September 23, 2026 · 6 min read

Small Trucking Company TMS: Software Guide for 2-20 Truck Fleets (2026)

With 2-20 trucks, you've outgrown a notebook but you're too small for the software the big carriers buy. Most TMS products are built for fleets of 100+ trucks with an IT department.

You have four real options: a free spreadsheet template, a custom Google Sheets system, small-fleet SaaS, or enterprise TMS. This guide covers what each costs, who it fits and how to choose. One disclosure first: I build the custom Google Sheets systems, so weigh that section accordingly. Everything in it comes from one live system at Winetoast Carrier.

Why enterprise TMS doesn't fit a small fleet

Cost. $200-500/month per user, $10,000-50,000 to set up, and $50,000+ if you want your invoice formats matched.
Time. 2-6 months before your team uses it fully.
Features you'll never touch. Fleet optimization for 200 trucks, but generic invoice formats and a complicated driver app.
Contracts. Long terms, enterprise-focused support and lock-in.

What you actually need

Must-haves: load tracking and dispatch, invoices your customers accept, a customer and billing database, basic fleet records, and a way to reach drivers.

Nice to have: each customer's exact invoice format, driver web pages, live load status, financial dashboards, phone access.

A realistic budget: under $5,000 up front, under $200 a month, and running within 2-4 weeks.

Your options by fleet size

Fleet	Usually running on	Main need	Options that fit
2-5 trucks	Excel or paper	Organization, clean invoices	Free Google Sheets or Excel template
6-10 trucks	Spreadsheets that are straining	Time back, fewer errors	Custom Google Sheets system, small-fleet SaaS
11-20 trucks	Office staff, sometimes more than one location	Room to grow, customer service	Custom system, mid-market TMS, or a mix

Option 1: Free spreadsheet templates

Best for: 2-8 trucks, tight budgets, getting organized. Cost: Free. Setup: 2-4 hours.

A good trucking spreadsheet template covers loads, invoices, customers with payment tracking, and the fleet. The trade-off is manual entry: about 30 minutes per invoice, and basic reports.

	Google Sheets	Excel
Collaboration	Real-time, several people	Limited
Backup	Automatic, in the cloud	Manual
Phone use	View and edit	Limited editing
Offline	Limited	Full
Formula power	Good	Better for complex analysis
Cost	Free	Licenses for each user

Against paper, a template saves a 5-truck fleet 5-8 hours a month for an afternoon of setup. Mine comes in Excel and Google Sheets versions; the Excel setup guide walks through it, and this guide shows how to build your own.

Option 2: Custom Google Sheets automation

Best for: 5-20 trucks running 20+ loads a month. Cost: A one-time project fee, quoted after a walkthrough. No monthly subscription. Setup: Usually live in 1-2 weeks.

This is what I build: a custom Google Sheets TMS in Sheets and Apps Script, fitted to how you already work. Winetoast Carrier has run its loads, drivers, invoices and maintenance on a system I built every day since spring 2026. Here's what it does:

Reads rate cons, so loads aren't retyped.
Handles dispatch.
Gives each driver a phone web page per load, where they sign the BOL and upload photos.
Saves invoices and paperwork to Google Drive.
Sends maintenance reminders by mileage.
Shows profit per load and a P&L.

At Winetoast, entering a load went from 10 minutes to 30 seconds. You own every file and script, so there's nothing to cancel and nothing to export.

It isn't the right fit for everything. If you need ELD, load-board or EDI integrations built in, look at the SaaS and enterprise options below.

Option 3: Small-fleet SaaS TMS

Best for: 8-15 trucks, owners who prefer monthly payments and want vendor support. Cost: $50-150/month per user, or roughly $200-600/month for a small fleet. Setup: 4-8 weeks.

Products in this group include TruckingOffice (aimed at small fleets, with IFTA reporting), Axon (trucking-focused, with factoring integrations) and ProTransport (EDI and multi-location support). Pricing is usually per truck or per user, and it changes, so get a current quote from each vendor.

What's good: It's built for trucking, you get phone support and regular updates, and some products, TruckingOffice for one, include IFTA reporting. What isn't: You pay every month for as long as you use it, invoice formats are generic, customization is limited, and there's a learning curve.

Option 4: Enterprise TMS

Best for: 15+ trucks with complex or multi-location operations and real growth plans. Cost: $200-500/month per user. Setup: 3-6 months.

McLeod Software (aimed at 50+ truck operations) and TMW Systems (aimed at complex multi-modal operations) are the familiar names. For a small fleet, that's overkill: a total cost that can pass $50,000 a year, dedicated IT support, and long contracts.

Side by side

	Free template	Custom Sheets system	Small-fleet SaaS	Enterprise
Invoice time	30 minutes	One click	5 minutes	2 minutes
Customer invoice formats	Generic	Matches yours	Limited	Custom
Driver updates	Phone calls	Phone web page per load	Mobile app	Full suite
Who holds your data	You	You, every file and script	The vendor	The vendor
Monthly cost	$0	One-time build, $0/month	$200-600	$1,000+
Setup	2-4 hours	1-2 weeks	About 6 weeks	About 16 weeks

What your freight changes

Operation	What matters most
Dry van	Fast invoicing at high volume for price-sensitive customers
Flatbed and specialized	Detailed paperwork and driver photos of the load
Regional LTL	Multi-stop loads and pickup schedules, where a SaaS scheduler may fit better
Owner-operator services	Driver settlements and percentage pay
Refrigerated	Temperature records and compliance, which need ELD and sensor integrations

USA and Canada

Whatever you choose, ask how it handles the paperwork on your side of the border:

United States: IFTA for multi-state runs, HOS rules and ELDs, DOT audit records, and state permits and taxes.
Canada: GST/HST by province, cross-border documents, provincial rules, and metric/imperial conversion.
Both: USD/CAD invoicing, time zones, IFTA fuel tax and IRP registration, and CSA/DOT safety ratings.

How to choose

1. Measure what manual work costs you now. Take minutes per invoice × loads per month, divide by 60, and multiply by your hourly labor rate. That's your monthly cost. At 40 loads and 30 minutes each, it's 20 hours a month.

2. Work out the payback. Payback in months = (up-front cost + setup hours × your hourly rate) ÷ (monthly labor saved − any monthly fee). Compare options on payback, not on feature count.

3. List every customer's invoice rules. Generic invoices get rejected, and rejected invoices get paid late.

4. Test with real loads. Run a free template for 30 days on actual freight before you spend anything.

5. Include the drivers. If the system only works in the office, drivers keep calling.

6. Plan the switch. Give the team 2-4 weeks to adopt it, and run the old and new systems side by side for 30 days.

7. Ask every vendor four questions. Can I export all my data? How does the price change as I add trucks? Will you be around in five years? Can I reach a person when something breaks?

Two ways to start

Get organized for free. Request the free template and test it on a month of real loads. I'll email it within one business day.
Get a custom build quoted. If you run 20+ loads a month, tell me how your operation works. It's a one-time project fee, quoted after a walkthrough, with no monthly subscription.