TRUCKING GUIDE

HOW TO SUCCESSFULLY ORGANIZE AND MANAGE A GROWING TRUCKING COMPANY

Running a trucking company isn’t for the faint of heart.

Between managing drivers, keeping up with DOT regulations, maintaining cash flow, and staying competitive in a tough market, fleet owners face constant challenges.

Growth adds another layer of complexity—scaling operations while maintaining efficiency and compliance requires careful planning and the right strategies.

The good news? You don’t have to figure it all out on your own.

In this guide, we’ll share expert insights and actionable tips to help you organize, manage, and grow your trucking company with confidence. Whether you’re just starting out or looking to take your fleet to the next level, these strategies will set you up for long-term success.

Be Your Customer's #1 Trucking Choice | Ryan Good, RGM TRANSPORT

Caution: Wide Right fleet management interviews~

INSIGHTS

HOW TO IMPLEMENT

Know Your Why and Build a Strong Company Culture

It sounds simple: “Know Your Why”, but understanding your deeper purpose is the foundation for building a strong company culture.

As Ryan Garber of GFI Transport put it:

“Do you want to grow your fleet to 20 trucks just because it looks impressive, or is there a bigger mission driving you? Do you want to impact and influence people by creating an environment where people can thrive?”

Defining your “why” not only shapes your business decisions but also influences how your team operates and stays engaged.

A well-defined purpose leads to a culture where employees feel connected to a shared mission. When your team understands why the company exists beyond just making money—whether it’s prioritizing safety, providing reliable service, or being an employer of choice—it builds loyalty and motivation.

And as we know, employee satisfaction directly impacts business success. Setting clear expectations, valuing communication, and fostering professional growth create a positive work environment. A strong company culture helps retain drivers, reduce turnover costs, and build a committed team.

Ideas to strengthen company culture:

  • Host quarterly town hall meetings to encourage open communication and gather feedback.
  • Offer performance-based bonuses to reward hard work and dedication.
  • Recognize outstanding employees through awards, shout-outs, or incentives.
  • Invest in professional development by providing training programs or mentorship opportunities.
  • Celebrate company milestones and successes to foster a sense of pride and unity.

By defining your “why” and creating a workplace where people feel valued, you set the foundation for long-term success—not just in business growth, but in building a trucking company that truly makes an impact.

Plan for Structured Growth with Robust Systems in Place

Growing too fast without proper systems can lead to operational inefficiencies and financial strain.

To prevent this, Ryan Garber of GFI Transport stressed:

“Putting strategic plans together to grow is when things really started to take off for us. When opportunities presented themselves, we took those opportunities but we are now more on the track of being a growing company with a growth mindset while serving our clients and employees really well.”

To take it a step further, Ryan Good at RGM Transport added:

“When you’re growing, we pushed it pretty hard at adding trucks and it caused a lot of turmoil because we didn’t have the systems and processes in place to handle it. If we had that earlier, it would have helped us tremendously.”

So, what does this look like?

Here are some best practices for fleet managers to handle growth effectively:

  1. Clearly Define Job Roles and Responsibilities: As your fleet expands, so do the complexities of managing operations. Clearly defining job positions ensures that tasks are handled efficiently and that there’s no overlap or confusion. Key roles to define include:
    • Fleet Manager: Oversees dispatch, maintenance, and compliance.
    • Safety & Compliance Officer: Ensures adherence to DOT regulations and safety standards.
    • Driver Manager: Manages recruitment, retention, and driver performance.
    • Operations & Logistics Coordinator: Handles route planning, scheduling, and fuel optimization.
  1. Hire Strategically to Support Expansion: Growth requires the right team. Bringing on key personnel like dispatchers, safety managers, and financial advisors can help manage expansion efficiently. Hiring additional drivers should be balanced with fleet growth, ensuring there’s enough work to keep them busy while maintaining profitability. A good hiring plan involves:
    • Conducting background checks and road tests to ensure driver quality.
    • Offering competitive pay and benefits to retain drivers.
    • Implementing an onboarding program to familiarize new hires with company policies.
    • Maintaining an optimal dispatcher-to-driver ratio to avoid operational bottlenecks.
  1. Establish Standard Operating Procedures (SOPs): Having robust, repeatable processes is crucial for consistency and efficiency. Planning should also include setting KPIs (Key Performance Indicators) to measure operational success, such as fuel efficiency, driver retention rates, and delivery times. SOPs should cover:
    • Driver onboarding and training to ensure new hires understand company policies and safety regulations.
    • Maintenance schedules to prevent unexpected breakdowns and DOT violations.
    • Dispatch and load planning to optimize routes and minimize deadhead miles.
    • Billing and invoicing processes to improve cash flow and minimize payment delays.
  1. Invest in Fleet Management Technology: Leveraging technology can help streamline operations as you scale. Consider:
    • Transportation Management Systems (TMS) for optimizing load assignments and tracking shipments.
    • Electronic Logging Devices (ELDs) to ensure compliance with HOS regulations and monitor driver performance.
    • GPS tracking and telematics for real-time vehicle monitoring, fuel management, and safety analytics.
  1. Optimize Recruiting and Retention Strategies: A growing fleet requires a steady pipeline of qualified drivers. Best practices include:
    • Offering competitive pay and benefits to attract top talent.
    • Creating a strong company culture that prioritizes driver well-being and work-life balance.
    • Implementing mentorship programs where experienced drivers help train new hires.
  2. Maintain Compliance as You Scale: Regulatory requirements increase with fleet size, making compliance even more critical. Stay ahead by:
    • Regularly auditing safety and compliance procedures.
    • Training staff and drivers on the latest FMCSA regulations.
    • Using compliance software to track driver qualifications, vehicle inspections, and reporting deadlines.

