Affordable, Simple Health benefits. Really.

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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Access Oscar Health with StretchDollar

Your employees* can pick from top health insurance options, including Oscar Health, through StretchDollar.

Oscar Health, founded in 2012, is all about making health insurance simple and supportive—like having a doctor in the family! Our plans are designed for real life with features such as:
A responsive and dedicated care team
24/7 virtual urgent care and prescriptions starting at just $3**
A top-rated mobile app that makes everything easy
*Oscar is available in 18 states
**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 do I get started?

Setting up your benefits plan is quick and easy! Just fill out this form, add a few business details, and choose the pre-tax benefit amount you want to offer your team. That’s it! Have questions? No problem—book a meeting with a StretchDollar + Oscar expert.

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.

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