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Marshall Darr

Co-Founder & CEO at StretchDollar

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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BOOK NOW FOR your podcast

Marshall Darr

Co-Founder & CEO at StretchDollar

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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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.” 

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“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.” 

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“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.”

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“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.”

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Timeline

Mar 2023 - Present

StretchDollar

Co-Founder & CEO

Mar 2023 - Present

Oct 2018 - Mar 2023

Decent

VP of Sales and Marketing

Oct 2018 - Mar 2023

Jul 2016 - Oct 2018

Gusto

Head of Lifecycle Marketing

Jul 2016 - Oct 2018

Jun 2015 - Jul 2016

Tradecraft

Entrepreneur in Residence

Jun 2015 - Jul 2016

May 2013 - Jun 2015

Stock & Option Solutions

Sales & Marketing Operations Specialist

May 2013 - Jun 2015

Apr 2012 - Nov 2012

Egnyte

SMB Sales Rep

Apr 2012 - Nov 2012

Ask me

Why StretchDollar?
Tell us about yourself & how you started StretchDollar.
Why is it so hard for small employers to access health insurance?
What problem is StretchDollar fixing?
What are the biggest wins you've had as a founder?

Podcast agent: Kate N

kate@kitcaster.com

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