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Trucking fleet

Build your trucking community using the top fleet recruitment and retention strategies

March 5, 2024

In the trucking industry today, fleet managers are finding it harder to recruit and retain qualified drivers. Driver burnout, inefficient delivery processes, and the truck driver shortage, are just the tip of the iceberg. 

While no catch-all solutions exist, there are numerous strategies fleet managers can employ to attract and retain qualified drivers to keep business on track during a challenging time where the American Trucker Association estimates a shortfall of 80,000 drivers nationwide.

“It’s one thing when you have a supply chain issue and can’t get stuff onto a truck to get to places,” said Noel Glasgow, Vice President of Sales for WEX’s over-the-road business. “It’s going to be worse when you don’t have drivers to get loads to their destinations.”

2024 brings a fresh set of challenges amidst ongoing supply chain disruptions since the pandemic

In 2021, global supply chains faced unprecedented disruptions due to the Covid-19 pandemic, causing widespread shortages and delays across all industries. As the world continues to recover, 2024 is bringing a new wave of challenges including cybersecurity threats, pressure to increase sustainability and ethical practices, ongoing geopolitical tensions, fluctuations in consumer demand, and the unpredictability that comes with emerging technologies like artificial intelligence (AI) and automation. Navigating these complex issues means businesses need to be innovative in their strategies, and increase collaboration to ensure an efficient flow of goods and services in these tricky times. 

Disrupted supply chains can exacerbate issues like idle times and delays. Each minute a truck remains stationary represents wasted fuel, maintenance expenses, and labor costs which impact the customer, driver, and the company they work for.

“That’s money out of their pocket because it’s a timing-challenged issue for them,” said Matt Crumpton, Vice President of National Account Sales for WEX’s over-the-road business. “As trucks are sitting in line, it is costing either them or the company directly.”

Companies focused on last-mile deliveries, Amazon, for example, offer appealing benefits to drivers given their consistent, close-to-home schedules. This means shorter trips, more time at home, and a better work-life balance. In addition, paying employees with a pay card that offers real-time payments is part of an attractive compensation solution.

Driver support and empowerment builds loyalty and engagement

Dallas, Texas-based Stevens Transport, a leader in refrigerated transportation, is focused on improving their 2,600 driver’s (900 independent contractors) work-life balance, utilizing different capacity programs, regional zones, comfort zones, and more. Good drivers are integral to the company, and the overall supply chain.

“We’re creating a variety of opportunities that fit a lot of drivers,” Vice President of Driver Relations and Administration Angela Horowitz said. “If you’ve got a professional driver, then we’ve got to find a way to support them and their work-life balance.”

Many companies are moving away from outsourcing recruiting in favor of in-house recruitment and retention managers. They provide an authentic listening ear for drivers on a daily basis, providing them with a dedicated support system to solve any issues, making them feel valued and heard in the workplace.

With a constantly changing labor force and landscape, re-education is critical. Stevens Transport offers driver and manager education with the understanding that drivers are “the customer in the front of the truck.” All employees onboarding at Stevens Transport take a driver education course that outlines the value of drivers to Stevens and the expectations Stevens has of their drivers. Horowitz said it’s about having a “partnership” across the organization, from drivers to executive management.

Customarily held in mid-September, some companies recognize a single driver appreciation week isn’t enough. They’ve expanded to monthly or quarterly events.

Stevens Transport’s monthly awards recognize employees, contractors, trainers, and more, often with a monetary bonus. They also offer a variety of rolling driver recognition programs, including Transition Trucking: Driving for Excellence, which inspires the hiring of more veterans, national guard members, and reservists into the trucking industry. Qualified employees are entered to win a fully-loaded Kenworth T680 truck.

“Instead of having just one consistent program for all, we have many enhancement programs that we recently adopted and I’ve seen out in the marketplace,” Horowitz said. “It’s really based on real-time performance, so that their pay comes in real-time and that they have the ability to accelerate their pay for the actual amounts of driving now if they hit different benchmarks.”

Money and benefits incentivize fleet driver loyalty and retention

Some carriers have raised their wages to recruit and retain qualified drivers. Now, in 2024, more and more owners are recognizing just how valuable good drivers are. While technology rules across many industries, the real world doesn’t play by the same rules. Trucking is not something you can automate – humans are indispensable on the road. Retaining responsible drivers is crucial to many trucking companies, therefore, pay raises, bonuses, and other incentives are seeing a rise in the last few years. Companies are doing all they can to attract and retain the top talent.  

Some companies, like Stevens Transport, pay drivers regular wages during the training period. Once paid in increments, many companies dole out signing bonuses in full upfront despite the risk of drivers leaving for the next place offering a signing bonus.

From a retention standpoint, their guaranteed pay program helps them reduce driver attrition. Stevens Transport focuses its recruiting efforts on developing entry-level drivers and offers guaranteed pay to begin at training.

“Most people come from a world where they have some type of fixed income they can count on, so having it be variable based on their or their company’s performance can make it challenging to budget for family needs,” Horowitz said. “Introducing a guaranteed pay program has helped.”

One creative solution for recruitment comes from Ostego, Minnesota-based company, Long Haul Trucking. They repurpose signing bonus dollars to use instead for referral bonuses for drivers who help bring new colleagues aboard.

“Between the equipment we have and the drivers we have, they’re our best recruiting, by far,” Long Haul Trucking CEO Jason Michels said. “There’s no better recruiter than a happy driver.”

Reduce driver attrition by fostering a retention-focused culture 

Long Haul Trucking’s retention strategies go far beyond recognizing top drivers. In fact, Michels said, Long Haul Trucking maintains a steady focus on retention across their management and operations teams. It’s an everyday type of thing.

“Anyone that has contact with drivers has to treat every contact as a retention opportunity,” Michels said. “I think that’s one of the reasons that we do so well, it’s not just one person’s responsibility to retain drivers, it’s everybody’s.”

Long Haul Trucking expects its approximately 350 drivers (approximately half are contractors), which include employees and owner-operators, to participate in quarterly reviews focused on safety and revenue performance. There’s no micromanaging. Autonomy is encouraged.

“If they’re doing a good job we’re leaving them alone, supporting them when they need support,” Michels said. “The balance we’re constantly looking at is how we can make sure to draw attention to positive things without making it feel like everybody gets a trophy.”

Build a brand that speaks to drivers: Craft marketing content that helps build a community within your company

Stevens Transport hosts Stevens Roadside Radio, a regular podcast featuring guests from around their company. It spotlights employees from all parts of the business, including employees and contract drivers. The podcast touches on tips for success, industry news, and stories from across all departments and is shared on company social media. The company is focused on growing its social media presence, hoping to capture every driver or company milestone and success story.

“Trying to build a community is important for driver retention and driver recruitment,” Horowitz said. “We think it’s really important to promote all of the great things about drivers on social media… They need to be heroes all the time, as they keep America moving.”

There’s no one size fits all solution for driver recruitment and retention, but there are plenty of ways to make a difference.

To learn more about WEX, a growing and global organization, please visit

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