Five Step Guide to Choosing Trucking Software

This guide outlines how to approach the process for selecting the right TMS and trucking software for your business, based on your unique needs. It’s important to keep in mind that there is no such thing as a “best” trucking software for the industry. There are various factors that make certain software options better for your fleet than others. 
Published on
July 17, 2023
min read

This guide outlines the process for selecting the right TMS and trucking software for your business, based on your unique needs. It’s important to keep in mind that there is no such thing as a “best” trucking software for the industry. There are various factors that make certain software options better for your fleet than others: 

  • What types of loads do you haul? 
  • Are you 100% load-board driven or do you mostly run dedicated lanes? Short-haul, long-haul, both?
  • Do you need a way to take order requests online? 
  • Do you receive a lot of check calls? 
  • Do you want to meld something to your current way of working, or are you open to reimagining how software may improve your overall business and operations based on innovative designs?

Step 1: Map out how your team is structured and the key “jobs to be done” in each function.

Typically, we see trucking organizations revolve around five core functions: customer relations (sales), dispatch, operations & finance, maintenance, and compliance. In large fleets, these tend to be distinct teams. In smaller fleets, fewer team members tend to wear multiple hats, so you might have one or two team members working on booking loads & dispatch and a few team members covering all other operations.

Regardless of your team’s size, the first critical step is to simply list the key tasks and responsibilities of each of your functions. We recommend doing this as a team, using sticky notes on a wall or making notes on a whiteboard. You often will surprise yourself with a number of gaps and areas for improvement. Even ahead of selecting software, this process can reveal eye-opening improvement areas for your team to get more efficient and be more effective in working together.

Step 2: Map out how you work today.

Here is a list of questions to go through while mapping out your current workflow:

  1. With sticky notes, write out every step from first contact with a shipper all the way through delivery and payment. The full closed loop.
  2. For each step, who on your team owns it? We suggest writing the name of the responsible individual next to each of the key steps 
  3. What systems and tools do you use today? List them all out, from ELDs to software to accounting to compliance. Are you using an outdated TMS, working off whiteboards and Google Sheets, or have you cobbled together a variety of point solutions?
  4. How are you handling dispatch? Are you using WhatsApp or text messages, white boards and phone calls?
  5. How do they tie together, or not tie together? 
  6. What are the biggest gaps or frustrations with your overall system? What does your team like, and what don’t they like?
  7. How do you assign loads?
  8. How do you handle billing and invoicing? 
  9. How do you handle driver pay? 
  10. What are the time-consuming manual steps? Where are errors most likely to appear?
  11. What do you like, what don’t you like? 

Step 3: Identify your goals and get clear what you’re solving for.

If you don’t know what you’re solving for, you’re unlikely to be satisfied with a software implementation. Go through the following list and develop a short description of your goals and timeline for a software system.

Are you trying to…

  • Scale from 5 to 50 trucks, and looking to support growth?
  • Increase visibility into your operations?
  • Find ways to decrease costs? 
  • Save wasted time?
  • Invoice faster, so you get paid faster?
  • Enable remote work and collaborate with team members?
  • Ensure your staff doesn’t get burned out?
  • Have a unified tool that your team can all work in simultaneously?
  • Professionalize your business and impress customers? 

Once you have identified the top 3-5 priorities, you can then start to identify solutions. We recommend writing this down in 1-2 sentences, so you have a clear sense of what your goals are.

Here are a few examples of statements of goals and how they map to potential software solutions: 

