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Freedom Dumlao — Chief Technology Officer and Chief AI Officer · Vestmark · Boston, Massachusetts, United States.
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Profile updated Nov 2026 · Sourced from public professional profiles · Legitimate-interest B2B basis
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About
I've spent my career at the frontier of what AI can do in production. Voice AI at Amazon Alexa. Conversational AI at Drift. And now agentic systems at Vestmark, where we manage technology for $2 trillion in assets across broker-dealers and RIAs.
Each wave looked speculative until it didn't. That's where I tend to live.
Aside from the AI chapters, I was building platform infrastructure at scale: IoT at Xively, mobility tech at Zipcar, commerce at Wayfair. The through line across all of it is the moment when a new kind of infrastructure becomes possible and nobody has figured out the right abstraction yet.
As CTO and CAIO at Vestmark, I'm working on that problem again. My current focus is what it means to run an enterprise AI strategy at institutional scale: not just adopting tools, but redesigning how software gets built, how portfolios get operated, and how decisions get made.
I write about agentic systems, AI strategy, and the infrastructure layer nobody talks about yet at apiguy.com.