Choosing the right Transportation Management System (TMS) can save a small fleet countless hours — or create unnecessary headaches if you pick the wrong one.
I’m Jake, a CDL Class A driver and fleet supervisor, and this guide is built from real-world trucking operations — not software demos or sales pitches.
This is not a ranked list or a “best overall” comparison.
Instead, this is a fit-based guide — matching real fleet sizes and operational styles to TMS platforms that actually make sense.
These tools were selected because they work in real small-fleet environments — not because they have the biggest feature lists.
Best for owner-operators and very small fleets (1–5 trucks)
Trucking365 is built for simplicity. It’s designed for fleets that want structure without complexity.
Good fit if you:
– Run 1–5 trucks
– Want an easy learning curve
– Don’t need advanced automation
– Want something affordable and straightforward
Why fleets choose it:
It solves common dispatch and organization problems without forcing enterprise workflows on small operators.
Watch out:
Limited advanced features - best suited for very small fleets or owner-operators.
Best for structured small fleet operations (3-15 trucks)
Axis TMS is designed for small fleets that need more organization and consistency without jumping into enterprise-level software.
Good fit if you:
- Run 3–15 trucks
- Dispatch loads regularly
- Need more structure than spreadsheets or basic tools
- Want a system that scale with your fleet
Why fleets choose it:
Axis focuses on bringing structure and visibility to small-fleet operations, helping carriers manage dispatch and workflows more consistently as they grow.
Watch out:
May feel like more system than necessary for single-truck or very part-time operations.
Best for flexible workflows and hands-on dispatch teams (5–25 trucks)
AscendTMS offers more customization for fleets that want control over how dispatch and operations are managed.
Good fit if you:
- Run 5–25 trucks
- Have dispatch or admin staff
- Want customizable workflows
- Don’t mind setup time
Why fleets choose it:
Ascend TMS offers easy-to-use automation and insights that help fleets run more effiently and scale smoothly.
Watch out:
More flexibility means more configuration up front.
Best for automated, all-in-one fleet operations (10–50+ trucks)
Truckpedia is designed for fleets that want less manual work and more automation as they scale.
Good fit if you:
- Run 10–50+ trucks
- Want automated workflows
- Prefer guided setup and structure
- Want fewer tools and less manual admin work
Why fleets choose it:
Truckpedia emphasizes automation and operational guidance, reducing repetitive tasks and hands-on management.
Watch out:
May feel structured if you prefer full manual control over every process.
Most small trucking fleets can expect to pay $30–$150 per truck per month, depending on features and fleet size. Some platforms offer flat monthly pricing for very small fleets, while others scale as trucks are added. The right TMS should save more time and money than it costs.
Not always — but once you’re juggling dispatch, paperwork, billing, and driver communication, a TMS can quickly pay for itself by reducing mistakes and saving time.
Buying software that’s too complex too early. Many small fleets overbuy features they’ll never use, which creates friction instead of efficiency.
Yes. Most small fleets switch at least once as they grow. Choosing a TMS that fits your current stage — not your “future fleet” — usually leads to better results.
Some links on this page are referral links. I only recommend tools that I believe are a strong fit for small trucking companies.
A TMS should reduce stress, not add to it.
If it feels heavy, confusing, or overwhelming during the demo — it won’t get better after you sign.