Stormy markets test conviction in ways smooth cycles never do. Jon Novak, chief executive officer of Boomerang Transportation LLC, chose to use a volatile freight cycle to strengthen the company’s core instead of trimming it to survive the moment.
When volumes softened and margins thinned across the industry, Novak and his team made the deliberate decision to double down on internal capabilites—implementing automation, real-time tracking and a disciplined CRM that sharpened visibility for customers. The result was faster communication, fewer surprises and a service experience that gave legacy clients a reason to stay even when uncertainty pulled others to the sidelines. The same decision was made regarding people. Rather than downsize, he trained, cross-trained and rewarded performance, which kept service levels high when speed and accuracy mattered most.
Carrier relationships got the same care. Novak improved partner economics with predictable loads and faster pay, then paired that with consistent communication to build loyalty that shows up in reliability. Through the turbulence the company kept standards firm, which positioned Boomerang Transportation to resume double-digit revenue gains in 2025 and beyond.
Novak founded Boomerang Transportation as a solo operator and grew it into a high-velocity enterprise that nearly quadrupled revenue from 2019 to 2021. Recognition followed. The company earned repeated placement on the Inc. 5000, plus accolades from the Tampa Bay Business Journal for outstanding performance. Novak also invested time and resources in community efforts including support for childhood cancer research, a reminder that stewardship and success can rise together.
A Titan 100 Honoree, Novak leads with a simple credo—see clearly, prepare fully and wait wisely. That mindset shapes the future of work inside the company. Teams are learning to pair data fluency with sound judgment. Automation reduces friction while people handle exceptions with precision. Career paths are visible, leadership development is intentional and skill mobility keeps talent moving toward responsibility rather than out the door.
The five-year roadmap favors excellence over size. Novak intends for Boomerang Transportation to be the most reliable and respected logistics partner in the field, not necessarily the largest. Investment will continue in analytics, software and high-caliber talent. The carrier network will deepen. Service lines will be refined so offerings stay tightly aligned to client needs, and the culture of accountability and integrity will remain the foundation.
The throughline across Novak’s journey is unmistakable—invest when others retreat, honor partners, measure what matters and keep promises under pressure. That steady discipline turned a single-operator startup into an award-winning organization and positioned the company to define how modern logistics should feel for shippers, carriers and teams who value dependable outcomes.