“I’m looking to support our growth from 5-50 trucks, and move off of cobbled-together tools without breaking the bank or getting bogged down in a lengthy implementation process.”
  • Look for a clean, simple, all-in-one solution that is built on a modern tech stack (so it can scale with you). Solve for the next 2-3 years.
  • For a 5-50 truck fleet with a small office staff, you want a manageable implementation process and timeline. It should be 1-4 weeks for a fleet this size, depending on your current operational complexity. 
  • Enterprise-grade solutions like McLeod are best for fleets with hundreds of trucks, and can take many months of hands-on implementation work to customize the solution for you. For smaller fleets, this is overkill and very expensive.
“My business is increasingly based on direct relationships with customers as opposed to solely relying on load boards. I’m looking to professionalize and build trust with customers, and I want to get more dedicated lanes with a few major brokerages.”
  • Look for a solution that has a customer portal and live tracking. Being able to leverage that degree of visibility, transparency, and proactivity is a great way to build trust and deepen those relationships.
  • You can also differentiate your carrier with a software that automates check calls and sends the proof of delivery within minutes of each completed load. Major brokerages often track this, and it can improve your carrier rating.
  • You may want to look for a system that has EDI integration capabilities. EDI stands for Electronic Data Interchange, and it’s a way for your software to automatically communicate with your customer’s system (e.g., order requests, location tracking, and invoicing).
“Manual data entry takes time away from booking loads, and duplicating data across systems means lost BOLs and loads”
  • Your software tool should save countless hours with automating order entry, as well as billing, invoicing work.
  • Be sure to ask software providers how they are leveraging AI to optimize this process – the best providers have found ways to harness AI to make the process even faster and smoother.
  • If you use accounting software like QuickBooks, then you’ll want to make your systems integrate seamlessly. You might consider switching from QuickBooks Desktop to QuickBooks Online as well because integrations are typically better with QuickBooks Online.
“As we grow, dispatching and communicating with drivers is getting too painful. I need a system to manage it all in one place.”
  • Text-based dispatch that is driven by your software system tends to be the easiest to use. Forcing them to download apps or keep track of passwords is time-consuming and can be frustrating. 
  • Keep in mind that your drivers are the lifeblood of your trucking business, so it is critical that any new system is easy and reliable for your drivers.

Step 4: Do your homework. You’ll want to evaluate TMS options along three core pillars: dispatch, invoicing, and settlements. 

It’s possible to spend over $100,000+ on trucking software if you want a highly customized suite that has enterprise features you’ll ever need and can help you scale to 500+ trucks. If you’re a smaller fleet, there are several options that are dynamic, cloud-based, and adaptable as you grow from 5 to 50 trucks and beyond. 

For a few helpful lists of trucking software, here are three worth reviewing:

One thing to keep in mind is ease of use and implementation. The worst software is the one that doesn’t get used because your team can’t figure it out. For smaller fleets especially, ease of use is directly related to how successful a new software will be for your team.

As you review different trucking software providers, here are a few areas to evaluate. Keep in mind what your goals are. For the areas you’re looking to improve the most, does a specific provider have great solutions?

Here are a few features to consider for each functional area:


  • Automated order entry
  • Easy-to-use split loads
  • AI tools to decrease manual work
  • Driver texting
  • Driver app

Customer engagement

  • Live tracking & ELD integrations
  • Check call automation
  • Customer portal
  • EDI integrations

Billing invoicing

  • Simple invoicing flow
  • Ability to add fuel surcharges and other costs
  • Ability to send multiple loads per invoice
  • QuickBooks integration

Driver pay

  • Integrated driver settlements
  • Multiple pay types (percentage, cent per mile, stop pay)
  • Recurring bonuses & deductions
  • Owner operator & company driver support
  • Fuel card integrations


  • Maintenance cost tracking
  • Truck out of service tracking
  • Preventative maintenance reminders


  • Driver qualification file storage
  • Expiration & renewal reminders


  • Powerful search functionality, including lane search
  • Performance reports for trucks, drivers, and dispatchers

Step 5: Evaluate partnership with the specific team you’re working with at the TMS company.

When selecting a trucking software provider, the team you have access to is critical. Are you going to be handed off from a salesperson immediately after you sign? Have you met and vetted your account manager? Do you have access to a contact who can resolve issues as they arise?

It is crucial to ask for references and thoroughly examine customer reviews. Choosing a software provider is not just a transactional decision but a long-term investment. The best software providers treat their customers like partners.

Reviewing online feedback from other users offers a broader perspective on the provider's reputation, overall customer satisfaction, and potential challenges. 

Requesting references allows you to gather valuable insights from existing clients, enabling you to assess the software's performance, ease of use, reliability, and customer service. By reaching out to references, you can gain firsthand information about the provider's responsiveness, professionalism, and their commitment to further improvements to the software.

This comprehensive evaluation of references and reviews ensures that you make an informed decision, establishing a strong foundation for a lasting partnership with a trucking software provider that aligns with your business objectives and provides ongoing support and value.

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