In the ever-evolving world of transportation, one topic is gaining traction among industry professionals, motor carriers, policymakers and independent contractors alike: portable benefits.
Legal and insurance experts Greg Feary (Scopelitis Law Firm) and Chris Gulker (TrueNorth Companies), along with hosts P. Sean Garney and Steve Keppler, explored how portable benefits could impact and reshape the future of trucking.
Short on time? Check out the high-level recap below. But be sure to listen to the full episode so you don’t miss any important insights!
Traditionally, benefits like health insurance, retirement plans and paid leave are tied to employment. But for independent contractors — who make up a significant portion of the trucking workforce — this model doesn’t apply. Portable benefits aim to link benefits to the individual, not the employer. This means contractors can carry their coverages from one job to the next, maintaining continuity and security.
Chris Gulker offered a compelling reframing: “We shouldn’t be talking about benefits in its traditional definition... really more so thinking about portable solutions.” In the trucking industry, where driver misclassification risks loom large, even the word “benefits” can trigger legal scrutiny. Portable “solutions”, like insurance products tailored for independent contractors, offer a compliant way to support drivers without jeopardizing their classification status.
Currently, California, Alabama, Tennessee and Utah have enacted portable benefits laws. California’s Proposition 22, for example, was a direct response to California’s AB5 law and allows gig workers to access certain protections while maintaining independent contractor status.
However, the patchwork nature of state laws raises questions. What happens when a driver crosses state lines? Can benefits truly be “portable” in a fragmented system? As Greg noted, “Until it becomes a universal solution... you're going to have a patchwork quilt of problematic issues.” .
While portable benefits offer promise, they’re not without challenges:
TrueNorth’s TrueChoices program has been offering portable insurance solutions for over two decades. Built on an association chassis, it provides independent contractors access to:
Participation rates vary, but fleets with high engagement see tangible benefits. Chris shared that contractors enrolled in True Choices “turn over at half the rate of the fleet’s general population.”
The trucking industry faces an ongoing capacity and driver shortage, high turnover, and rising healthcare costs as well as just about every other cost element of their P&L. Portable benefits could be a strategic lever to address these issues. Rising litigation and state action on this issue being driven by Prop 22 in California is creating more buzz and attention, resulting in IC’s and motor carriers looking for additional options.
Moreover, with the average commercial driver’s age of death at just 61, access to healthcare could be life changing. Chris wonders, “How much could we prevent if we were to have some type of healthcare program for these drivers that really works?”
To move the needle, industry leaders must engage with legislators and regulators. Greg Feary suggested a “quid pro quo” approach: if carriers are expected to shoulder more costs, they need protection from litigation. Meanwhile, Chris urged the industry to highlight the real-world impact on turnover, health outcomes and driver satisfaction.
Portable benefits aren’t just a policy issue — they’re a people issue. As the gig economy grows and the trucking workforce evolves, solutions like TrueNorth’s TrueChoices offer a path forward. Whether through state legislation or federal action, the goal is clear: empower independent contractors with the tools they need to thrive and offer choices that best fit their needs.
Join The Inside Lane - your fast track to industry insights, fresh episodes and expert perspectives.