What we learned building a TMS for 10 years. And why we had to start over.

For the past 10+ years I’ve dedicated my life to building a cloud TMS. The wonderful people at Rose Rocket and I have obsessed over how to build a modern, connected TMS. Along the way we had the privilege of helping over 1200 customers, releasing features bi-weekly (sometimes daily), and watching the cloud-native evolution of transportation fully play out.

We were one of the first of this new wave of TMS businesses trying to evolve our very stagnant industry. Over the past ten years, we and others (Alvys, Tai, Revenova, Turvo, et al.) did our best to make sure we helped our customers run their business in the cloud, getting new features frequently (through the power of SaaS) and generally helping the transportation sector get better, faster and stronger.

However in late 2022, we found ourselves having an existential crisis (which timed poignantly with the first early release of ChatGPT). No matter how advanced, the TMS as a category still forced businesses into rigid workflows, disconnected systems, integration creep and manual tasks. So in 2023, we made a bold decision: we disrupted ourselves.

We rebuilt everything again, which we now call the Rose Rocket Platform—a flexible, modular foundation to build a better TMS. It is a better way to run a business. And with it, we unlocked the next evolution: AI-native transportation software.

Introducing TMS.AI: The Next Generation of Transportation Software

Firstly, I believe AI is a seismic shift on par with the agricultural and industrial revolutions. It feels hyperbolic to state this, however, this is the first time in human history we have created a tool that mimics what is distinctly human: our power of thinking.

However, today AI has a dirty secret when it comes to business applications. In 2025, AI hallucinates – providing false, misleading and unreliable information based on a lack of complete context.  It’s not if, it’s when. So how can a business trust these powerful, world-changing tools?

Unlike generic AI tools, TMS.ai has been designed from the ground up to reduce, minimize and evolve around the limitations of today’s technology while setting up our vision to adapt to the artificial intelligence future.

Our Approach

Most AI tools in logistics fail because they are standalone solutions, disconnected from operations, often hardcoded for one particular task, and are inflexible to the realities of the businesses they aim to help. They lack your business’ context, leading to unreliable insights and unnecessary complexity.

TMS.ai changes that by building AI natively into the system-of-record, ensuring:

• Less manual work.
  For example: our DataBot product automates data entry, Rosie optimizes backhauls, and AI-driven invoicing reduces errors because they all have access to the core workflows, data models, and historical data.
• Reliable execution.
  Every action goes through verification, visibility, and validation—reducing hallucinating while increasing trust. While we are still in the first inning of this framework, we believe that it sets up our core platform to evolve with the underlying tech evolve.
• Smarter decisions.
  TMS.ai learns from your operations, improving load-matching, route planning, and pricing strategies, among so much more.

This is the start of the next decade of our company. I’m deeply excited for what is coming and to continue trying to build the best damn transportation software ever. I know we will never be perfect, and I want to thank all our customers, past, present and future for putting their trust in us. We are far from perfect, but everyday everyone at Rose Rocket shows up trying to do better than the day before, learning from our mistakes and showing up ready to commit to building the future.

We’re unveiling TMS.ai at Manifest 2025 in Las Vegas on February 10. But this is bigger than a product launch. This is about reshaping the logistics industry. About building technology that empowers businesses rather than forcing them to work around it.

The TMS as we knew it is dead. TMS.ai is the future.
Visit www.tms.ai to learn more.

Thank You

‍Justin Sky, co-founder and CEO of Rose Rocket

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FYI: What This Means for…

For Current Customers:  

• Classic TMS users: No changes—just a smarter system when you’re ready.  
• Platform users: TMS.ai is now available to you automatically.  

For New Customers:  

• No more choosing between outdated TMS systems or AI tools that don’t understand logistics. TMS.ai is built to scale, automate, and evolve with your business.

For the Logistics Industry:  

• AI in logistics isn’t the future—it’s here. Those who adopt it will gain a real, measurable competitive advantage.

Book a demo with our team if you want to talk about how TMS.ai can help your business.