Running a small to midsize trucking operation — typically 10 to 50 trucks — comes with unique challenges. Fleet owners and operations managers often juggle dispatch, billing, driver communications, and paperwork across spreadsheets, phone calls, and multiple disconnected systems. These manual processes may be manageable with a handful of trucks, but as your fleet grows, they create inefficiencies, errors, and wasted time.
For years, many small carriers assumed that a transportation management system (TMS) was only necessary for large airlines with hundreds of trucks. However, that “too small for a TMS” myth is no longer accurate. Modern TMS platforms — such as Carrier1 — are built not only for larger carriers but for fleets in the 10- to 50-truck range. They centralize operations, automate repetitive workflows, and provide real‑time visibility — benefits that directly impact efficiency, cash flow, and scalability.
With increasing pressure on the industry — tight margins, driver shortages, and customers’ rising expectations for shipment visibility — now is the perfect time to invest in a TMS. Many shippers today expect carriers to offer digital load tracking, EDI capabilities, and accurate invoicing. In this guide, we break down seven actionable steps to help small fleet leaders evaluate and select the right TMS for their operation — giving you the clarity to make an informed decision with confidence.
The first step in choosing a TMS is to take an honest look at your current workflows and identify bottlenecks. Ask yourself and your team:
For many small fleets, common pain points include:
Once these pain points are clear, define which features would directly address them. For example:
It’s also important to consider fleet size fit. Systems designed for 500+ trucks often include features small fleets don’t need — resulting in unnecessary complexity, cost, and training overhead. Instead, look for solutions proven with fleets in the 10- to 50-truck range. Carrier1, for example, is built with features tuned to small to midsize carriers — giving you what you need without excess overhead.
By clearly understanding your pain points upfront, you’ll have a sharper lens when evaluating TMS options, ensuring you focus only on those that address the real problems and skip what you don’t need.
Ease of use matters — especially for a small fleet operation. In most small fleets, you don’t have a dedicated IT department or tech staff. The software you choose must be intuitive and easy for your team to learn and use, with minimal onboarding burden.
When evaluating a TMS during demos or trials, look for:
Carrier1 emphasizes simplicity. The one-click workflows, intuitive menus, and straightforward navigation enable dispatchers and drivers to adapt within days — not weeks. That kind of ease of use reduces downtime, decreases the risk of adoption failure, and lets your team focus on work that moves freight rather than wrestling with software.
Automation is not a “nice to have” — for small fleets, it’s essential. When your team wears multiple hats (dispatcher, billing clerk, ops manager), automating repetitive tasks can dramatically increase efficiency and free up time for higher-value work.
Some of the most valuable automation features include:
A practical guideline: Aim for a TMS that automates about 80% of routine operations, leaving only exceptions or special cases to manual handling. This 80/20 rule ensures that the system lightens your daily burden — not creates new complexity.
The productivity gains can be substantial. For instance, one Carrier1 user running under 30 trucks increased load volume by 30% with no additional staff, simply by leveraging automated dispatch-to-billing workflows. That’s more loads, more revenue — and less overhead.
Carrier1 links dispatch information directly to billing and driver pay. Once a load is marked complete, invoices can trigger automatically, driver pay can be generated, and settlements started — cutting out redundant data entry, reducing errors, and improving cash flow.
A TMS should not operate in isolation. Your fleet likely relies on a variety of other tools and services — ELD devices, GPS/telematics, load boards, accounting, fuel cards, factoring partners, and safety compliance systems. Choosing a TMS that integrates smoothly with these tools is critical to avoiding data silos and wasted effort.
Here are key integrations to look for:
By consolidating all your tools into one central hub — the TMS — you eliminate the need to log into multiple portals every day. Carrier1, for example, offers out-of-the-box integrations with ELD providers, supports EDI for shipper systems, and provides a marketplace for fuel and factoring — enabling small fleets to manage dispatch, tracking, billing, and payments all from a single platform.
This level of real-world integration is often a game-changer for small fleets, saving countless hours and avoiding costly mistakes that come from rekeying data across systems.
Even the best software is worthless if your team never adopts it — so easy onboarding and strong support are critical. For a 10- to 50-truck fleet, downtime or confusion during rollout can be very costly.
When evaluating a TMS, ask about:
If available, using a trial or pilot program is highly valuable. Running the TMS with a small subset of trucks or loads for 30 days gives your team hands‑on experience before fully committing. Carrier1 offers onboarding assistance and ongoing support — giving small fleets a partner, not just software. That support often makes the difference between a smooth rollout and months of frustration.
Every small fleet runs on tight margins — so understanding the cost and potential return on investment (ROI) of a TMS is critical.
Most small‑fleet TMS platforms charge a per-truck or per-user fee. For a 10- to 50-truck carrier, expect somewhere in the range of per-truck monthly fees or a small flat-rate subscription. Avoid enterprise-level pricing models designed for 500-plus truck fleets.
Be sure to consider not just subscription fees, but also:
Here are the main areas where a TMS can pay for itself:
For example, if your old manual system limited you to 100 loads a month, a TMS might allow you to reach 130 loads with the same team. Those extra 30 loads — minus TMS costs — represent a direct net gain.
Building a simple ROI spreadsheet can help: List your monthly TMS cost, then estimate time savings, additional loads, avoided errors, and improved cash flow.
A good TMS isn’t just for today — it should grow with your fleet. If you expect to expand beyond 50 trucks over time, choose a system that supports additional users, trucks, and modules like maintenance, HR, or compliance. Cloud-based solutions are often best because they update automatically (for example, for new ELD regulations), and you avoid investing in on-premise servers or IT infrastructure.
Carrier1 is cloud-based, scalable, and built to evolve with you — making it a practical long-term investment even if you grow over the next several years.
Beyond features and pricing, the right TMS must align with your company culture, size, and growth goals.
Choosing a TMS isn’t just about buying software — it’s about selecting a partner for your fleet’s growth, efficiency, and future success.
Choosing the right TMS for a 10- to 50-truck fleet doesn’t have to be overwhelming. By following these seven steps — identifying pain points, prioritizing usability, leveraging automation, ensuring real-world integrations, evaluating onboarding and support, calculating cost and ROI, and confirming cultural and size fit — you’ll be able to evaluate vendors objectively and confidently.
Don’t skip the demos, involve your team, and test workflows that mirror your real operations (dispatch, delivery, billing, driver communication). A fully informed decision — based on how the TMS performs with your actual needs — will pay off far better than choosing based on flashy features or low upfront cost alone.
For many small to midsize carriers, a modern, cloud-based system like Carrier1 offers a compelling mix of simplicity, automation, strong integrations, fast onboarding, and long-term value — exactly what a 10- to 50-truck fleet needs to thrive without overburdening staff or budget.
With this checklist and clear decision framework, you’re well-equipped to step confidently into a TMS evaluation. The right choice can transform your operation, streamline your workflow, eliminate chaos, and allow your fleet to grow efficiently — turning the daily grind of spreadsheets and phone calls into a well‑organized, scalable, and profitable business.
Take a look at Carrier1 TMS, which brings order to your operation and helps your 10- to 50-truck fleet run like a well-oiled machine!
With a modern TMS, you’re never flying blind. You instantly know whether your fleet is running on time, your drivers are being utilized efficiently, and your costs are under control.