By implementing these best practices, fleet managers can create a solid foundation for growth while maintaining efficiency, profitability, and compliance.

Financial Planning is Essential

Financial planning is essential for trucking companies at any stage—whether you’re starting out with a single truck or expanding your fleet. Trucking is a cash flow-intensive business, with high upfront costs, ongoing expenses like fuel and maintenance, and unpredictable payment cycles. Without a strong financial strategy, even profitable companies can run into trouble.

Ryan Good of RGM Transport highlights the importance of financial planning:

“The other big thing is we have advisors now for the financial end of it. They help us get onto a budget, manage slower periods, and more. I wish we would have had these advisors, coaches, or mentors earlier.”

Having financial advisors or mentors can make the difference between a trucking company that thrives and one that struggles with cash flow challenges. Below, we’ll explore why financial advisors are critical and provide best practices to help trucking companies manage growth effectively.

  1. Managing Cash Flow & Budgeting: Trucking companies often face delayed payments, with brokers and shippers taking 30 to 60 days to pay invoices. Meanwhile, expenses like fuel, insurance, and payroll require immediate cash flow. A financial advisor can:
    • Help create a realistic budget that accounts for fixed and variable costs.
    • Identify ways to improve cash flow management, such as factoring invoices or negotiating faster payments.
    • Assist in planning for seasonal slowdowns, ensuring you have enough reserves to cover expenses.
  1. Avoiding Costly Debt & Overextension: Many trucking companies make the mistake of overleveraging themselves by financing too many trucks or taking on high-interest loans. A financial advisor can:
    • Help evaluate financing options for new trucks or equipment to avoid risky debt.
    • Provide debt management strategies, ensuring that loan payments align with revenue.
    • Prevent overexpansion, which can strain cash flow and lead to financial instability.
  2. Fuel Cost Management Strategies: Fuel is one of the largest expenses in trucking. Without a strategy, fluctuating fuel prices can eat into profits. Financial advisors can help:
    • Explore fuel contracts or bulk purchasing to lock in lower rates.
    • Recommend fuel cards that offer discounts and improved cash flow management.
    • Identify cost-saving measures such as fuel-efficient routes and idle reduction strategies.
  3. Setting Up an Emergency Fund: Unexpected expenses—such as major truck repairs, accidents, or regulatory fines—can derail a trucking company. A financial advisor can:
    • Guide the company in setting up an emergency fund to cover three to six months of operating expenses.
    • Help allocate a percentage of revenue to a contingency fund.
    • Advise on insurance coverage to mitigate financial risks from accidents or lawsuits.
  4. Optimizing Profit Margins & Cost Control: Profit margins in trucking are often slim, so tracking expenses and revenue is crucial. A financial advisor can:
    • Analyze profit margins on each lane, load, and customer.
    • Identify areas for cost reduction, such as renegotiating contracts or optimizing routes.
    • Recommend accounting software like QuickBooks or a TMS (Transportation Management System) for expense tracking and financial reporting.
  5. Securing Financing for Growth: When expanding, trucking companies need capital for additional trucks, hiring drivers, and securing new contracts. A financial advisor can:
    • Help secure affordable financing options without overleveraging the business.
    • Evaluate the return on investment (ROI) before making large purchases.
    • Assist in building business credit to access better loan terms.
  6. Implementing Efficient Invoicing & Collections: One of the biggest financial challenges for trucking companies is delayed payments from brokers and shippers. A financial advisor can:
    • Implement an efficient invoicing system to ensure timely payments.
    • Recommend factoring services (if necessary) to improve cash flow.
    • Assist in setting up late payment policies and collections processes to reduce outstanding invoices.

By working with financial professionals and following key financial best practices, trucking companies can avoid common pitfalls, plan for sustainable growth, and build a financially strong business that can withstand industry fluctuations.

