Benefits in the US are broken. We just raised $47 million to fix them.

I’m thrilled to announce that Stride Health has raised a $47 million Series C from Mastercard, Allstate and King River to power our next phase of growth and build a new benefits system for individuals. (This story is about our vision. You can read more about our raise today in Business Insider and Forbes .)

I founded Stride to deliver affordable benefits to people who work independently — like the gig economy workers who delivered our food & groceries to my family during the pandemic, the rideshare drivers who get us from point A to B, the caregivers who watch our children and pets, and the ambitious entrepreneurs chartering their own course — Americans who are on their own when it comes to benefits.?

As a child of 2 self-employed parents and the brother of a freelancing sister, I saw first-hand how stressful, confusing and expensive it was for independent workers to get their own health, dental, vision and life insurance. I witnessed the complexities of estimating their own taxes and managing multiple income streams, and the cost of getting that wrong.

I was also struck by how inhospitable our economic infrastructure is to independent workers; everything about our financial system is oriented towards full-time employees. Want to buy a house? The first thing the bank asks for is your W2. Want to save for retirement? Full time employees have you beat since they can invest more and often receive matched contributions in a 401k.?

America’s broken, antiquated benefits system is over 70 years old?

Benefits haven’t caught up with the way we work today. We have 59 million Americans who work independently & outside of the employer benefits system, and that population is growing at triple the rate of the overall domestic workforce. This was a trend before Covid and was accelerated by the pandemic — 12% of the entire US workforce freelanced for the first time in 2020.

But the benefits system hasn’t budged since World War II. Millions are left out of the system and, for those who are included, employers dictate what benefits they can access. When you switch jobs — or lose your job, like millions did in the wake of the pandemic — everything changes.

We need benefits to evolve as our new reality of work evolves. It’s time to create a benefits system for the 90 million Americans who will work independently by 2028. One that’s not tied to your job and that you can take with you, no matter how or where you work.?

Portable Benefits are the solution

To adapt to the new world of work, we need flexible “Portable Benefits” to create a financial safety net for an increasingly independent labor force. I believe that this new system also requires that benefits are accessible to every kind of worker, whether they be full-time, part-time, independent, or gig.

The Portable Benefits model applies well beyond just the “gig economy” too — it could offer large and small employers greater choice in their current “all-or-nothing” binary benefits system employees and alleviate the friction people feel when changing jobs: imagine a world in which you can change jobs but never have to switch health plans or 401K providers.

Stride’s path to Portable Benefits

We started Stride in 2014 with the goal of fixing the broken benefits system in the U.S. and did so in tandem with the launch of the country’s first truly portable benefit: Affordable Care Act health insurance. We built an easy-to-use health insurance recommendation and enrollment experience designed to simplify the process of finding the right plan based on your specific needs—like the doctors you want to keep, the prescriptions you take and the medical conditions you need to treat.

We made it easy to retrieve all of the financial assistance you deserve and provided year-round support from an award-winning team of licensed professionals to help you understand your benefits and put them to work. We added dental, vision and life insurance offerings to round out the core protection each individual should have to keep themselves and their families safe and healthy.

We then added tools and guidance to help independent workers tackle other things normally handled by an HR department, like estimating your tax withholdings, filing your tax forms, and managing your income streams. We helped independent workers track their business expenses and discover new tax deductions so they weren’t overpaying their taxes, and helped them find ways to save money on everyday expenses like prescriptions and eyewear.?

To-date, we’ve helped 2.7 million people save over $2.8 billion on healthcare and taxes — and we’re just getting started.?

Expanding our ecosystem of Portable Benefits enablers with Mastercard & Allstate partnerships.

We’ve partnered with the largest independent workforces in the world — like Uber, DoorDash, Instacart & Amazon — to make benefits easier for their communities, and now with Mastercard to bring those benefits straight to the places they’re getting paid too.

We’ve partnered with the US Department of Health & Human Services to make accessing government benefits easier — through this work, 44% of gig workers we’ve covered pay less than $1. That’s nearly half of our delivery economy members getting free coverage thanks to a seamlessly integrated public-private sector partnership.

Today we’re also announcing that we’ve partnered with Allstate to bring support for a broader set of benefits, in addition to the 200+ health insurance carriers we work with today. And we’re partnered with benefits administrators like Willis Towers Watson and Aon to bring these same benefits to a rapidly evolving Fortune 1000 that's bringing contractors into their workforces.?

With this latest round of capital we’re going to expand our benefits portfolio, invest in serving even more independent workers, and deepen partnerships with more independent work platforms, benefits providers, and financial services providers. We have a bold, ambitious roadmap spanning the next several years designed to ensure every independent worker has the financial security they deserve.

Have other ideas about Portable Benefits or how to protect America's independent workers?

Leave your thoughts in the comments below or feel free to email me at [email protected]. I'd love to hear from you!

Want to join us in creating financial security for everyone who works for themselves?

I’ve got good news for you: we’re hiring. Like crazy! Check out our jobs at https://www.stridebenefits.com/careers . Don’t see your dream job but you’re feeling inspired by our mission? Drop me a line at [email protected].

Want to partner with us to support your community of workers??

Check out what we can do for businesses like yours at https://www.stridebenefits.com

And a big thank you to those who are believers in Stride & Portable Benefits!

Thank you to my entire team at Stride who work incredibly hard every_single_day to make the lives of our members better. You all are inspirations to me and fire me up. You’re doing the hard building to make our vision for a better world come true.

Welcome to our newest investor Megan Guy at King River who led the Series C investment in Stride and was joined by Mastercard, Allstate, all of our existing investors and some amazing new angels like Jonathan Bush, Bruce Perkins, Chet Burrell, Aneesh Chopra, and Kevin Nazemi. And welcome to Opeyemi Oluwole who is joining our Board of Directors alongside Megan.

Thank you to Rick Yang who led our Seed at NEA, Bryan Roberts & Bob Kocher who led our Series A at Venrock, Carl Byers & Ben Malka who led our Series B at F-Prime Capital and all of our angel investors who have supported us along the way. Thank you to early angel investors Owen Tripp, Kevin Systrom, Brent Franson, Larry Leisure, Sami Inkinen, Jim MacDonald, Rock Health, the Crown Family… and my amazing mom.

And thank you to my friend and Cofounder Matt Butner for hatching this special thing we call Stride together.