The Pragmatic CTO | Allan MacGregor 🇨🇦 | Substack

Your AI Pentester Found 1,000 Bugs. None of Them Were the One That Mattered.

The gap between 'faster at finding XSS' and 'can replace a human pentester' is enormous — and the industry is conflating the two.

Feb 12 • Allan MacGregor 🇨🇦

The Culture Tax

Managing internal and organizational culture

Jun 29 • Allan MacGregor 🇨🇦

Lines of Code Are Back (And It's Worse Than Before)

The metric we killed is back, and AI made it worse

Feb 8 • Allan MacGregor 🇨🇦

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 🇨🇦

Most Popular

Lines of Code Are Back (And It's Worse Than Before)

Feb 8 • Allan MacGregor 🇨🇦

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

Feb 17 • Allan MacGregor 🇨🇦

The AI Backlash Is Here

Jan 5 • Allan MacGregor 🇨🇦

Code Review Is the Bottleneck

Feb 11 • Allan MacGregor 🇨🇦

Recent posts

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 🇨🇦

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 🇨🇦

Top posts

Lines of Code Are Back (And It's Worse Than Before)

Feb 8 • Allan MacGregor 🇨🇦

Your AI Pentester Found 1,000 Bugs. None of Them Were the One That Mattered.

Feb 12 • Allan MacGregor 🇨🇦

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

Feb 17 • Allan MacGregor 🇨🇦

The AI Backlash Is Here

Jan 5 • Allan MacGregor 🇨🇦

Code Review Is the Bottleneck

Feb 11 • Allan MacGregor 🇨🇦

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