I shipped Xbox, HoloLens, and Windows Hello. Then I ran a service business past $1M ARR with ten people on payroll, and closed it myself when it stopped fitting its market. Since 2025 I've been building AI systems hands-on, and teaching them every other week to a room of business owners.
7 case studies below, with the numbers I actually got. A login feature whose dashboard reported a 1% failure rate while a third of its users couldn't reliably get in. A growth chart that hid a retention leak I hadn't measured in three years. A governance ladder my agents have not climbed a single rung of, because they haven't earned it yet. I built the measurement in all three, and all three came back saying something I didn't want to hear.
What I want next is the role that uses all three at once. Enough depth to be useful in a room of engineers, enough breadth to read a P&L and know which function the problem is actually in, and enough hands-on AI to do both without a team behind me. I'm in the Seattle area and open to relocation.
26 years across Xbox, HoloLens, and Windows Hello. A data team grown from 2 to 30, and delivery across orgs that did not report to me. That span built the technical depth and the cross-team leadership.
I bought a service business and ran it past $1M ARR with ten employees at peak. No partner and no safety net. P&L, sales, ops, quality, hiring, payroll, every call mine. That is where the breadth came from, and where tracking output stopped being enough.
Back to hands-on, deliberately. Real AI systems reading two live mailboxes and writing into the system I plan my week from, with the governance model written down before the code. The shape of senior work changed while I was away. This is the version the change actually calls for.
Selected work
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.
Integrity under personal cost 50-person org · 2020
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.
Leadership through an org dissolution 30-person org · 2018
A product pivot deprioritized the work my thirty-person org existed to do, and the org was dissolved rather than restructured. I had about a month, no landing plan handed down, and no seat waiting for me on the other side. Every team landed.
Technical systems at scale 3 orgs, none reporting to me · 2016-2017
Windows Hello reported 99% success while users were failing to log in. I built the metric that told the truth. The dev teams did the fixing, and real success went from ~65% to over 90%.
Leverage without a title Owner of 1 location; franchisee association president · 2025
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.
Quality engineered into every step 10 employees · 2024
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.
Leadership under real stakes 10 employees · 2025-2026
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.
Governing an autonomous system 1 operator · 2026
An agent fleet that reads my real mail and writes into the system I plan my week from. The question that mattered was never whether it worked, it was what it gets to do without me. I built the graduation ladder first, then found the gate I thought we were failing had never been computed at all.
The search is still open. I'd rather have one real conversation than ten polite ones.
w_sadler+portfolio@outlook.com Connect on LinkedIn →