Future-Ready Fleets: How Leonard’s Express is Driving Efficiency With Smart Technology
Market volatility, downward rate pressure, and rising operational costs mean that staying competitive in today’s trucking industry isn’t just about delivering freight on time. The enterprise trucking companies that are thriving are stepping into the future by embracing new technology.
That’s the story of Leonard’s Express, a family-owned, asset-based transportation provider that operates with a motto of “Lean, Smart, Profitable.” On a recent webinar co-hosted with the Truckload Carriers Association, leaders from Leonard’s Express, Motorcity Systems, and Optimal Dynamics pulled back the curtain on how the organization is using automation, AI-driven optimization, and integrations to drive profitability and efficiency.
So, how is Leonard’s Express setting the standard for data-driven decision-making in 2025 and beyond? You can watch the webinar replay below — or keep reading for a breakdown of the biggest takeaways from the conversation. Have questions? Contact us.
Post-Pandemic Challenges and the Need for Smarter Operations
The trucking industry has faced a harsh wake-up call in the post-pandemic market. The smooth sailing created by high rates and surging demand in 2021 has given way to tight margins and relentless competition. This shift exposed a critical truth: “The revenue that we were generating during the pandemic was hiding a lot of operational sins,” said Kyle Johnson, CEO at Leonard’s Express.
Rather than scrambling to keep up, Leonard’s Express took a proactive approach, recognizing that the key to long-term success wasn’t just blindly cutting costs. The organization needed to optimize every piece of its business by using data and finding ways to automate smarter decision-making.
By integrating advanced optimization technology, Leonard’s Express has transformed how it allocates assets, plans freight, and stays ahead of market shifts. The ultimate goal is positioning the fleet for sustained profitability in an unpredictable industry.
But technology alone isn’t the answer. Leonard’s Express also sought out trusted partners, Optimal Dynamics and Motorcity Systems, to support the company’s shift into the future.
Strategic Technology Adoption and Integration
Leonard’s Express recognized from the start that it would need more than in-house resources to build the modern tech stack, processes, and workflows needed for digital transformation. Most important would be the integration of Trimble TMW.Suite with Optimal Dynamics’ Decision Automation Platform.
“We’ve got really talented people on our IT team that very well could have written the integration between the two platforms,” said Chris DeMillo, Vice President of IT at Leonard’s Express. “But I think that was a very important fork we stuck in the road that said, ‘We’re not going to do this in-house. We’re going to partner with some very smart people outside our organization to do it for us.’”
That decision paid off. With Optimal Dynamics’ Decision Automation Platform and Motorcity Systems enabling the integration with Leonard’s Express existing ecosystem of solutions, the company’s operations have transformed in three key ways:
- Enhanced Data Capture & Analysis: Leonard’s Express can make faster, more informed decisions with better visibility into its network.
- Increased Speed & Accuracy in Freight Planning: Data-driven insights allow the team to allocate loads more effectively and minimize inefficiencies.
- Optimized Load Allocation & Driver Scheduling: More efficient assignments mean less wasted time, fewer empty miles, and better driver experiences.
By leveraging best-in-class solutions instead of reinventing the wheel by building in-house, Leonard’s Express has created a smarter, faster, and more resilient operation that’s designed for long-term profitability.
Early Wins and Key Performance Metrics
Investing in technology is one thing — proving its value is another. During this time of transition, Leonard’s Express expected tangible results related to both profitability and efficiency. With Optimal Dynamics’ Decision Automation Platform in place, Leonard’s Express quickly realized measurable improvements across its operations, including:
- 80% Acceptance Rate of Optimized Recommendations: Trusting the system’s recommendations leads to more consistent and efficient decision-making.
- 5% Increase in Revenue Per Total Mile: Smarter asset utilization is directly boosting profitability, ensuring that every mile counts.
- 45% Reduction in Brokerage Booked Loads: Strengthening network discipline and optimizing internal resources has reduced dependency on outside capacity, improving both margins and driver satisfaction.
Kyle Johnson summed up the selection of the organization’s KPIs with one simple question: “Is the system helping us be more disciplined in our network and not sending assets where we don’t want to send our assets?”
Any digital transformation project will come with challenges. The adoption of AI-powered optimization required refining processes, addressing concerns, and ensuring buy-in across the team. Leonard’s Express took an interactive approach, constantly evaluating, adjusting, and fine-tuning so that its team and organization could bridge the gap between innovation and execution.
Change Management: A Critical Success Factor
Technology alone doesn’t transform a business — people do. One of the biggest takeaways from the webinar was that the successful adoption of smart technology requires both new tools and cultural change.
Leonard’s Express recognized the need to ensure that every stakeholder, from leadership to dispatchers to drivers, was on board. To make this transition as smooth and impactful as possible, they took a structured, people-first approach by:
- Appointing an Internal Champion: A dedicated leader served as the bridge between technology and operations, ensuring the rollout aligned with business goals and employee needs.
- Securing Buy-In from Leadership & Frontline Teams: Transparent communication helped demystify the technology and highlight its real-world benefits for employees at every level.
- Following Structured, Incremental Rollouts: Rather than an all-at-once shift, Leonard’s Express phased in new tools, allowing teams to adjust, provide feedback, and optimize processes along the way.
“That was the biggest thing, making sure that we had the buy-in,” said Kyle Johnson. “From not only upper management but also the decision-makers on the floor.”
This approach accelerated adoption, minimized friction, and delivered measurable results faster than expected. With a strong foundation in place, the company is now looking to scale its technology-driven approach across its entire fleet.
Looking Ahead: Scaling for the Future
As Leonard’s Express moves into 2025, the company is focused on extending the benefits of AI-powered optimization across its entire network. This means:
- Greater Fleet-Wide Efficiency: Leveraging automation and optimization across all operational segments to reduce empty miles, streamline planning, and improve service levels.
- Improved Service Quality: With smarter load assignments and more precise scheduling, regional operations can match the efficiency gains already seen in long-haul trucking.
- Continued Adaptability: The industry isn’t static, and neither is Leonard’s Express. Their commitment to innovation ensures they stay ahead of market shifts while maintaining operational flexibility.
Their journey highlights a key lesson for the industry: Technology is only as valuable as the strategy and teams behind it.
While many fleets struggle with fragmented systems and outdated processes, Leonard’s Express provides a real-world roadmap for embracing automation without sacrificing agility. By choosing the right partners, implementing with purpose, and keeping people at the center of transformation, they’re proving that smart fleets are just as much the present as they are the future.
Want to see how Leonard’s Express approach works in action? Watch the replay of the full webinar, and schedule an Optimal Dynamics demo to learn more.
