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IT Tips: How to Convince Management To Invest in Shipping Software

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Convincing management to adopt/invest in a new Transportation Management System can be challenging. But we have some tips on laying out your case in a way that resonates with management.

Benefits of TMS for IT

Whether you are looking for a more robust transportation management system (aka TMS or shipping software) solution than you have now or are trying to implement one for the first time, you are undoubtedly trying to solve several key issues you and your team are having, including:

  • Connecting disconnected departments - With more departments integrated on a single logistics platform, and more data streaming across your network, individual users benefit by having access to more complete and accurate information. 

  • Integrating to existing tools - A good TMS works with most of the business tools you already use (business software, third-party systems, internal apps, etc.) to help you ship smarter and work more productively across all business operations. 

  • Setting up cloud-connectivity - TMS software has primarily moved into the cloud and provides more security and responsiveness. There is no need to download anything with a SaaS solution- simply connect to secure servers through the internet.

  • Improving workflows between customers/carriers - With greater visibility, businesses can share information faster and more efficiently. Vendors, carriers, and shippers can collaborate to work across each other's networks, share transportation assets, and create economies of scale, which means fewer headaches for IT.

  • Situating systems to scale -  A solid TMS is tech-friendly and easily configurable allowing growth. It is also well supported by a responsive customer service team. The system should also support customizations as needed to serve your unique business needs.

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How to Effectively Sell Your Boss on New TMS

To persuade your managerial team to invest in a TMS, you need a comprehensive understanding of how the investment benefits the business. The best way to do that is to:

Collect Data

Telling your boss how much money, time, and effort the new TMS will save only works if you have the numbers to back it up. Collect hard figures whenever you can, such as the number of lost shipments due to inefficiency or the number of hours saved on admin. The more specific you are about the benefits of the TMS, the better your pitch will be. 

Qualify Your Plan

Illustrate the value of your plan by quantifying the negative aspects of your current system wherever possible. Utilize the data you gathered in the first step to figure out approximately how much money, time, and effort your department is losing without a strong TMS solution.


Remember that some executives may not share your concerns or possess the technical background to truly understand the need for the software investment. As with any investment, changing how you describe the technology to decision-makers can make all the difference. 

Abby Ha of WellPCB puts it this way:

"Selling shipping software as a practical tool to solve headaches is a better way of selling the value of shipping software. This can be communicated in your call to action with a simple statement, like - Support our business goals with improved workflows, visibility, and tracking.”


Quantify the Investment

Executives and other decision-makers make their decisions based on value. An appropriate TMS may be costly, but the cost of not utilizing the right TMS can be much higher. Your job here is to illustrate how and why the new TMS is the solution to the company's most significant pain points. 


IncoDocs Co-Founder Ben Thompson explains:

“To get buy-in from decision-makers, management, IT teams and other stakeholders, you must ensure that the value is clearly portrayed. As a potential buyer, you should receive a detailed proposal that can portray potential value to your operations, like:

    • How much time will TMS save your company?  
    • Does the TMS provide additional access? 
    • Does this update allow employees to work while on the road?
    • What specific parts of your processes will the software automate? 
    • Does the software's automation reduce data re-entry and the risk of human errors?
    • Does the new offering provide better insight into key metrics or reporting details? 
    • Does the new software provide better integration capabilities to further automate processes?
    • What does more free time mean for the company? Can more resources be allocated to sales, marketing or building better client relationships?"

Compare Systems/Software

The software expenditure will be easier for your boss to digest if you compare it to other business investments, like machinery, equipment, and vehicles. Don't forget to compare and contrast your chosen TMS with competing software to prove that it is the right choice for the company.

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Utilize Employee Feedback

Odds are, you are not the only one encountering issues with the current system. As in the first step, you need to quantify the pain of your colleagues by showing how your chosen TMS benefits the entire team – from accounting to warehouse staff to salespeople and management. 

Rally Internal Support

Your plan to adopt/invest in a new TMS for your business will have a higher chance of success if you convince other departments, team members, and managers to support it. Demonstrating to your boss that there is a strong demand within the company for a TMS will encourage them to invest and removes some of the concerns they may have about implementing something new to the team.  


This holistic approach has solid value according to
GetVoIP Founder & CEO Reuben Yonatan:

“Good shipping software comes from an all-hands approach to updates. Product, marketing, QA, and other departments all need to have a say on how this update will function so that business leaders can make better shipping decisions. 

Siloing decision-making to the executive board leads to myopia—much better to have a holistic approach, even if it takes a bit longer. The eventual release will be far better than what you would have shipped otherwise.”


As you approach your managerial team, remember that executives are often resistant to change because it is inherently uncertain and, at times, unpredictable. The best thing you can do to alleviate their concerns is to answer their questions with data, examples, and planning. 

Contact FreightPOP Today

From improving the speed and accuracy of logistics to integrating siloed systems and preparing for growth, we fully understand and support businesses implementing robust TMS solutions. If you still need help presenting your case, reach out to our team to learn how FreightPOP can help you detail to management how your company can reach the next level in logistics and supply chain efficiency. 

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