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AI Readiness Assessment
Where you actually are, where you think you are, and the shortest path between them.
AI strategy for software and technology companies
Your board wants an AI plan. Your engineers are already using AI tools. Nobody has decided what is safe, what is worth paying for, or what to build first. We have done this inside software companies, including PE-backed ones, and we will give you a straight answer in writing.
The three failure modes
In every case, you are paying for it: in spend you cannot explain, in tools you cannot see, or in a hire walking into a strategy that still does not exist.
Leadership read the same article you did. Tools get bought before problems get defined. Pilot projects multiply, ownership scatters, and twelve months later the only thing the company can measure is spend.
The risks are real, so nothing ships. Meanwhile, employees are vibe-coding their own mini apps with no thought to security, hosting, or maintenance, and your compliance posture is fictional.
The board wants an owner, so you open a Chief AI Officer search before anyone has scoped what the role owns. Six months and a six-figure package later, they spend quarter one writing the roadmap you could have had already.
Free · five minutes
Twenty-four yes-or-no questions on how you use AI, protect your data, run your engineering, manage vendors, and lead. Your score appears the moment you finish. No email needed.
The same ground we cover in an assessment, as a quick self-check.
What we do
It starts with a free phone call. If there is a fit, the first step is a small, fixed-price project so we both get a feel for the work. Every engagement has a defined scope and a defined deliverable. We do not bill by the hour and we do not pad timelines.
Where you actually are, where you think you are, and the shortest path between them.
A working vocabulary for your executive team. No jargon, no hype, no hand-waving.
Get your engineers productive with the tools they will actually keep using next month.
Embedded with your product and engineering teams. Ship features, not slide decks.
Start with a free call. We will tell you honestly whether you need any of this, and what a small first project would look like.
Work we have shipped
A selection from recent engagements, including PE-backed software companies. Clients described by stage and industry.
An AI image analysis pipeline for identification, built for a PE-backed B2C SaaS company.
AI enablement for two cohorts at a PE-backed B2B SaaS company, finishing with internal guidelines published.
A document processing pipeline for financial services, built for a PE-backed B2B SaaS company.
Who you will work with
Thirty years in software engineering, fifteen of them as a CTO for private equity-backed companies. Author of the Amazon bestseller Think Like a CTO and a Java Champion. Now focused on making AI work in production, not in demos.
Fifteen years in cloud and platform engineering. As VP of Engineering he took a 24/7 marketplace handling 200 million daily requests to 99.9% uptime. He brings that reliability discipline to deciding where AI belongs in your stack.
How we work
We work on AI for a living. That is exactly why we are skeptical of most of what is sold under that label. Here is how we work.
Plenty of problems need a better process, not a model. When AI is the answer, we use it to help your team ship more.
We take no referral fees from any vendor, so our advice is yours.
No retainers that quietly renew, no scope that quietly grows. You know the cost before we begin.
We will explain what you need to know. Then we will help you build it. Most firms stop at the explanation.The ThinkLikeACTO.ai team
What we are watching
Read the full edition →
· Policy
SourceCIO
In Meta commercial terms changes slated to kick in on October 30, the company will shift the liability for any mistakes made by its AI models to its enterprise customers.
Why it matters
Enterprises using Meta's AI must prepare for a significant shift in legal liability for model errors.
Our take
This is a clear example of vendor lock-in risks. Companies need to be careful about who they trust when the provider refuses to stand behind their product.
Request a free call and send a short note. A partner replies within one business day with a straight view on whether the readiness assessment makes sense for you, or whether you need something smaller.