About Jay
I've been in the room for 30 years. Now I lead teams through AI.
The hard part of AI isn’t the technology — it’s getting your people to actually use it. I’m the fractional Chief AI Officer who leads that change and builds the systems that make it real.
30 years in tech · Microsoft since 1996 · co-founded & exited an AI company (2024) · built the original M365 Copilot demos.
The Story
I joined Microsoft in New Zealand in 1996 as a systems engineer. That was the start — and I never really left the front edge of what technology could do for a business.
I rose through platform marketing, building "smart home" demos and press moments before the term existed. Then Microsoft HQ in Redmond, where I spent more than a decade across AI, IoT, and machine learning — turning research into things customers could actually see and use.
I co-founded Aware Group in 2016 — one of the first AI companies in the Southern Hemisphere, back when most people still thought AI was science fiction. We built it, grew it, and exited to HSO in 2024.
Along the way I built the original Microsoft 365 Copilot demos and helped bring it to market — a front-row seat on how enterprise AI actually lands inside a company.
The throughline is the same every time: take emerging tech and turn it into business value before the market catches up — and bring people with me. Because the hard part of AI was never the technology.
Today I do that as a fractional Chief AI Officer: leading teams through AI adoption and building the systems that make it stick.
The Timeline
Thirty years, ahead of the curve.
From Microsoft NZ in 1996 to fractional Chief AI Officer today — turning emerging tech into business value before the market catches up.
- 1996· Microsoft NZ
Joined Microsoft
Systems engineer — the start of a 30-year run turning new tech into business value.
- 2000s· Microsoft
Platform Marketing & "smart" demos
Building "smart home" demos and press moments two decades before it was mainstream.
- 2010s· Microsoft HQ, Redmond
AI, IoT & ML initiatives
A decade across emerging-tech experiences — FarmBeats, AI for Earth, IoT roadshows.
- 2016· Aware Group
Co-founded Aware Group
One of the first AI companies in the Southern Hemisphere — before most thought AI was real.
- 2023· Microsoft
Built the M365 Copilot demos
Built the demos that showed the market what Copilot meant for business.
- 2024· Aware Group → HSO
Exit to HSO
Aware Group acquired by HSO.
- Now
Fractional Chief AI Officer
Leading teams through AI adoption and building the systems that make it stick.
At a Glance
30+
Years in Tech
1996
At Microsoft Since
Bellevue, WA
Based In
Fractional CAIO
Role
Embedded · ongoing
Engagement Model
Aware Group → HSO, 2024
AI Company Exit
See where your team stands.
How mid-market teams actually adopt AI — and get a working AI operating model in 90 days — without a 7-figure AI hire.
