For small but growing fleets—those in the 10-to-25 truck range—the road to expansion is filled with both opportunity and obstacles. These companies have already outgrown the “one-man show” stage, but they’re not yet operating with the systems and staff of the bigger players. If you’re in that in-between zone, this is the time to build smart habits that can scale with you.
Let’s explore how to grow a trucking company the smart way—without losing sight of what made you successful in the first place.
build your business like you're twice the size
Growth starts with infrastructure. Before adding more trucks, take a close look at your current systems. Are you still tracking loads in spreadsheets? Do you have standardized processes for dispatch, billing, and maintenance? Investing in basic fleet management tools now will save you time and prevent growing pains down the road.
Scalable processes let you work on the business, not just in it.
Recruit and Retain Drivers with Intention
One of the first pressure points for growing fleets is staffing. More trucks mean more drivers, but hiring is only part of the equation. Holding onto good drivers is what sets strong fleets apart.
Offer consistent schedules when possible. Communicate regularly and transparently. Provide small perks—bonuses, branded gear, or even lunch on Fridays—that reinforce your company culture. You may not have the deepest pockets, but your drivers should know they’re valued.
cashflow: don't grow broke
Expansion requires capital, and it’s easy to run into cashflow issues during a growth phase. Know your numbers. Monitor your cost per mile and understand which lanes, clients, or contracts are most profitable.
Set aside reserves for repairs, down time, and unexpected costs. You want to grow but not at the expense of your financial health.
insurance: not just a cost center
As your fleet grows, so does your risk profile. Now is a good time to evaluate your insurance program to ensure it is keeping pace with your business. A transportation-focused insurance partner can help you move beyond off-the-shelf policies and into options that align with your growth trajectory, whether that’s better coverage, custom deductibles, or planning for captive or loss-sensitive programs down the line.
final thoughts: Steady beats speed
It’s tempting to chase growth fast—but the most successful fleets grow steadily and strategically. If you take time now to build processes, take care of your people, and plan your finances, you’ll be ready for what’s next.
At Joe Morten & Son, Inc., we work with growing fleets every day. If you're ready to expand your fleet the smart way, let’s talk.
Note: These lists are not intended to be all-inclusive.
This material is intended to be a broad overview of the subject matter and is provided for informational purposes only. Joe Morten & Son, Inc. does not provide legal advice to its insureds or other parties, nor does it advise insureds or other parties on employment-related issues, therefore the subject matter is not intended to serve as legal or employment advice for any issue(s) that may arise in the operations of its insureds or other parties. Legal advice should always be sought from legal counsel. Joe Morten & Son, Inc. shall have neither liability nor responsibility to any person or entity with respect to any loss, action, or inaction alleged to be caused directly or indirectly as a result of the information contained herein. Reprinted with permission from Great West Casualty Company.