Seven dimensions, learned the expensive way.
Nearly thirty years in engineering leadership — CTO, VP Engineering and principal-level roles — before any of this was about diligence. Senior Director of Software Development at Twitch, founding its Seattle site engineering organisation. Then Chief Technology Officer at Woot.com, an Amazon company.
The M&A work started there, in early 2022. As CTO I worked closely with Amazon's Corporate Development team through several acquisitions and divestitures — on the operator's side of the table, the one that inherits whatever the diligence missed. That is a different education from reading a data room: you find out which questions mattered eighteen months later, when your own team is living with the answer. A year as CTO at Valdera after that, then back to Amazon for the other side of it.
In late 2024 I joined that team, as Principal, M&A Technology and Engineering Integration at Amazon — the principal technical leader for Amazon Corporate Development — leading the buy-side technical diligence on five strategic AI-capability acquisitions for AWS. Assessing the architecture and the engineering practice, judging what a team could actually deliver after close, and putting it in terms a deal team could act on.
The pattern repeated. The risks that mattered were rarely the ones in the data room. They were in how a team worked, what they knew they had deferred, and whether anyone left could safely change the system. The questions that changed a recommendation were almost never on the standard checklist — whether the code had a real history, whether the team survived one departure, whether the abstractions had been earned or imported. And they were answerable in the first afternoon, if you knew where to look.
Since 2026 I have run that work independently, through AELaboratories: buy-side diligence for private equity and growth investors, sell-side readiness for companies going into a process, and the integration planning that has to follow a yes.
Knowing where to look is the thing this tool encodes. The deterministic layer runs the checks a senior reviewer runs in the first hour. Where judgement is needed, a panel of models reads independently and disagreement is shown as disagreement rather than averaged into a score.
And if you need me on site, or remote, putting that judgement directly to work with your team — that is the engagement. Two to four weeks, adaptable to your timeline, ending in a plain-English risk register an investment committee can read, with the detailed findings and the evidence behind them. I can run it end to end, or work alongside your own engineers when you want them leading it. Buy side: what you are about to own, what it will cost to absorb, and which of your systems it lands on. Sell side: what a buyer's adviser is going to find, early enough that you can still fix it. After close: the integration plan, run by the person who wrote the assessment.
Senior Director of Software Development at Twitch, founding the Seattle site engineering org. Then CTO at Woot.com, an Amazon company. The side of the table that gets assessed.
As CTO, working with Amazon's CorpDev team through several acquisitions and divestitures. Inheriting what the diligence missed, which is how you learn which questions were the ones that mattered.
Principal technical leader for Amazon Corporate Development. Buy-side diligence on five strategic AI-capability acquisitions for AWS — and living with the calls that turned out wrong.
The same work for acquirers who are not Amazon, plus sell-side readiness and post-close integration.
That first afternoon of work, on any repository, in minutes — and free on a public one.
What used to take a week of a senior engineer's attention is now free on a public repo and €249 on a private one. An engagement starts where that finishes: the team interviews, the levelling, the incident history, and the integration plan against your stack — all of it on top of a repo survey that is already done.