Position Your Fleet as a Top Carrier

Shippers and brokers prioritize reliability.

In fact, long-term partnerships lead to stable freight opportunities, even during market downturns.

Ryan Good of RGM Transport put it this way:

“We aren’t trying to be the biggest trucking company. We are not even going to try and compete in that space. So, we want to be the best. That doesn’t mean we have to be the best in the U.S., it means we have to be the best in our customer carrier network. So, when you are with a customer, strive to be their #1 or #2 hauling option. If you’re #2, why aren’t you #1.”

Building long-term, profitable relationships with shippers requires a structured customer reminder strategy that keeps your company top-of-mind while respecting their preferences. Here’s how you can implement an effective follow-up system tailored to each customer’s needs:

  1. Categorize Customers by Engagement Level: Segment your shippers based on their frequency of use and potential for growth. This allows you to tailor your follow-up schedule:
    • High-Volume Customers: Weekly or bi-weekly check-ins to maintain strong relationships.
    • Occasional Customers: Monthly or quarterly reminders.
    • Inactive/Past Customers: Semi-annual or yearly follow-ups to re-engage them.
  1. Use a CRM to Track Interactions: A Customer Relationship Management (CRM) system (such as HubSpot, Salesforce, or a trucking-specific CRM) helps organize and automate follow-ups. You can:
    • Log calls, emails, and past shipments.
    • Set reminders for the next check-in based on their preferences.
    • Track the last conversation to personalize future interactions.
  1. Automate Email and SMS Reminders: For less frequent touchpoints, set up automated email or text reminders:
    • A quarterly check-in email: “Hey [Customer Name], just checking in to see if you need any lanes covered. Let us know how we can help!”
    • Personalized seasonal updates, such as: “With peak season coming, we’re here to help with capacity needs.”
    • An annual “thank you” or holiday message to maintain goodwill.
  1. Schedule Personalized Calls Based on Preferences: Not all customers want frequent calls, so ask them directly:
    • “Would you prefer a quick monthly check-in or just a quarterly touch base?”
    • Some may only want outreach when you have capacity in their lanes—use this as an opportunity to present solutions.
  1. Provide Value Beyond Just Checking In: When reaching out, offer something helpful rather than just asking for business:
    • Industry updates or market trends that impact their freight.
    • Lane availability or rate insights that could benefit them.
    • Operational improvements you’ve made that might make working with you even easier.
  1. Keep Notes on Key Customer Details:
    • Their preferred lanes and freight types.
    • Any challenges they’ve faced and how you can help.
    • Their preferred method of communication (call, text, email).
  1. Follow Up After Every Shipment: For active customers, a post-shipment check-in can solidify your relationship:
    • “Did everything go smoothly with the last load?”
    • “Any feedback to improve our service for next time?”

Remember, reputation is everything in the trucking industry. Ensuring on-time deliveries, minimizing breakdowns, and maintaining open communication with customers help build long-term relationships. Even during slow periods, staying engaged with customers keeps your company top of mind.

Ways to enhance customer service include:

  • Implementing a customer portal for real-time shipment tracking.
  • Sending automated status updates via email or SMS.
  • Establishing a dedicated customer service team to address inquiries promptly.

Managing Freight Market Fluctuations

The trucking industry is inherently cyclical, with fluctuating freight demand, seasonal slowdowns, fuel price volatility, and economic shifts affecting profitability.

Fleet managers must proactively manage these fluctuations to ensure long-term business stability and growth.

By strategically planning, maintaining financial reserves, diversifying freight lanes, and staying informed on market trends, trucking companies can weather downturns and capitalize on emerging opportunities.

  1. Understanding Freight Market Cycles: Freight demand naturally rises and falls throughout the year. Successful fleet managers plan ahead to compensate for slow seasons and capitalize on peak periods.

Example: Many fleets increase their contract freight commitments in Q3, anticipating the slower Q1 months when demand traditionally drops. Securing reliable long-term contracts helps maintain revenue during downturns.

    • Monitor industry trends using platforms like FreightWaves or DAT to anticipate freight shifts.
    • Build strong relationships with customers and brokers to secure consistent freight.
    • Diversify freight lanes to balance out seasonal slowdowns.
  1. The Importance of Financial Reserves: Market downturns can strain a trucking company’s cash flow, making financial preparedness essential. Having reserves set aside for lean periods ensures operational stability and prevents financial overextension.
    • Maintain an emergency fund to cover at least three to six months of operating expenses.
    • Optimize fuel purchasing by using fuel cards, negotiating bulk rates, or leveraging fuel hedging strategies.
    • Track expenses closely with accounting software or a Transportation Management System (TMS) to identify cost-saving opportunities.
  2. Staying Flexible in a Changing Industry: The trucking industry is influenced by economic conditions, fuel price spikes, regulatory changes, and supply chain disruptions. Fleet managers who stay flexible and adapt quickly are more likely to survive market fluctuations.
    • Expand into new regions when demand shifts.
    • Exit unprofitable markets if freight rates become unsustainable.
    • Shift business models if necessary, such as pivoting from spot freight to dedicated contracts.

