Somewhere between 15 and 30 trucks, most carriers outgrow the setup that got them there: a load board subscription, a factoring portal, an ELD dashboard, a shared drive and a lot of spreadsheets. The next step is a transportation management system (TMS) that ties those together. Picking the wrong one is expensive: you pay for it, you train everyone on it, and then you live with it or go through the switch again.
Here's what to check, in roughly the order it matters for a carrier with 20 to 150 trucks.
1. Does it fit how you dispatch?
Dispatch is where the software gets used all day. Ask to see a full week on the board: every driver, every load, home time and problems, grouped the way your dispatchers are split. Check how fast a load can be entered (ideally from the rate confirmation, see AI load entry) and how a driver change or a reschedule is handled.
2. Can it pay your drivers correctly?
If you have owner-operators or percentage-paid drivers, the weekly settlement is the hardest thing for any TMS to get right. Bring a real statement from last week to the demo and ask them to reproduce it: recurring deductions, escrow, fuel, advances, reimbursements. If they can't, keep looking.
3. Does it connect to what you already use?
- ELD and GPS (Samsara, Motive and others) for truck locations and hours of service.
- Fuel cards for transactions and IFTA gallons.
- Factoring for submitting invoices and tracking what's been funded.
- Email, so rate confirmations and broker conversations don't live outside the system.
Ask which integrations are included and which cost extra. See Ella's integrations for an example.
4. Does it cover the rest of the company?
Dispatch software that ignores safety, maintenance and accounting just moves the spreadsheets to other departments. Check for driver qualification dates (CDL, medical, MVR), inspections and claims, preventive maintenance, fuel and tolls, company documents and reporting by truck, driver and dispatcher.
5. Who owns the data, and can you leave?
Ask exactly how you'd get your loads, settlements and documents out if you left, and in what format. Some vendors make that easy; many don't. With Ella, the question doesn't come up: you own the code and the database, running on accounts in your company's name. See ownership and privacy.
6. How does the price grow with you?
Per-truck and per-user pricing looks small at the start and large three years later. Do the math for the fleet you expect to have, not the one you have today. We walk through it in per-truck pricing vs. owning your TMS.
7. Is it fast?
A page that takes four seconds to load, opened two hundred times a day by five dispatchers, costs hours every week. Click around during the demo and notice how long you wait.
8. Can it be changed for you?
Every carrier has a few things it does its own way: a custom field brokers ask for, a report the owner reads every Monday, a status nobody else uses. Ask whether the vendor will build those for you, how long it takes and what it costs, or whether you'll be told to work around them.
9. Migration, training and support
- Migration: will they move your history (loads, customers, drivers, settlements) and how many years of it?
- Rollout: can departments start one at a time, so dispatch doesn't stop while accounting learns?
- Support: who answers when something breaks on a Friday night, and what does it cost after the first months?
Red flags in a demo
- The demo uses only perfect sample data and never shows a messy real load.
- Settlements are "coming soon" or handled by an export to another program.
- Basic integrations are priced as separate add-ons.
- Nobody can say how you'd export your data.
- The price per truck goes up at renewal and the contract doesn't cap it.
Where Ella fits
Ella is a custom TMS for carriers with 20 trucks or more. It's built for one company at a time, with your name and logo, and you own it outright. The base system costs $17,000 once and covers dispatch, tracking, fleet, safety, maintenance, fuel, settlements, documents, reporting and recruiting. Add-ons include driver apps, Gmail with AI rate negotiation, Google Chat and Slack alerts, IFTA, multi-board load search and AI dispatch. The first three years of your history are migrated free.
See the product tour, check the pricing, or request a demo and bring last week's settlement.
Frequently asked questions
What is a TMS in trucking?
A transportation management system is the software a carrier runs its business on: loads and dispatch, drivers and trucks, documents, billing, factoring and driver pay, ideally with safety, maintenance and reporting in the same place.
When does a trucking company need a TMS?
Usually somewhere between 15 and 30 trucks, when spreadsheets start causing settlement errors, lost documents and dispatch mistakes, and when nobody can quickly say what each truck earned.
How long does it take to switch TMS?
It depends on the vendor and how much history you move. Ella's build takes three months: the base system runs in the first 30 days, then each department is onboarded in turn, with three years of history migrated free.
What's the best TMS for a small trucking company?
The one that fits how you dispatch and pay drivers, connects to your ELD, fuel cards and factoring, lets you keep your data and doesn't get much more expensive as you grow. Use the checklist above in every demo.