Keeping Employees Happy: How Work Truck Fleets Can Improve Employee Retention
Engaging Tech to Boost Driver Recruitment
Tying together driver recruitment, onboarding, and retention efforts in a master technology platform can help fleet carriers overcome many of the challenges brought on by the ongoing driver shortage.

Using technology platforms can help recruit and retain drivers.
Photo: Work Truck
The ongoing driver shortage has been the highest hurdle fleet carriers faced in the last decade — and it’s not going away anytime soon. According to the American Trucking Associations, the driver shortage is expected to surpass 160,000 drivers by 2030.
The government has passed measures such as the Trucking Action Plan, Driving Good Jobs initiative, and Drive Safe Act to help fleet carriers hire drivers quicker, increase training and improve driver engagement and retention.
So far, more than 50,000 commercial driver’s licenses and learner’s permits were issued each month in 2021, 72% higher than the 2020 monthly average, according to the Federal Motor Carrier Safety Administration (FCSM).
Nevertheless, closing the gap on drivers alleviates only one issue. Retention of quality drivers remains a challenge for fleet carriers of all sizes, and compliance challenges complicate matters further.
The FCSM was on track to double the number of off-site audits it performed in 2021. Plus, fines for compliance issues have increased — and in the case of each violation of the Drug and Alcohol Clearinghouse, the fine has jumped to $5,833.
Unfortunately, it is a perfect storm for fleet carriers and other industries that use truck drivers to move materials and goods. Fortunately, innovative technology is stepping up to meet the needs of fleets better and faster.
Happy, Healthy Drivers = Healthy Workforce
Drivers have little time to focus on their health. In fact, 54.2% of truckers suffer from obesity; 47.2% have liver disorders and 32.8% are diabetic, according to Healthy Trucking of America.
To combat this, more of them are now seeking the same health and wellness benefits that white-collar office workers typically get, including:
Mental health care.
Elder care.
Child care.
Gym discounts.
Health savings accounts.
To hire and retain quality drivers in this economy, fleets must offer more attractive benefits to help engagement, and they need to be holistic and driver-centric. The right technology can help tie benefits together and manage any follow-through for drivers — both employees and independent contractors — in any size fleet.
Use technology to turn the downsides of long-haul driving (sedentary time behind the wheel, minimal breaks, etc.) into positives to improve driver health. Behavioral health counseling via phone can help drivers keep their mental health in top shape, even while out on the road.
In addition, apps exist to help drivers with caregiving services and streaming workouts that drivers can do any place, any time, even just for a few minutes at a rest stop.
How it all Plays into Retention
Drivers want to be part of a great fleet. And a carrier’s reputation is built in part around how it treats its drivers.
This starts during the application process and continues through onboarding and beyond. Carriers can make it easier for drivers to apply by streamlining the application process online, digitizing safety training, and making audit/safety inspections trackable on a company portal.
Drivers are more likely to stay with a motor carrier if it offers the following:
Job security.
Safety.
Flexibility.
Choice of routes.
Good income and benefits.
Customized options such as pet insurance.
Carriers who are creative and focused on driver engagement and incentivization have seen success in retention. One carrier printed drivers’ names on the cabs after six months and saw a 40% reduction in accidents.
Make incentives a game-based opportunity for drivers to ramp up engagement and drive results.
Since a driver spends more than 100,000 miles per year on the road, every point of communication is pivotal to job satisfaction.
Honesty and integrity should form the foundation of any driver communication strategy. Technology may help carriers connect with drivers, but expanding engagement opportunities through new, digital tools can help drivers feel even more connected to the fleet.
Prioritizing Driver Needs
It is nearly impossible for fleet carriers to tie together all these recruitment, training, health and wellness, benefits, and other retention strategies without engaging technology to help.
The fleet carrier of 2023 will want to optimize operations while digitizing its onboarding, assessment, orientation, and certification programs to both efficiency, drive down costs, and reduce risks.
About the Authors: Wendy King is the Director of Health and Performance for global employee benefits insurance brokerage Hub International and a leader in the field of healthcare communications and corporate wellness strategy.
Scott Fouts is Vice President of global insurance brokerage Hub International’s Risk Services Division. He has 17 years of experience in occupational safety, health, and risk management consulting. This article was authored and edited according to WT editorial standards and style. Opinions expressed may not reflect that of WT.
More Operations

Family Ties Inside the Fleet Families Building Careers Across Generations
Three fleet families share what it really takes to work together, learn across generations, and keep business from following them home.
Read More →
Shades of Fleet Call for Voices: Fleet's Hidden Heroes
Fleet’s hidden heroes are often the ones keeping everything moving behind the scenes. September’s Shades of Fleet is looking for dispatchers, coordinators, parts specialists, and other support pros to share their stories.
Read More →
Truck Centers, Inc. Celebrates National Truck Driver Appreciation Week with $1,000 Fuel Card Giveaways
During National Truck Driver Appreciation Week, Truck Centers, Inc. is offering customers a chance to fuel up for free. Customers at all Truck Centers locations can enter to win one of four $1,000 fuel cards from Sept. 14 - 18.
Read More →
Fleet Guides, AI Time-Savers, Truck Tariffs & Fuel Strategy Lead the News
This week’s Truck Chat Cheat Sheet covers new fleet vehicle guides, practical AI use cases, U.S.-Canada truck production, mixed-energy strategy, and more.
Read More →
What Fleet Employers Are Missing When Hiring Veterans
What if some of the strongest candidates for fleet are already out there, but their experience is written in a language our industry does not always recognize?
Read More →
Automotive Fleet Opens 2026 Personal Use Survey for Commercial Fleet Managers
Less than two weeks left! Commercial and corporate fleet managers are invited to share how their organizations handle company vehicle personal-use policies, charges, and driver eligibility.
Read More →
What Resilient Fleets Do Differently When Conditions Change
Fleet resilience is about more than reacting to disruption. Lauren Fletcher talks with AP Fleet’s Alex Coveney about flexibility, planning, scaling, and what helps fleets adapt when business conditions shift.
Read More →
If We Want the Next Generation in Automotive, We Have to Give Them a Reason to Care
The automotive industry talks constantly about its workforce shortage. But before we can recruit the next generation, we may need to do a better job giving kids a reason to care about automotive in the first place.
Read More →
Ram ProMaster City Under $40K, Truck Tariffs, and AI Maintenance Lead the News
A sub-$40K commercial van, tariff questions, AI-powered maintenance, and a new EV production strategy headline this week’s Truck Chat Cheat Sheet.
Read More →Bob Adamsky Shares the Fleet Lessons You Usually Learn the Hard Way
After more than 30 years in fleet, Arrow International’s Bob Adamsky has learned that the job is about far more than vehicles. He shares the lessons he wishes every fleet manager could learn a little earlier.
Read More →
