TN Truck Thought Podcast Episode 33
posted by TrueNorth Transportation on Thursday, September 11, 2025
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Portable Benefits in Trucking: A Game-Changer for Independent Contractors
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!
What are portable benefits?
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.
Why "solutions" might be the better word
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.
The legal landscape: four states and counting
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.” .
Challenges and considerations
While portable benefits offer promise, they’re not without challenges:
- Cost and administration: Not all contractors want or need benefits, and some prefer higher compensation over some benefits and coverage.
- Legal complexity: ERISA laws and misclassification risks require careful program design.
- Adoption rate: Despite growing interest, only a handful of states have passed legislation to date, and federal efforts are still in the early stages.
TrueChoices: A proven model
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:
- Medical, dental and vision insurance
- Life and disability coverage
- Accident and critical illness protection
- Retirement and legal plans
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.”
Why this matters and why now?
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?”
Looking ahead: advocacy and action
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.
Final thoughts
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.
TN Truck Thought
The TN Truck Thought podcast keeps transportation leaders of today and tomorrow in the know on the hottest industry trends. Our specialists get to the bottom of challenging, and sometimes controversial, transportation topics to offer insight and predictions.
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About Author
TrueNorth has a team of dedicated transportation staff with deep specialization to each facet in the industry. Our solutions beyond the insurance policy help transportation companies reduce risk in new, innovative ways. Learn more about the solutions we offer here or call us at (800) 798-4080.
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