Startups

This Philadelphia startup offers a fee-free option for small business health insurance

StretchDollar’s CEO spoke to Founding Philly about creating a platform to let small employers offer more flexibility in healthcare plans.

StretchDollar cofounders Marshall Darr and Kaiza Molina. (Courtesy StretchDollar)

For small businesses, options for providing healthcare are limited, but Philly-founded startup  StretchDollar aims to provide a third choice. 

Small businesses can easily spend hundreds of hours setting up a small group plan, incurring costs of around a thousand dollars per employee each month — and still end up with a plan staff might not appreciate due to high copays, high deductibles, and narrow networks.

Or, small business owners can choose to do nothing. Of the 44% of small US employers that don’t offer health insurance, nearly two-thirds said the reason is it’s too expensive, according to a 2023 survey by the pressure group National Federation of Independent Business.

Enter StretchDollar

The platform aims to provide instant, budget-friendly health benefits for small businesses by enabling employers to offer tax-free funding employees can use to pay for individual market health plans that best suit their personal needs.

Every dollar sent through StretchDollar lands in the employee’s bank account, tax free.

CEO and cofounder Marshall Darr spent the last decade immersed in employee benefits at SaaS HR platforms Gusto and Decent, so he has firsthand experience with the challenges small businesses face. 

That experience inspired him and his former colleagues to launch StretchDollar, aiming to provide a clear starting point for businesses seeking health benefits. In 2023, StretchDollar successfully raised $1.6 million in funding from investors including Precursor Ventures, Elefund, v1vc, Kindergarten Ventures, and Westerly Ventures.

In a major move this month, StretchDollar announced it was eliminating all fees.

Tune in to this episode of Founding Philly to hear Marshall share his journey of founding StretchDollar, the invaluable lessons learned along the way, and how he and his team are transforming the approach to health benefits for small businesses and their employees.

This is a guest post by Founding Philly host Zach Brand. A version of it originally appeared in the podcast's newsletter. It appears here as part of a media partnership between Technical.ly and Founding Philly.

Before you go...

Please consider supporting Technical.ly to keep our independent journalism strong. Unlike most business-focused media outlets, we don’t have a paywall. Instead, we count on your personal and organizational support.

3 ways to support our work:
  • Contribute to the Journalism Fund. Charitable giving ensures our information remains free and accessible for residents to discover workforce programs and entrepreneurship pathways. This includes philanthropic grants and individual tax-deductible donations from readers like you.
  • Use our Preferred Partners. Our directory of vetted providers offers high-quality recommendations for services our readers need, and each referral supports our journalism.
  • Use our services. If you need entrepreneurs and tech leaders to buy your services, are seeking technologists to hire or want more professionals to know about your ecosystem, Technical.ly has the biggest and most engaged audience in the mid-Atlantic. We help companies tell their stories and answer big questions to meet and serve our community.
The journalism fund Preferred partners Our services
Engagement

Join our growing Slack community

Join 5,000 tech professionals and entrepreneurs in our community Slack today!

Trending

SEPTA riders complain of more bus cancellations. Here’s why that’s a good thing for Philly transit.

How an experienced entrepreneur learned ‘every facet of business’ by challenging herself

What a second Trump administration means for local startup ecosystems

Discuss how AI is impacting media (and the election too)

Technically Media