AI Tools for Small Business Operations
Updated: 23 hours ago
This is a post about AI tools for small business operations — specifically, four of them I've built myself this year. Sherpa Supply Chain Advisory exists to help shippers and logistics providers buy freight smarter, design better networks, and run tighter operations. But if you've talked to me in the last year, you've probably also heard me mention an estimator, a build sheet, a pricing tool, or a rental tracker I built too.
That's not a side hobby. It's the same skill set, pointed at a different problem.
The Problem AI Tools for Small Business Operations Are Built to Solve
Every business I've ever worked with — inside major logistics companies, and now running a couple of my own — hits the same wall eventually. The generic software doesn't quite fit. It's built for an average business that doesn't exist, and you end up bending your operation around the tool instead of the other way around. So people default to spreadsheets, sticky notes, and whatever the last hire remembers about how pricing actually works. That's not a knock on anyone — it's just what happens when the cost of custom software used to mean a six-figure dev contract and a nine-month timeline.
That shift matters because it removes the cost barrier, not the skill required. AI-assisted development — some people call it "vibe coding" — doesn't build a good tool by itself. It still takes someone who understands the business well enough to know exactly what the tool has to do, and the discipline to test it against real jobs before it goes anywhere near a customer. What's changed is that an operator with that kind of judgment no longer needs a six-figure dev contract to act on it. I'm not a software engineer. I'm an operator who's spent a career inside pricing, tenders, network design and commercial execution, and I've spent this year pointing that same problem-solving discipline at the tools my own businesses were missing.
Four AI Tools for Small Business Operations, in Brief
Over the past several months I've used AI coding assistance to build four working applications for businesses I'm personally involved in:
TenderTrail by Sherpa — a pricing and tender workspace built around how freight forwarders actually quote business: origin, freight and destination, priced the way the industry prices it, not the way a generic SaaS template assumes. Capable of importing carrier rates, creating sell-rate methodologies, and generating spot quotes or bids for customers — built off five years' experience overseeing a regional tender management team.
Sunday Pin Estimator — a field quoting tool for Sunday Pin, a painting and exterior cleaning company, that turns a walk-around of a property into a customer-ready proposal without a laptop and a spreadsheet formula nobody else understands.
Waypoint — an operations tracker for my short-term rental business that replaces a scatter of shared spreadsheets. It solves the problems a standard property management system either doesn't address, or charges a lot of money to only partly solve.
Layout and pricing tools for Boma Properties — a connected set of tools built for Boma Properties (bomaproperties.co), the modular container-home company I own, so a layout configures, prices out and visualizes consistently instead of getting redone by hand every time.
I'll walk through each of these in its own post in this series — what problem it solved, roughly how it works, and what it took to build. I'm not going to hand over the pricing logic, the margin structure, or the internal assumptions baked into any of them — those are the parts that are actually worth something, and they stay inside the businesses they were built for.
What I will show you is the shape of the problem and the shape of the solution, because that pattern repeats in almost every operation I've ever looked at.
Why AI Tools for Small Business Operations Matter Beyond Freight
Here's the connection, and it's not a stretch: the businesses that struggle most with freight procurement, network design, and operational execution are usually the same ones running on tribal knowledge and disconnected spreadsheets everywhere else, too. If nobody can tell you your real landed cost by lane without pulling three files together, there's a good chance your pricing on the freight side has the same problem.
Sherpa's core work is freight procurement and bid strategy, supply chain network optimization, transformation and integration, and commercial growth. Building these tools hasn't changed that focus — it's sharpened it. It's a constant reminder that the fix for a messy operation is rarely "buy more software." It's usually building or configuring the one thing that actually matches how the business runs, then getting disciplined about using it.
If that sounds like a familiar problem — on the freight side, the ops side, or both — the rest of this series shows exactly how I've approached it for my own businesses. And if you'd rather skip to the freight conversation, that's what Sherpa is here for.
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