Articles
Practical thinking for the people who actually have to decide.
On fractional CTO work, AI integration, engineering leadership, and the technology decisions that shape growth-stage companies. Written for the founders, CEOs, and operators who make them.
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Strategy
What a Fractional CTO Does in the First 30 Days
A fractional CTO engagement that delivers value starts before the first big decision. Here's the playbook for the first month — what gets diagnosed, who gets met, and what changes by day 30.
Read articleAI
Where AI Actually Fits in Your Product (and Where It Doesn't)
Most "AI features" don't earn their cost. Some are genuine product unlocks. Telling the difference is mostly about being honest about what AI is good at — and what it isn't.
Read articleStrategy
How to Build a Tech Roadmap That Actually Gets Followed
Most tech roadmaps die in week three. They're either too detailed to survive contact with reality, too vague to drive decisions, or owned by no one. Here's what makes one stick.
Read articleLeadership
Five Signs You've Outgrown Your Founding Engineer
The person who wrote your first prototype is rarely the person who can scale your engineering org. Here's how to recognize the inflection point — and what to do about it.
Read articleLeadership
When to Rewrite vs. Refactor: A Decision Framework
Engineers love to rewrite. Most rewrites fail. The question of when to rewrite vs. when to refactor isn't about cleanliness — it's about the trajectory of the system and the team that maintains it.
Read articleArchive
From the library, still useful.
Why Your Engineering Team Is Shipping Slowly (And It's Not What You Think)
Velocity problems usually look like a code problem. They almost never are. Here's where the slowdown actually lives in growth-stage engineering teams — and why hiring more developers usually makes it worse.
Fractional CTO vs. Tech Advisor vs. CTO-as-a-Service
Three roles get pitched to growth-stage CEOs as roughly equivalent solutions for "we need senior technical help." They aren't. Here's what's actually different — and which one fits your situation.
Build vs. Buy AI: When OpenAI's API Beats Self-Hosting
Build-versus-buy is the most-debated AI decision at growth-stage companies, and the wrong answer can cost a year. Here's the actual framework — and why "buy" wins more often than engineering teams want to admit.
RAG, Fine-Tuning, Prompting: A Non-Engineer's Decision Tree
Three approaches dominate AI-product engineering: prompting, RAG, and fine-tuning. Vendors will tell you their pet approach is the right one. Here's the decision in plain English.
How to Evaluate an AI Integration Vendor (Without Being an AI Engineer)
AI integration vendors all sound credible in the first call. Five questions, asked early, separate the ones who deliver from the ones who burn six months of your time and budget.
The Tech Debt Conversation: Making It a Board-Level Priority
Tech debt is treated as an engineering concern. It's actually a strategic risk that compounds quietly until something breaks. Here's how to translate it for the board — and why doing so is your job, not your CTO's.
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