We’re on a mission to make small businesses the best place in the world to work.

And we’re starting with access to simple, affordable health benefits.
A smiling professional man showing a smiling professional woman something on his phone screen.
Full-body photo of Marshall and Kaiza, the co-founders of Stretchdollar.

Our story.

We love small businesses and have spent the better part of a decade putting in work to make their lives just a little easier. We initially met back in the early days of Gusto (a national payroll provider) before leaving to work at an early stage health insurance company.

Time and time again we’d hear from small employers that it was too difficult to fit into a traditional group plan - either it was too expensive, their employees’ health needs were too diverse or they just didn’t have the numbers to make it work.

That's why we launched StretchDollar - a platform that let’s you easily set a pre-tax monthly budget that your employees can use to offset the cost of plans that they select and they own (with help from our expert brokers of course). It should be easy to help your people and with StretchDollar, it finally is.

- Marshall & Kaiza

Our leadership team.

Marshall Darr
CEO
Kaiza Molina
COO
Ellen Decareau
Head of Marketing
Reef Loretto
Head of Engineering
Dolly Dollar
Head of Stretching
Caroline Hou
Head of Customer Experience
Ashton Watson
Sales
Silvia Piscil
Brokerage Ops
Nicholas Park
Product Manager

Small businesses shouldn’t have to:

  • Spend 100+ hours deciphering insurance options every year
  • Need a degree in insurance jargon to understand the offerings
  • Face the impossible task of finding a one-size-fits-all health plan
  • Be put in the awkward position — between employees & their doctors

Small businesses deserve:

  • Benefits that work, even with just one employee
  • Control over their benefits budget
  • A simple, quick health benefits option
  • Confidence that their team has quality health insurance