Archive - The Pragmatic CTO

Why Most Tech Acquisitions Destroy the Thing They Paid For

Over the years I had the opportunity to be part and/or watch several acquisitions; from both sides of the table.

May 19 • Allan MacGregor 🇨🇦

When Tokens Become OKRs

Why agentic coding mandates measure consumption, not product — and what to track instead

May 12 • Allan MacGregor 🇨🇦

March 2026

AI Wrote the Code. Who Gets the Tax Credit?

Your AI Strategy Is Shrinking Your Tax Credit (Maybe)

Mar 9 • Allan MacGregor 🇨🇦

What to Measure When the CEO Asks for Engineering Metrics

How to make sure you are measuring the right things

Mar 2 • Allan MacGregor 🇨🇦

February 2026

The AI-First Fallacy

When Branding Masquerades as Strategy

Feb 23 • Allan MacGregor 🇨🇦

No Vibes Allowed: Context Engineering for Real Codebases

Context engineering as discipline

Feb 20 • Allan MacGregor 🇨🇦

The Software Factory: When No Human Writes or Reviews the Code

StrongDM's radical experiment with AI-generated code

Feb 18 • Allan MacGregor 🇨🇦

When AI Agents Write Your Code, Does Language Choice Matter?

Programming languages in the AI era

Feb 17 • Allan MacGregor 🇨🇦

OpenAI Didn't Buy a Product. They Bought a Distribution Channel.

The Token Economics Behind the OpenClaw Acqui-Hire

Feb 16 • Allan MacGregor 🇨🇦

Rise of the Citizen Coder: The Other Side of the Agentic Revolution

Part II — Death of a Craftsman

Feb 16 • Allan MacGregor 🇨🇦

Shielding the Team Doesn't Mean Silence

You didn't shield too much. You communicated too little.

Feb 14 • Allan MacGregor 🇨🇦

The OpenClaw Gold Rush

When the Wrapper Economy Outruns the Security Response

Feb 13 • Allan MacGregor 🇨🇦

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