Three chapters. One operator.

Twenty-six years at Microsoft, a $1M+ ARR business built and wound down solo, and real AI systems shipping today. Three different chapters, each building a distinct capability. Together they add up to an operator who speaks both engineer and C-suite, and can navigate the stack top to bottom.

Align to the mission, define the plan, break it down, prioritize, execute, inspect, adapt, communicate.

Chapter 01 / 1994–2020

Microsoft scale

26 years across Xbox, HoloLens, and Windows Hello. That span built technical depth and the delivery leadership to ship complex things across many teams.

Chapter 02 / 2021–2026

Owning the business

Built and ran a $1M+ ARR service business solo, owning the full P&L, strategy, and real stakes. The job forced a shift from tracking output to proving outcomes.

Chapter 03 / 2025–present

Hands-on with AI

A deliberate return to building, shipping real AI systems and wiring AI into how an organization actually operates.

Selected work

What actually shipped.

A tight set of case studies, tagged by the competency each one demonstrates. Every piece leads with outcomes, and the technical ones go deeper on architecture underneath.

Filter by competency

Technical systems at scale

The metric said 99%. The customers said otherwise.

Windows Hello reported 99% success while users were failing to log in. I invented the metric that told the truth, then used it to drive real success from ~65% to over 90%.

Program & Systems ExecutionInfluence Without AuthorityData-Driven Judgment

Integrity under personal cost

The org didn't need my role anymore. I was the one who said so.

Tasked with building headcount-reduction scenarios for my own org, an honest read of what the new direction actually needed pointed at one function: mine. I recommended cutting it, then let a canceled backup plan and a false-start job search show me what I actually wanted next.

Integrity-Driven Decision-MakingData-Driven Judgment

Quality engineered into every step

The metric said growth. The leak was retention.

Growth metrics hid a $150K revenue leak until a gross-retention number told the truth. The fix was a new accountability role, filled by moving an operations manager into the growth seat he'd already earned, without adding headcount. Retention 65%→85%, quality 80%→95%, cash-flow-neutral.

Data-Driven JudgmentProgram & Systems ExecutionCrisis & People Leadership

Leverage without a title

Ninety days decide a new CEO's priorities. I made sure ours landed first.

When a struggling franchise system got a new CEO after three years of stagnation, I had no formal authority over him, just a board seat and forty percent of the system behind me. I used it before he asked, and the working relationship we built outlasted my own exit from the business.

Influence Without Authority

Leadership under real stakes

Winding down a business without breaking your word

A business that had quietly stopped fitting its market forced the hardest call I've ever made. Keep digging or shut it down. A four-priority framework decided it in advance; an orderly wind-down honored every obligation it could.

Crisis & People LeadershipIntegrity-Driven Decision-MakingData-Driven Judgment

AI-native planning & judgment

Cadence tells you when to look. Alignment tells you if it matters.

This is how I think about the planning and rhythm-of-business problem, built AI-native: an agent runs the review cadence, I keep the judgment call. It caught a week that looked like 90% mission-aligned success, when 85% of that was actually defensive work.

AI Systems BuildingProgram & Systems ExecutionData-Driven Judgment

AI-native pipeline engineering

Sourcing to submission, so my time goes to judgment.

An AI-driven job application pipeline: discovery, fit screening, resume and cover letter generation, tracking, engineered so my time goes to judgment. The bank matches and aligns my own verified experience to a job, always drawn from what I actually did.

AI Systems BuildingProgram & Systems Execution

How I work

The AI-native operating stack

Built on agents and PRD-first discipline, with Claude Code as the build partner behind every case study on this site.

How I work

Writing

The thinking, written down

An excerpt from a published memoir on the ownership years, plus selected essays on building real AI systems.

Read the writing

About

The full arc

How three careers' worth of capability ended up in one operator, and here's what that means for the team that hires me.

About Will

Let's talk.

If the fit is real, I want the conversation.

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