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Marshall Darr
Co-Founder & CEO at StretchDollar
- InsurTech
- Entrepreneur
- 📍Philadelphia, PA
Marshall Darr is the co-founder and Chief Executive Officer of StretchDollar, a health benefits startup based in San Francisco, California, and Philadelphia, PA.
Before co-founding StretchDollar, Marshall spent the last decade helping to make work better for small businesses, first as Head of Lifecycle Marketing for the payroll service company, Gusto, and more recently as VP of Marketing and Partnerships, for Decent, a health insurance startup he helped launch.
Marshall learned early in his career the challenges that small business owners face, having found a startup in the real estate industry, and he can’t think of a more important focus than making it possible for more small business owners to take care of their people, the mission behind StretchDollar.
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LET'S TALK ABOUT
- Health insurance (and how screwed up access is for small businesses)
- Why health insurance access needs to change
- How and why StretchDollar was started
- FinTech innovates InsurTech
- Fundraising after a bank collapse
- Tips for early stage founders
BOOK NOW FOR your podcast
Marshall Darr
Co-Founder & CEO at StretchDollar
- 📍Philadelphia, PA
- InsurTech
- Entrepreneur
Marshall Darr is the co-founder and Chief Executive Officer of StretchDollar, a health benefits startup based in San Francisco, California, and Philadelphia, PA.
Before co-founding StretchDollar, Marshall spent the last decade helping to make work better for small businesses, first as Head of Lifecycle Marketing for the payroll service company, Gusto, and more recently as VP of Marketing and Partnerships, for Decent, a health insurance startup he helped launch.
Marshall learned early in his career the challenges that small business owners face, having found a startup in the real estate industry, and he can’t think of a more important focus than making it possible for more small business owners to take care of their people, the mission behind StretchDollar.
read more
Â
LET'S TALK ABOUT
- Health insurance (and how screwed up access is for small businesses)
- Why health insurance access needs to change
- How and why StretchDollar was started
- FinTech innovates InsurTech
- Fundraising after a bank collapse
- Tips for early stage founders
As seen on
“StretchDollar’s platform seeks to make it easier for small businesses to set up health insurance plans for their employees. Its platform is set to launch in Pennsylvania, Delaware, Illinois and Colorado on Oct. 1. The startup, which has a second headquarters in San Francisco, is tracking to cover California, North Carolina and Texas by the end of 2023 with plans to be in all 50 states in 2024.”Â
“Insurance is one of those things that always seems unnecessarily complicated. But Marshall Darr wants to make it easier for small businesses to provide insurance for their employees.
Enter StretchDollar, which launched this week in Illinois, Pennsylvania, Delaware and Colorado.”Â
“StretchDollar is the easiest way for small employers to give their employees tax-free funding that their employees can use on health insurance premiums. We’ve noticed that traditional group options don’t always work great with the hyper-small employers. We tried to create a way where they can set their own budget, apply it tax-free, and have all of that money go directly to employee-owned health plan premiums.”
“Stretch Dollar, which is launching this month, ‘is something I’ve been tinkering on the last couple of years,’ Darr said. He said the startup helps small businesses and employees save on health insurance plans. The Stretch Dollar platform lets small businesses give employees tax-free dollars for their health insurance premiums, and then the employees get to choose a health plan on StretchDollar’s platform.”
Timeline
Mar 2023 - Present
StretchDollar
Co-Founder & CEO

Jul 2016 - Oct 2018
Gusto
Head of Lifecycle Marketing

Jun 2015 - Jul 2016
Tradecraft
Entrepreneur in Residence

May 2013 - Jun 2015
Stock & Option Solutions
Sales & Marketing Operations Specialist
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Apr 2012 - Nov 2012
Egnyte
SMB Sales Rep
