SMB AI Software · Strategic Frameworks

Playbooks

Hub-level playbooks on AI-native software, the SMB ops stack, build vs buy, and the operating discipline of running lean. Strategic frameworks for founders and operators at 20-200 person companies evaluating where the AI lever actually pays off.

SMB AI Strategy
You Don't Need the Expert. You Need the Expert's Workflow.

A field report: a non-engineer deployed servers, fixed a payment bug, and wired analytics in one evening with AI. The honest framework for when a generalist plus structured AI can do specialist work — three conditions — and the line where you still need the human. Bias on the table, written by someone who builds exactly this.

Tom Christian June 25, 2026 ~8 min read
SMB Operations
The One-Person Back Office: Running Support, HR, Training, and Knowledge Without a Department of Any of Them

Between employee five and fifty, you acquire four departments and hire none of them. They all run the same loop — intake, triage, respond, document, improve — and it breaks at the same step every time. The operating pattern, the stack principles, and where each function's deep-dive lives.

Tom Christian June 24, 2026 ~11 min read
Software Strategy
Build vs. Buy: When a Lean Team Should Build Its Own Software (and When It Shouldn't)

The default answer is buy — and "we could build that ourselves" is not a reason to override it. The maintenance iceberg that sinks most build decisions, the four questions that actually settle it, and why AI changed this math less than the hype claims. From a solo founder who built four products and still tells you to buy.

Tom Christian June 5, 2026 ~14 min read
Buyer's Framework
AI-Native vs. AI-Feature: How to Tell the Difference Before You Buy

Every SaaS company added "AI-powered" to their landing page in the last 18 months. Most of them are lying. The five-question framework that exposes whether the AI is structural or decorative — in five minutes of a demo, before you commit a quarter of budget.

Tom Christian June 3, 2026 ~16 min read
More playbooks publishing weekly.