Everyone deserves affordable health insurance.

This is what keeps us up at night. Health insurance is too expensive, too complicated, and too inaccessible to too many.
Illustration of a hand holding a bouquet

Small businesses want to help.

But the existing options are simply too expensive and too complicated. We’re on a mission to change that. StretchDollar is the simplest, most cost effective way to help your people with their health insurance.

Our story.

StretchDollar was built on a simple premise: small businesses deserve access to simple, affordable health benefits.

Before co-founding StretchDollar, Marshall Darr and Kaiza Molina worked together at two other small business-focused startups. First, in 2016, where they built out Marketing Operations at the payroll company Gusto and then again, four years later, at Decent, a health insurance startup that Marshall helped build from the ground up. The most recent stop is where Marshall and Kaiza developed a deep understanding of the health insurance space and how few options there are for small businesses.

They left to start StretchDollar with the goal of helping those companies that don’t fit the narrow mold that group plans were designed to serve. (Basically, the entire small business community.) Everyone should be able to take care of their people.

Our leadership team.

Kaiza Molina
Marshall Darr
Reef Loretto
Head of Engineering
Ellen Decareau
Head of Customers & Comms
Dolly Dollar
Head of Stretching
Aaron Petramale
Sales & Lifecycle

Our values


At StretchDollar we’ve taken on the horrific burden of deeply understanding each letter in the HRA alphabet soup to make sure that we can explain them all simply enough to avoid tossing you into the acronym abyss.


Great companies are built through consistent, diligent effort applied over a long time. You might think we’re moving quickly when really all you’re seeing is the visible portion of consistent hard work.


Our work shines the brightest when we have fun doing it. How could we expect anyone else to be excited about it if we’re not?


Nothing perfect ever gets done. A bias towards action, with the necessary discipline to ensure that we clean up after ourselves, will help us bring our vision to life.