📌 Example: A fleet that primarily hauled auto parts successfully pivoted to medical supply transport during an economic downturn, ensuring business continuity.

  1. Strategic Freight Diversification: Diversification can provide stability during slow periods, but it must be done strategically to avoid overextending resources. Expanding into new freight markets can be profitable if demand supports it and operations are scaled efficiently.
    • Assess demand before expansion. Avoid entering highly competitive markets without securing customers first.
    • Leverage existing strengths. If you specialize in dry van freight, consider adding refrigerated units only if customer demand justifies the investment.
    • Avoid rapid over-expansion. Expanding too quickly without proper planning can strain cash flow and operations.

📌 Example: A fleet specializing in regional dry van transport successfully added refrigerated trailers after securing contracts with perishable goods suppliers, ensuring a profitable expansion. Caution: Expanding into new markets without understanding rate volatility and operational costs can lead to profit erosion rather than business growth.

Expanding into Drop-and-Hook Freight

For trucking fleets looking to increase efficiency and reduce driver downtime, expanding into drop-and-hook freight can be a game-changer. This strategy allows drivers to swap loaded and empty trailers without waiting for live loading or unloading, improving productivity and profitability.

Zack Germak of Jagtrux explains their strategy:

“We have drop trailers all over the East Coast and our drivers can go in and leave Central PA, go to Columbus to drop-and-hook, go to Erie to drop-and-hook, and more. If you were an independent guy with one truck and two trailers, that is what puts a lot of time in the trucking industry. Oh, I have to wait and sit at a shipper to get loaded. With drop-and-hook, it alleviates all of that.”

To successfully expand into drop-and-hook, fleets must establish a strong trailer pool strategy—such as a 7:1 trailer-to-truck ratio.A 7:1 trailer-to-truck ratio means that for every one truck, the company has seven trailers strategically positioned across the lanes it operates in. This setup:

  • Reduces wait times for loading and unloading.
  • Increases driver efficiency by maximizing driving hours.
  • Enhances load availability for consistent freight flow.
  • Supports customer needs with pre-positioned trailers.

A higher ratio ensures that shippers and receivers always have trailers available, preventing bottlenecks. Here’s how to expand into drop-and-hook freight:

  1. Build Relationships with Shippers and Warehouses: Before investing in more trailers, identify shippers, distribution centers, and warehouses that support drop-and-hook operations. Look for:
    • High-volume shippers that regularly move freight.
    • Facilities with trailer yards for staging preloaded trailers.
    • Customers willing to sign drop trailer agreements to guarantee trailer pools.

📌 Example: A fleet running between Chicago and Dallas secures agreements with retailers and auto part suppliers to drop empty trailers for preloading. This ensures a steady supply of ready-to-go loads in both directions.

  1. Optimize Trailer Pool Locations: Once agreements are in place, position trailers strategically across your network. Focus on:
    • Major freight hubs (ports, distribution centers, manufacturing plants).
    • Balanced freight lanes where inbound and outbound volumes align.
    • Drop yards or secured parking areas for trailer staging.

📌 Example: A regional carrier running freight in the Midwest and Southeast positions trailers at key cross-dock facilities in Memphis, Atlanta, and Indianapolis to maintain consistent trailer flow.

  1. Maintain Equipment Availability: Expanding into drop-and-hook requires scalable trailer capacity. Consider:
    • Leasing or purchasing additional trailers.
    • Partnering with trailer leasing companies for flexibility.
    • Implementing trailer tracking technology to monitor availability.
  2. Train Drivers for Drop-and-Hook Operations. Drivers must be trained to:
    • Perform thorough trailer inspections before hooking up.
    • Use proper drop-and-hook procedures to prevent damage.
    • Communicate with dispatch to ensure efficient trailer swaps.

Final Thoughts

Managing a trucking fleet requires a combination of strategic planning, financial discipline, operational efficiency, and strong relationships. Whether you’re starting or growing your fleet, implementing these fleet management tips can help navigate challenges and build a sustainable, profitable business.

What strategies have worked for your fleet? Share your insights and experiences to help other trucking professionals succeed!

Need help growing a safety department?

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Our PSM Motor Carrier Program includes:

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  • New driver on-boarding
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  • and more

If you need help or have any questions, contact us at 888.260.9448 or info@cnsprotects.com and we would be glad to help.

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