‍Truckstop, founded in 1995, built the internet’s first digital load board and is now one of North America’s largest freight marketplaces, connecting tens of thousands of carriers and brokers. The company has posted double-digit growth for years and has been profitable every year of its existence – a testament to its enduring success. In many ways, Truckstop is doing what I hope to do with TrueNorth: help carriers and brokers find and book freight, supported by the tools and data that make it easier to run a trucking business.

Like any founder admiring an industry leader, I can’t help but wonder: Could I have done better? I ask myself questions like:

• Could we have built something more defensible or differentiated in the market?
  
  
• Could we have acquired more customers more quickly?
  
  
• Could we have simply executed certain strategies more quickly?

Of course, steering a company of 1,000+ people is no small feat. Changing the direction of a large organization is hard. It’s the job of the CEO to “see around corners” – to adapt quickly when the industry shifts or new technology appears. Truckstop has been an industry leader for almost a quarter century, and as the industry adopts new technologies and changes, there’s a unique opportunity to push things forward through innovation. So, if I were in Truckstop’s CEO, how would I harness that opportunity?

1. Offer a Free Tier for Vetted Carriers to Drive Adoption

One bold move would be to launch a free-tier load board offering for carriers, with proper vetting to maintain quality. Today, most load boards (including Truckstop and its main competitors) charge subscription fees – for example, Truckstop’s basic plan for carriers costs about $42 per month. This paywall can be a barrier for small trucking companies or new owner-operators. Meanwhile, new entrants like TruckSmarter or us at TrueNorth are shaking up the market by offering a 100% free load board with unlimited searches, bidding, and booking. A free platform is a compelling proposition for carriers on a tight budget, and it’s gaining traction.

Why a free tier? The goal would be to dramatically expand adoption and grow Truckstop’s network moat. In freight marketplaces, network size is everything – the value to brokers grows with every additional carrier on the platform (and vice versa). By lowering the barrier to entry, Truckstop could attract the long tail of small carriers, including those who might otherwise try a free competitor. Of course, “free” in freight tech often comes with downsides like unvetted users and higher fraud risk. That’s why vetting is key: Truckstop already prides itself on having trustworthy, vetted brokers and shippers on its paid platform. A free tier could maintain this standard by requiring carriers to pass compliance checks (authority, insurance, safety records) before accessing loads. This way, quality and trust remain high even as the user base grows.

Executing a free tier isn’t trivial – it would mean rethinking Truckstop’s revenue model and cost structure. Short-term, it might reduce subscription revenue. But long-term, it could entrench Truckstop as the default network for finding freight. More carriers on the platform means more loads covered and more data collected, which in turn attracts more brokers and shippers. In a $1+ trillion freight industry that’s rapidly digitizing, grabbing maximum market share now could pay dividends later. A free tier would also fend off emerging rivals before they grow too strong. 

2. Build Deep Integrations into Broker TMS Workflows

My next move would be to make Truckstop inseparable from the daily workflow of freight brokers by deeply integrating Truckstop’s tools into the Transportation Management Systems (TMS) that brokers use. Today, many brokerages and 3PLs rely on internal or third-party TMS software (like McLeod, DAT’s products, etc.) to manage their loads and carrier relationships. If using Truckstop’s load board requires a broker rep to log into a separate website or app, it creates friction. The ideal scenario is that a broker’s rep can post a load, search for trucks, and even execute freight matches on Truckstop’s network without ever leaving their TMS screen.

Truckstop has already taken steps in this direction – the company has built APIs and boasts integrations with most major industry software partners, and even launched its own broker TMS (ITS Dispatch). In 2018, Truckstop announced over 60 new partner integrations with other software, aiming to embed its services into broader workflows. However, there’s a difference between having an API integration and truly seamless, “it-just-works” experiences. If I were CEO, I’d prioritize deep, reliable integrations so that brokers see Truckstop as a behind-the-scenes utility rather than an extra step. 

