Why Portable Benefits Matter to More than Rideshare and Delivery Drivers
When people hear “gig work” or “independent work” they often think of rideshare drivers and delivery workers. And for good reason — platforms like DoorDash, Shipt, Uber and Lyft have played a major role in the growing shift from traditional W-2 employment to more flexible independent work.
The truth is, rideshare and delivery workers are only a small portion of the total independent worker economy in the U.S. The full breadth of this rapidly growing set of flexible workers is incredibly diverse and includes artists, educators, caregivers, stylists, musicians, healthcare workers, and more.
No matter what slice of the independent workforce they are a part of, these workers face the same challenge – they don’t have the same access to benefits that a typical full-time W-2 worker does.
The Modern Workforce Defies a Single Definition
Today’s workforce is full of people who don’t fit neatly into a traditional 9-to-5. Many work for themselves, hold multiple part-time roles, or move from project to project without the safety net of employer-sponsored benefits. In addition to rideshare and delivery drivers, these workers include:
Freelancers and creatives — from musicians and writers to graphic designers and videographers.
Healthcare professionals — including travel nurses, home health aides, behavioral therapists, contract caregivers, and more.
Retail and small business workers — restaurant staff, hourly retail workers, and part-time boutique employees.
Today’s independent workforce is broader and more dynamic than ever, and it’s time the conversation about access to benefits for these workers reflects that reality.
The Millions of Workers Left Behind by Traditional Benefits
Take Jessica, a freelance graphic designer who turned her passion for lettering and illustration into her career. Or Jeremy, a real estate agent who thrives on the challenges from entrepreneurship. Or recording artist, Ruby Woo whose talents gave her the opportunity to work with major artists like Kendrick Lamar.
Despite their different paths, these independent workers have all faced the same challenge: accessing the benefits that are typically offered to traditional workers, like health insurance, retirement, and paid time-off.
In fact, even popular artists aren’t immune — as pop singer Chappell Roan recently shared from the Grammys stage. During her acceptance speech, Chappell Roan called out the failure of record labels to provide basic support like health insurance for artists. Her words sparked headlines and conversations, revealing just how widespread this issue is in the creative industries.
Very few of these workers have access to employer-sponsored health insurance or a 401(k). But all of them need care when they get sick, income when work slows down, and support for their future.
We need a shift toward a benefits system designed for individuals, not just employees – portable benefits make that possible.
Why Portable Benefits and Why Now
Forward-thinking companies and platforms are beginning to see the value, too. Offering portable benefits isn’t just the right thing to do — it’s a competitive advantage.
Supporting portable benefits can:
Boost recruitment and retention by meeting the real needs of today’s workers
Enhance workforce resilience by reducing financial vulnerability across worker populations
Demonstrate leadership in a changing policy and regulatory environment
Prepare your business for the future of work
With portable benefits legislation progressing, now is the time to act. In February 2025, Representative Kevin Kiley (R-CA) introduced The Modern Worker Security Act, which creates a federal safe harbor that allows companies to contribute to their independent workers’ portable benefits accounts without those workers being reclassified as employees.
In addition to the federal progress, several states are stepping up with new legislation to enable portable benefits. In places like Utah and Tennessee, safe harbor laws now make it easier for organizations to offer contributions to independent workers without triggering reclassification risks. Alabama made history on April 10 as the first state to offer tax-deductible portable benefits contributions, and several other states such as Florida, Georgia, Massachusetts, New Jersey, Ohio, Pennsylvania, and Rhode Island are also exploring portable bills.
How Companies from Various Industries Are Making Portable Benefits Work
Leading organizations across industries are already recognizing that portable benefits are not just a perk — they're a necessity. Here are just a few of the industries that are fueled by independent and traditionally non-benefitted workers:
Portable Benefits for Rideshare and Delivery Drivers
Rideshare and delivery gig platforms helped bring the concept of portable benefits into the national spotlight and they remain one of the largest groups of independent workers in need of support.
In addition to accessing affordable traditional benefits, companies like Lyft, Uber, Shipt, and DoorDash have partnered with Stride to contribute funds into portable benefits savings accounts for their drivers. These dollars can then be allocated to the benefits most relevant to them such as health insurance, child care, emergency savings, or retirement savings. Uber and Lyft are also launching the first-ever joint Portable Health Benefit Fund to administer pooled health insurance stipends to eligible drivers across the state of Massachusetts, powered by Stride.
Portable Benefits for Nurses and Caregivers
Platforms like ShiftKey are empowering travel nurses and healthcare contractors with access to critical protections — recognizing that the people who care for others deserve a system that takes care of them.
Care.com also partners with Stride to provide caregivers access to affordable health plans. In-home caregivers, which include nannies, babysitters, and senior care aides, comprise a significant portion of the overall care workforce, which enables families to work, driving overall economic growth.
Portable Benefits for Musicians and Artists
The Recording Academy — known for championing the rights and welfare of music creators — has partnered with Stride to make benefits more accessible to independent artists and musicians. As artists like Chappell Roan have recently highlighted, even successful performers often lack reliable health insurance. Stride is helping close that gap.
Warner Music Group is also leading the way by partnering with Stride to provide their musicians with access to affordable coverage. Most artists qualify for significant financial assistance under the Affordable Care Act but often don’t realize it. As WMG COO Carianne Marshall said in Billboard, “We’re not only committed to our writers’ careers and songs, but also their well-being.”
Portable Benefits for Retail and Small Business Workers
Companies like Gusto and Homebase are helping small businesses and their employees access benefits that fit today’s flexible work realities. By partnering with Stride, they're making it easier for part-time, hourly, and independent workers to find affordable health coverage and build financial security.
These are just a few examples of what’s possible when companies think beyond traditional models and invest in benefits that workers can actually use — no matter how their work is structured.
The Future of Work — and Benefits — Is Flexible
At Stride, we’re proud to support companies and workers across all industries.
We believe a more inclusive, resilient workforce starts with benefits that move with the worker — and we're excited to continue building that future alongside our partners.