move nearly one billion legitimate mailboxes while excluding those likely tied to malicious accounts and protecting familiar workflows.

Experience transformation

Make change reversible

Modernizing the front end created room to reset both the product and how the organization worked. I established a customer-centered vision, mapped more than 150 opportunities, and used a vision prototype to align Design, Research, Product Management, and Engineering. An opt-in path let customers try the new experience without losing the familiar one, reducing adoption risk as we learned and iterated.

Scale became a platform for what came next

The unified foundation gave Outlook one web surface for continued product development and experimentation. Consumer and commercial teams could evolve from a shared base without treating their customers as identical.

Building what’s next—and looking for a design leader to help make it real?