TL;DR
When “The Think Small Podcast” titled the episode “The 25-Year Overnight Success,” I laughed. Then I thought about it for a minute and realized it was actually the most accurate thing anyone had said about our company in a long time.
At Infinity Software Solutions , we have been building software for freight brokers since 2000. That is a long time to do anything. And yet, in a lot of ways, we are only now learning how to grow.
I sat down with Denise Steinbring of Chief Outsiders on The Think Small Podcast to talk through that tension honestly: what we built, what we got right, what we underinvested in, and where the company is headed. The conversation covered more ground than I expected, and I came away with a few things worth writing down.
If the player does not load, listen to the episode on Apple Podcasts .
This post is not a recap. It is the article I wish existed when I was trying to figure out how to turn a mature, trusted software company into one that also grows with intention. Here is what that looks like in practice:
Here is something that took me longer to say out loud than it should have: Infinity Software Solutions built extraordinary customer loyalty through BrokerPro for 25 years and historically underinvested in the things that create new growth.
That is not a criticism of the people who built this company. It is an honest description of how most mature software businesses operate. You get good at serving the customers you have. You earn trust through execution. Renewals stay strong. And somewhere along the way, you stop treating growth as a discipline that requires its own system.
Surviving for 25 years in freight tech is genuinely hard
The contrast matters:
What longevity gives you:
What longevity does not give you:
That gap is what the podcast episode was really about. And closing it is what has driven most of the decisions we have made at Infinity Software Solutions over the last two years.
Before I talk about what we are building next, it is worth being clear about why we can build it credibly.
BrokerPro was built from the ground up for freight brokers, not adapted from a generic logistics platform. That specificity is what created the foundation everything else rests on.
Customer longevity tells the story. The median active BrokerPro customer has been with us for nearly five years, and several customer relationships extend over two decades. That kind of loyalty is earned through a product that works, support that responds, and a team willing to keep improving alongside the people who use it. You can hear that directly in our customer stories .
The core of what we got right:
A TMS solves a specific, critical problem: helping brokers execute freight efficiently after the business is won. It is not built to help sales reps find prospects, manage opportunities, close new customers, or guide the full lifecycle of a shipper relationship.
That gap has always existed. What changed is that the cost of ignoring it got higher.
Three shifts drove that:
What brokers actually need is a system where operational data and commercial data live close enough together to be useful. That is the real problem BrokerOS was designed to solve.
We built BrokerOS as a commercial growth layer that complements BrokerPro TMS - or any TMS - because operational excellence alone is not enough to help a brokerage grow.
The product has three components, each solving a distinct problem:
| Component | Core Job | Business Impact |
|---|---|---|
| BrokerOS Web | Standards-driven websites with real-time lead capture and AI-supported content | Get found by shippers who do not already know your name |
| BrokerOS CRM | Automate deal and account management data across the customer lifecycle | Turn relationships into a managed pipeline, not just a contact list |
| BrokerOS Intelligence | Combine data from online sources into a unified warehouse for business decisions | Understand which customers, lanes, and markets are actually worth pursuing |
Together, the three components answer a question that a TMS was never designed to answer: how does a freight brokerage grow its customer base with the same discipline it applies to running freight?
One thing worth noting: BrokerOS was built to work regardless of which TMS a broker uses. That was an intentional decision. We did not want growth infrastructure to be contingent on a platform switch. But for BrokerPro TMS customers, the integration between operational data and BrokerOS is tighter, and that is where the real leverage comes from - the same data that runs your freight operation can inform your commercial decisions without any manual bridging.
That makes Infinity Software Solutions a different kind of software company than we were five years ago.
BrokerPro AI , launched in April 2026, uses CloneOps.ai , an AI-driven business communications platform that embeds intelligent agents in operational workflows. BrokerPro AI lives inside the TMS, not alongside it as a separate login or integration project. The use cases are specific and operational:
We also added Loadsure for embedded freight insurance and Highway for carrier onboarding and compliance to BrokerPro, both available out of the box. The goal with all three is the same: reduce the number of tabs, vendors, and manual steps a broker needs to run a load.
The honest AI take: AI matters most when it removes work that was already happening, not when it introduces a new workflow that requires training and behavior change. Every automation we have shipped targets something a broker was already doing manually. That is the test we apply before we build.
For Infinity Software Solutions, growth means continuing to expand BrokerPro for freight execution while giving brokerages additional commercial tools through BrokerOS.
If you listen to the episode, you will hear Denise push me on the harder questions. Here is what I kept thinking about afterward:
1. Loyalty is earned operationally, but growth must be built intentionally. Customer retention does not happen by accident in freight tech - it happens because the product works and the support is real. But new customer acquisition does not follow automatically. It requires its own system, its own investment, and its own discipline. Those are two separate jobs.
2. The companies that adapt win by connecting execution, customer lifecycle, and insight. The brokerages I see pulling ahead are not just running freight well. They know which customers are profitable, which lanes are worth pursuing, and which relationships need attention. That visibility requires connected data, not a better spreadsheet.
3. Curiosity matters more than age. A 25-year-old company can still be early in learning how to grow. The question is whether the people running it are willing to examine what they have not built yet. That willingness is the only real competitive advantage that compounds over time.
Infinity Software Solutions has served freight brokers since 2000 and built strong customer loyalty, deep domain knowledge, and a proven TMS. The overnight-success idea reflects the company’s more recent decision to treat growth, discoverability, and customer acquisition as disciplines that need their own intentional systems.
BrokerPro and BrokerOS are products from Infinity Software Solutions. BrokerPro TMS supports freight execution, including carrier management, load execution, tracking, documents, billing, and other operational workflows. BrokerOS supports commercial growth through websites, CRM, and data intelligence. BrokerOS works with any TMS, while using it alongside BrokerPro can create tighter connections between operational and commercial data.
BrokerPro AI uses CloneOps.ai, an AI-driven business communications platform that embeds intelligent agents in operational workflows, to bring automation inside BrokerPro TMS. Its operational use cases include carrier sourcing, check calls, load tracking, collections support, invoice follow-up, and carrier communication.
BrokerPro follows a quarterly release cycle that delivers regular workflow, performance, integration, and platform improvements. Investments such as BrokerPro AI, Loadsure, and Highway continue to expand what freight brokers can do inside the TMS, while BrokerOS addresses separate commercial growth needs.
The full conversation with Denise covers more ground than I could fit here, including some of the specific decisions behind BrokerOS and what it actually looks like to build commercial operations inside a freight-tech company. Worth 30 minutes of your time if this topic is relevant to where your brokerage is headed.
Choose the next step that fits where you are headed:
Listen to Episode 103 Learn More About BrokerPro See What BrokerOS Does
The next chapter for Infinity Software Solutions is about helping brokers run better and grow better through BrokerPro and BrokerOS. Those two priorities are finally part of the same product portfolio.
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