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.

Operations
The 90-Minute Month-End: A Founder’s Close Without an Accountant

Your bank balance is a lagging indicator in a current indicator's costume. The five-step close a founder can run in 90 minutes: the statement read, the receivables sweep, the subscription delta, the three numbers that predict trouble, and the one-page note that compounds.

Tom Christian August 21, 2026 ~7 min read
Operations
The Payment-Change Email: The Verification Routine That Stops Invoice Fraud

The invoice is real, the logo is right, and only the bank account is a lie. Why spotting fakes is the wrong plan, the thirty-second callback rule that beats even the perfect email, and the two supports that make it survive a busy office.

Tom Christian August 11, 2026 ~8 min read
Operations
The First Ops Hire You Might Not Need

An ops hire runs $60–80k a year plus the management overhead nobody budgets. Before you write the JD, sort the work that’s drowning you: judgment earns the hire, repetition earns a system — and doing that sort in the right order often changes the answer.

Tom Christian August 6, 2026 ~8 min read
Operations
The Subscription Sprawl Audit: What You're Paying For, Using, and Quietly Duplicating

Sprawl accretes one $29 Tuesday fix at a time — every tool had a buyer, but the portfolio has no owner. The one-hour audit: name a human for every charge, map the overlapping jobs, cancel the zombies, and put every renewal on one calendar so it stops regrowing.

Tom Christian July 29, 2026 ~8 min read
Operations
The Admin-Time Audit: Find the Hours Your Team Loses Every Week

Admin time never arrives as blocks — it arrives as crumbs, too small to count and big enough to eat a working day per week. The one-week tally method that makes it visible, and the four-bucket call (automate, design out, delegate, keep) that follows.

Tom Christian July 23, 2026 ~8 min read
SMB Operations
The 90-Day Plan to Systematize Your Back Office (Without Hiring Anyone)

You already know the back office is chaos — HR, support, training, knowledge all improvised. "Fix it" never happens because you're treating it as one big project. It isn't. Pick the one function that's bleeding the most time, systematize it, write down what you learn, roll to the next. Ninety days, one function at a time, no new hires.

Tom Christian July 8, 2026 ~9 min read
Software Strategy
The Integration Tax: Why Five Point Tools Cost More Than One Back Office

Add up your subscriptions and you'll get the wrong number. The real bill is the integration tax — per-tool admin, duplicate data entry, context-switching, onboarding overhead — that no invoice shows and that quietly becomes the owner's second job. How to total it in an afternoon, and when consolidation actually beats best-of-breed.

Tom Christian July 8, 2026 ~9 min read
SMB Operations
One Login, Four Specialists: Run HR, Training, Support, and Knowledge Without Four Hires

Between five and twenty employees, a small company acquires the org chart of a big one without the people to fill it. You need four specialist functions and can't afford four hires. The way out isn't a generalist — it's seeing that each function is mostly repeatable machinery with a thin layer of human judgment on top, and carrying the machinery for you.

Tom Christian July 8, 2026 ~9 min read
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.