The Future Driver Workforce: Driver Retention & Fleet Strategy
What You'll Learn:
- How driver expectations are changing across younger generations
- Why predictability and work-life balance are becoming key retention drivers
- The role of technology in improving the driver experience
- Practical strategies for strengthening recruitment and retention
- How workforce strategy and fleet technology can work together to support long-term growth
In this FleetOwner QuickChat, Cyndi Brandt, VP of Fleet Solutions at Descartes, joins Lindsey Trent, Co-Founder and President of the Next Generation in Trucking Association, to discuss how driver expectations are evolving and what fleets can do to adapt. Together, they explore how technology, workforce development, and operational strategy can help fleets meet changing driver expectations.
What Today's Drivers Want
One of the biggest misconceptions in the industry is that higher pay alone drives retention. Today's drivers are looking for more than competitive compensation.
Younger generations increasingly value predictable schedules, work-life balance, career development opportunities, and access to technology that helps them do their jobs more effectively. They also expect transparency around how they're paid, how business decisions affect their day-to-day work, and what opportunities exist for growth.
Descartes’ workforce study shows that these priorities extend across the broader supply chain and logistics labor market. When asked which tactics organizations use to retain workers, respondents most often cited on-the-job training and education compensation, followed by higher pay. Working time flexibility and career planning and promotion programs were also among the top tactics used. For fleets, this reinforces the importance of looking beyond compensation alone and building a driver experience that supports growth, predictability, and long-term engagement.
Building a Stronger Driver Pipeline
Creating the next generation of drivers starts well before the hiring process. Community outreach, partnerships with local schools, and engagement with CDL and technical education programs are helping raise awareness of transportation careers among younger audiences. These efforts not only strengthen the talent pipeline but also showcase the technology, innovation, and career opportunities available in modern fleet operations.
Once drivers join an organization, structured onboarding, mentorship programs, and ongoing development opportunities can play a critical role in workforce engagement and driver retention. Younger workers are often looking for employers that invest in their growth, provide meaningful support, and offer clear pathways for advancement.
Technology As a Driver Retention Strategy
Technology has become an important part of creating a driver-friendly operating model. Route optimization, real-time visibility, proof of delivery, and mobile workflows help reduce friction throughout the day while creating greater transparency and predictability for drivers.
For younger drivers in particular, technology is often viewed as an enabler of success, helping them stay informed, work more efficiently, and focus on delivering exceptional service. When combined with strong workforce strategies, these tools help fleets create a more consistent driver experience while supporting both operational performance and driver satisfaction.
Watch the Recording
As younger generations reshape the transportation workforce, fleets have an opportunity to rethink how they attract, support, and retain drivers. Organizations that combine modern technology with a people-first workforce strategy can strengthen driver retention, enhance operational performance, and better adapt to changing workforce expectations.
About The Next Generation in Trucking Association
The Next Generation in Trucking Association is a nonprofit organization focused on attracting and developing the next generation of trucking and supply chain professionals. Founded in 2021, Next Gen works with schools, students, and industry leaders to promote trucking careers, support training programs, and connect future talent with employers. Its mission is to help build a skilled, diverse workforce while raising awareness of the many career opportunities available across the transportation and logistics industry.
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