The benefit of deep integration is improved efficiency and stickiness. When Truckstop is embedded in the tools brokers already live in, it becomes part of their muscle memory. They’ll use Truckstop’s load board more often because it’s effortless, leading to more liquidity on the marketplace. It also strengthens Truckstop’s value proposition to brokers: instead of being just a website they occasionally visit, Truckstop becomes an integral feature of their TMS workflow. Moreover, integration can be a defensible moat; once a brokerage has Truckstop wired into its processes and maybe even custom workflows, they’ll be less inclined to switch to an alternative.

To achieve this, Truckstop would likely need to invest in technical product managers and engineers who truly understand broker operations. Integrating into a variety of TMS platforms (some modern, some legacy) is complex. It requires working closely with partners and customers, mapping out use cases, and handling edge cases so that the integration isn’t buggy or limited. 

3. Build or Acquire an AI Dispatcher to Augment Operations

Finally, I would lead Truckstop to embrace artificial intelligence in freight matching and dispatch, specifically by building or acquiring an “AI dispatcher.” The idea is to leverage AI to handle the repetitive, high-volume tasks of matching freight to trucks, so that human dispatchers and broker reps (sometimes called carrier reps or load coordinators) can focus on building relationships and solving complex problems, rather than making hundreds of cold calls a day.

We’re at the dawn of AI tools powerful enough to automate chunks of logistics operations. Startups are already exploring this (like us at TrueNorth). For example, tools like an AI-driven dispatch assistant that will scan load boards, call brokers on your behalf, and verify load details – essentially acting as a digital co-pilot for a carrier dispatcher. Other AI services can negotiate rates with brokers and handle 24/7 load booking calls via intelligent voice agents. This technology can make multiple calls at once, work around-the-clock, and learn preferences over time to improve matches. The value proposition is clear: let the AI handle the grunt work (finding availabilities, making initial contacts, doing paperwork), while humans handle exceptions and build the personal trust that is so important in trucking.

If Truckstop developed or acquired a true AI Dispatch Assistant, it could integrate this capability into its platform for both carriers and brokers. Imagine a carrier’s dispatcher using an AI system: they enter their truck’s availability and preferences, and the AI automatically finds suitable loads (from the site's load board or even beyond), then calls or messages the broker to confirm load details. The carrier just gets a notification: “Load opportunity ready – call this broker to finalize.” On the flip side, a brokerage could use an AI agent to automatically reach out to carriers for a new load, covering lanes faster than a human team alone could.

The end goal is increased productivity and better service. Human dispatchers and broker reps could then spend their time on high-value tasks: nurturing relationships with their reliable partners, negotiating strategic deals, and problem-solving issues that AI can’t handle. In an industry that will always run on relationships, we don’t want to remove the human touch – we want to elevate it. By handling the repetitive 80% of tasks, AI would free up people to concentrate on the 20% that really differentiates a great freight service (like customer service and creative solutions). Truckstop can take the lead on this trend rather than lagging behind it. Given its resources and data (decades of freight transaction data and patterns), Truckstop is well-positioned to develop an AI model for dispatch or to partner with a tech company to do so.

So, what would you do if you were CEO of Truckstop? The above are the three big bets I would place to ensure Truckstop stays on the cutting edge of freight technology: dramatically expand the network via a free carrier tier, embed the platform deeply into brokers’ daily operations, and lead the charge on AI-assisted freight matching. Truckstop has a proud legacy and a strong foundation; with the right strategic moves, it can continue to be the market’s powerhouse even as new tech and new players emerge. As someone building in the same ecosystem, I’ll be watching closely – and learning from what Truckstop does next. After all, the freight industry is changing fast, and every leader in this space has to keep asking themselves how they would steer the ship. Now it’s your turn to think: if you were in charge of Truckstop, how would you drive the company forward?

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‍Check out our original LinkedIn post on this topic (as well as our take in FreightCaviar) and stay up to date on our latest announcements at TrueNorth!