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Digital Transformation in Transportation – Part 3: Transitioning from On-Prem to the Cloud

As part of our ongoing series on digital transformation in the transportation industry, we’ve discussed the benefits of using software as a service (SaaS) and cloud-based solutions, and highlighted the protection they provide against cyber attacks.

If you’re convinced it’s in your business’s best interests to transition all or part of your operations to SaaS or cloud solutions, you’re in good company! But you might be wondering: how do I get started? We’ve got you covered with an overview of how to begin finding, evaluating and onboarding a provider and solution that will work best for your organization.

Evaluating Your Needs

Whether you’re looking for a ready-to-use TMS or a more customized solution, or perhaps even a hybrid solution that combines both third-party cloud services with on-premise solutions, the first step is to take stock of your business’s current technology and solutions, and investigate your most challenging pain points. Before you start looking for a solution, it’s vital that you understand your needs.

Do you need a digital scheduling tool to better manage staff and asset availability? What about an intelligent routing solution that can save you miles and fuel? What about a TMS equipped to track every order from the moment it’s tendered to the moment freight is delivered? Is it time to ditch paper forms and timesheets and reports in favor of a more unified digital system? If you’re not sure what you need, you may end up with a solution that is overly complex with too many bells and whistles, or too simple a solution that’s unable to scale with your business as it grows.

Begin by asking a few questions that can help determine which cloud-based solutions might meet your needs. “It’s especially vital through this process that you identify third party applications that interact with your TMS, such as accounting systems, ERP systems and customized applications,” says Michael Skraba, a sales support engineer with Trimble’s SaaS conversion team. “Identifying these integrations up front helps ensure a more seamless transition to SaaS/cloud solutions.”

Here are a few thought-starters to aid your evaluation:

  • What technologies do you currently rely on? How old are they?
  • Is your operation managed via several disconnected pieces of software and processes? Would it be helpful to streamline them?
  • How many vehicles do you have and what kind of tech is on board? 
  • What is your budget? 
  • What are your in-house IT resources accustomed to using? 
  • How complex of a TMS do you need? 
  • Has your company’s system been the victim of cybercrime in the past? 
  • Do you handle sensitive customer data? 
  • Did you recently invest in new on-premise hardware?
  • Do you simply need data storage, or do you need an end-to-end solution? 
  • Does your company have any upcoming deadlines, milestones or seasons to consider?

Take time to answer these questions thoughtfully: if you’re not able to accurately diagnose your organization’s current status and future needs, you may end up with a solution that’s not the right fit.
It’s likely you will find that your organization is primed and ready for an upgrade, and staff may be eager to simplify current processes and/or switch to a more modern system. If so, it’s time to start doing some research to find the right provider.

Finding a Provider

Once you’ve done the groundwork, you can start searching for a cloud-based transportation solution provider. A natural place to start is with providers of other solutions your organization is already using – there may be efficiencies from leveraging additional solutions from the same provider, such as an existing familiarity with their user interface, simplified data migration, an account manager who already knows about your unique business needs and more.

When it comes to evaluating potential providers, consider the following questions:

  • What are their qualifications? 
  • How familiar are they with your type of work? 
  • How much visibility do they provide? 
  • How reliable are they? 
  • How much flexibility and agility do they afford you to expand or contract your operation?
  • Do they have third-party security certifications to protect your data?
  • What are your key integrations that need to be migrated to a SaaS environment?
  • What are the benefits you’d receive for the price you’ll be paying?

Questions around security and compatibility are especially important. In the case of Trimble’s solutions, “We are SOC 2 Type 2 compliant and we’ve partnered with Microsoft to ensure security is at the forefront of our solutions,” Trimble’s Skraba says. “In addition to using a variety of third party tools to scan for vulnerabilities and analyze our security posture, we carefully select our partner vendors to ensure future adaptability to a changing security landscape and market conditions.”

For more ideas, check out this e-book from Intelligent Technical Solutions titled “20 Questions You Should Ask an IT Support Company.” Also consider asking peers for their recommendations, or consulting reviews and testimonials from businesses similar to your own on review aggregate websites such as Capterra, G2 or Gartner. Remember, you’re selecting a software and data provider that will power your organization for years to come! 

It’s important to find a great match that will scale along with your business as it grows and evolves. Be sure to ask them about their product roadmap to ensure their future plans align with your needs and vision for your company.

Next Steps

After you’ve identified one or more service providers to pursue, a natural next step is to request a meeting or demo. Before this initial meeting, put together a brief list of your business’ requirements, and/or a “wish list” of features their cloud-based TMS solution should have. Consider how multiple departments will interact with the solution – it may even be helpful to create a short checklist for each department, including accounting, operations, sales and marketing, driver services and IT.

You’ll also want to ask each provider about their ability to integrate with other providers, so you can ensure that the critical integrations you use today in an on-premise environment are available in the cloud. Throughout the process, be sure to consult your responses to the questions you considered earlier to guide your lists, and read this article from the Cloud Industry Forum about the criteria you should consider when selecting a cloud service provider.

When it comes to Trimble’s solutions, for example, “Our sales representatives schedule an in-depth review of everything the prospective customer uses in conjunction with their TMS,” says Trimble’s Skraba. “We also assist with the process of identifying key third party TMS integrations to streamline the migration process.”

When you’ve narrowed down the field to just one provider and are ready to move forward, you’ll initiate a software and cloud migration, transferring data, retraining staff and streamlining applications. With the right provider, this switchover should be relatively painless – read more about how several Trimble customers converted to a cloud-based TMS from a recent blog post here.


The journey to finding the right cloud provider may seem arduous, but the benefits are many: streamlined workflows in a tight labor market, and the agility to dynamically adapt to the ever-changing transportation market. Resiliency, security and flexibility are all key to making the transition.

It’s normal to feel some hesitation when transitioning to a new way of working, but if you’ve done your research and due diligence to select the right provider, you should be able to sleep at night knowing you’ve asked all the right questions and found the right solution for your business.

To learn more about how Trimble Transportation is helping fleets of all types and sizes transition to the cloud, contact us to discuss your needs and arrange a demo.