Hassle-Free Health Benefits for Small Businesses

Oscar Insurance and StretchDollar have teamed up to simplify health benefits. You set a budget. We match your employees with plans they want. It’s really that easy.
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Health benefits in a snap for $0.

Give employees pre-tax dollars for health plans they choose — and manage it effortlessly on our free platform. It’s as simple as:
Set your budget.
Decide your team’s monthly pre-tax allowance.
Invite your team.
Employees shop for their perfect plan with access to Oscar’s full suite of easy, affordable solutions.
They get $$$.
You’re done! We’ll take it from here, and get your team set up.
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What others have to say.

Hear from some of our small business customers.

“StretchDollar has made offering health benefits to my team almost effortless.”

Emily de Ayora, President, Design League Co
(5 employees)
Headshot of Emily de Ayora, President of Design League Co.

“If everything was as straightforward as StretchDollar, I’d get a lot more sh** done.”

(Very busy) owner, PlumbSmart, Florida franchise
(10 employees)
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About Oscar Insurance for Employers

Hi, we're Oscar. Our mission is to make healthy living affordable and accessible for all. We started in 2012 to create the kind of health insurance we’d want—one that feels like having a doctor in the family. Over the years, our members have come to love us.
Here’s why:
Highly responsive, dedicated care team to help with any and all questions
Great plan features like 24/7 virtual urgent care and $3 medications*
Top rated mobile app to find care, access these features, and more!
Oscar is available in 18 states--AZ, FL, GA, IL, IA, KS, MI, MO, NE, NY, NJ, NC, OH, OK, PA, TN, TX, VA. On average, employees will find over 9 different insurance companies per state with dozens of insurance plans available to choose from. [Source: KFF.org 2025]

*For full details, visit the Oscar website
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What does it cost to set up? Nothing.

Create your benefits plan for $0. Feel good knowing every dollar goes to your employees - tax free.
Pricing
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Questions?
We've got answers!

How much does it cost?

StretchDollar’s platform is free! Your only cost is the amount you give employees.

What health plans will my employees be able to choose from?

On average, employees will have access to over 9 different national and local health insurance companies (like Oscar Insurance!) offering dozens of insurance plans on the health insurance marketplace. [Source: KFF.org 2025]

How many employees need to enroll?

There is no minimum participation. Even if just one employee accepts the benefit, that’s ok!

How come I’ve never heard of offering health benefits this way?

StretchDollar uses a new benefit model called an ICHRA, made possible by federal legislation in 2020. Adoption has been slow mostly because most ICHRA plans focus on customization for large teams. StretchDollar designed its plans with small businesses in mind -- simplify everything and make health benefits possible in an instant.

Stretchdollar's mascot, Dolly, with two question marks above its head.