Fractional CTO · CIO · COO / Operating advisor
Hope is not an operating model.
A CEO asked the program lead on the company's biggest goal whether they would hit the next milestone. The answer was “I hope so.”
That is the moment I get brought in.
Previously Amazon / Microsoft
Can your team answer these today?
Five questions I ask on day one. Most delivery organizations can't answer them.
- 01
How work gets in
Why are we funding this, and how did it earn its place on the roadmap? If anything can get in, nothing is a priority.
- 02
Your waterline
Money moves. Priorities move. Against your real capacity, what is above the line, what gets pushed, and what does it cost?
- 03
How decisions get made
Who decides, on what inputs, and how fast. Your PM can walk you through the critical path. You need a way to decide now.
- 04
Your data
What the numbers say, not what the status report says.
- 05
Your assumptions
Documented, then burned down as fast as possible. Every open assumption is a risk you haven’t priced yet.
When those answers are clear, you don't need five project managers to answer a simple question. When they aren't, adding more won't help.
I drop in, find where the work actually breaks, and install mechanisms.
I trace how work moves from idea to production and replace status meetings and heroics with clear owners, clear inputs, and a weekly cadence that tells leadership what is actually true.
At Amazon that meant replacing more than 70 redundant dashboards with a single source of truth for 20+ engineering teams across 66 countries. The same approach works in a 40-person portfolio company.
Proof it works at scale.
- $1.4B
Technology organization governed. The operating model I built ran it.
- $100M
Annual automation savings delivered. Against a $1.4B Opex base.
- $268M
The largest Healthcare Enterprise Agreement in Microsoft history. A record that still stands.
- 12B+
Annual transactions. One platform. The infrastructure behind every corporate hire Amazon made globally.
- 5,000%
Platform growth scaled in under 60 days. The platform was on fire when I arrived.
I take on a limited number of fractional CTO and advisory engagements. PE firms evaluating portfolio companies are a particular focus.
Current engagement: Fractional CTO for a PE-backed healthcare technology company. If you are a PE firm evaluating a portfolio company, a founder scaling beyond early-stage execution, or an enterprise in transformation, we should talk.
The frameworks I build professionally and personally come from the same instinct.
I also write and build frameworks under the name Ross Charles, exploring what high pressure does to the people inside demanding systems and why the gap between understanding yourself and actually changing is not a willpower problem.
The Identity Pattern Framework and the yourpatternmap.com assessment came out of that work. Leaders who encounter it describe it as the most clarifying thing they have found.
If that sounds relevant to the work you do, it probably is.