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James Phillips

Strategic Director

James Phillips is the President of Financial Services at Stripe, formerly the President of the Digital Transformation Platform Group at Microsoft, a product development group spanning Microsoft’s business applications and services. With responsibility for strategic direction, development and delivering results from a broad product group that includes Dynamics 365, Power Platform, Azure AI Platform, Azure Data Platform, Azure IoT Platform, and the Microsoft Cloud for industry specific solutions, Phillips works deeply on accelerating digital transformation for businesses and enterprises – from the tech stack to customer satisfaction to team management.

As Strategic Director, James advises Madrona portfolio companies at the earliest stages of innovation and, with later stage companies, as they build to scale.

Prior to joining Microsoft, Phillips was a serial entrepreneur most recently as a founder and CEO of Akimbi Systems (acquired by VMware) and a co-founder at Couchbase (NASDAQ: BASE); held engineering, product management, corporate development and marketing leadership roles at Intel, VMware and Synopsys; and spent two years as a technology investment banker with UBS PaineWebber. He began his career as a self-taught software developer and co-founded Fifth Generation Systems (acquired by Symantec) at age 17.  He is also an angel investor and actively mentors start-up CEOs.