Jeff James: three decades, four chapters.
Over two and a half decades at Microsoft, most of it making enterprise operations run at scale. Now building agent fleets in the open and helping teams become AI native, bringing decades of hard-won experience to teams that are moving too fast to learn it the slow way.
Engineering GM at Microsoft. Core team member that built Office 365.
Led the agentification of FastTrack operations.
Independent: writing, building, and advising on AI transitions.
The four chapters
From the support queue to product management
Support technician through program management, systems engineering, and product management, in the PC-to-mainframe world. I learned to drive engineering change from direct customer experience, and I've never stopped. (First consulting gig at age 11: a Lotus 1-2-3 worksheet for my dad's marketing firm.)
The startup years
Every hat there was: support, IT, business development, product design, while the company grew from six people to fifty, then shrank back to fifteen. The best education in pace, scrappiness, and what actually matters that money can't buy.
Enterprise operations at scale
Engineering GM and core team member that built Office 365: solution architect with the first managed-service customers to sales executive closing the first productivity-cloud deals in Japan and US life sciences. Built FastTrack Architects from concept to a global organization, including a customer-health metric that sits on an EVP scorecard. Most recently GM of New Commerce FastTrack: the modern-commerce transition for roughly 40,000 enterprise customers.
The last act: turning FastTrack operations from manual knowledge work into an agentified operating model. The path we took became E3 (Evangelize, Enable, Empower), and the results are below.
Building in the open
I run a fleet of named agents that capture, file, and surface everything I think out loud, build approved features while I sleep, and report their own costs. I write about all of it at signalnotsentiment.com. The tools change weekly; the judgment is the durable part.
What the last act measured
Measured from day one: every agent treated as an operational investment with telemetry. Evidence beat anecdotes, every time. The full story is in the E3 overview.