StretchDollar is a company that creates budget-friendly, customizable health benefits for small businesses. They make the group health insurance process dramatically simpler, more affordable, and more accessible for every small business in America. To learn more about the StretchDollar, Pulse 2.0 interviewed Marshall Darr, co-founder and CEO.
Marshall Darr’s Background
Before co-founding StretchDollar, Darr spent the past decade trying to help small businesses access quality health insurance that they could afford, first, as Head of Lifecycle Marketing at Gusto, a payroll and benefits company, and more recently as VP of Marketing and Partnerships at Decent, a health insurance startup. Darr said:
“The truth is, I stumbled upon Gusto after my own startup failed to take off. But that experience taught me valuable lessons and opened me up to the world of health insurance, employee benefits, and small businesses.”
Formation Of StretchDollar
How did the idea for StretchDollar come together? Darr shared:
“Well before StretchDollar, I spent the last 8+ years trying to figure out a way to make health insurance work for SMBs. I learned that smaller-sized small businesses have it rough — health benefits are too expensive and too complicated — and no one was making it better.”
“StretchDollar is setting out to fix that. Our fintech tool allows small businesses to give tax-free funds to directly cover the premiums on health insurance policies owned by their employees. (We also help match employees to plans that fit their needs).”
Favorite Memory
What has been your favorite memory working for the company so far? Darr reflected:
“Before raising any money, Ellen Decareau (our Head of Customers and Comms) flew out to Philadelphia to work a booth at an event we had sweet-talked our way into a discounted table.”
“We had frantically made some business cards, our first one-pager, and a tablecloth in the few days preceding it. We spent the whole day with a line out of our booth just talking to founder after founder, who seemed to come alive a bit more when they heard what we were putting together for them.”
“When you’re fundraising in arguably the worst climate of the last decade, that real strong market validation felt like a nourishing meal for someone who had been starving. We closed our round shortly after that day, and we haven’t looked back since!”
Core Products
What are StretchDollar’s core products and features? Darr explained:
“Typically, it takes 60+ hours spread over several weeks for a small business to choose and onboard to a group plan, if they can even afford or qualify for one. (Costs typically run about $1,000 per employee.)”
“StretchDollar upends everything about health benefits for SMBs, making it possible for the first time to access benefits immediately, and control their budget, too.”
“StretchDollar’s core product is focused on reimbursements for health insurance premiums. We use technology to enable this in three ways: 1) to allow employers to create a custom health benefit in under 10 minutes, 2) to facilitate the transfer of funds from the employer to the employee (in a compliant and safe way), and 3) to allow employees to shop and purchase their own health plan.”
Evolution Of StretchDollar’s Technology
How has the company’s technology evolved since launching? Darr noted:
“We just launched a couple of months ago, but we’ve already been pushing our priorities due to the strong, early interest we’ve gotten. Pretty soon, we’ll have a broker portal and features for franchise owners to manage multiple businesses.”
Significant Milestones
What have been some of the company’s most significant milestones? Darr cited:
“April 2023 – Initial formation – StretchDollar was born from a large round of layoffs from our previous company. Four of our five employees were among the 60+ health tech experts who suddenly found themselves out of a job. We decided to bundle up and make a go of it on our own.
July 2023 – Closing our $1.6 million pre-seed round during the midst of one of the toughest fundraising environments without having to dribble AI buzzwords throughout our pitch.
October 2023 – Announcing the pre-seed and our pilot program launch and signing up some initial customers the same day.”
Customer Success Stories
After asking Darr about customer success stories, he highlighted:
“We have about a dozen customers currently lined up to offer health benefits through the StretchDollar platform just one week after our launch. Consistently, we hear the same story from founders – they’re trying to figure out how to help their people. But traditional group benefits are too expensive and time-consuming, and the existing system isn’t built to help small employers at all.”
“These are small employers looking to do right by their people, and we’re thrilled to support them.”
Funding/Revenue
After asking Darr about the company’s funding/revenue information, he revealed:
“We’ll start generating our first revenue on 11/1 when our first customers come on board. Our $2 million pre-seed round gives us about 14 months of runway, but we intend to grow fast enough and early enough to not have to cut too deep into that runway before earning ourselves a seed round.”
Total Addressable Market
What total addressable market (TAM) size is the company pursuing? Darr assessed:
“There are more than 5 million small businesses in the US with under ten employees that really have no good option when it comes to health benefits right now.”
Differentiation From The Competition
What differentiates the company from its competition? Darr affirmed:
“One of the biggest differentiators for StretchDollar is our target market focus. Many traditional health insurance group policies are constructed in a way that prevents smaller-sized small businesses from even receiving a quote.”
“We’re steadfastly focused on how we can both provide small employers access to benefits in a scalable, customizable, and competitive way and consistently improve their employees’ experience when it comes to their healthcare with things through partnerships that can help with medical claims, negotiate medical bills and even offer other lines of health care services.”
Future Company Goals
What are some of the company’s future company goals? Darr pointed out:
“Within 10 years, we’re shooting to have a million small businesses on the platform. We want to make small businesses the best place in the world to work – starting with simple, affordable health benefits.”
Additional Thoughts
Any other topics to discuss? Darr concluded:
“Building StretchDollar is a blast. But one of the most important parts that’s rarely talked about is how important it is to stop working.”
“There’s always going to be more to do and more that could be done better, but you’ll blow up your life (and your business) if you don’t learn the discipline it takes to remember that you’re a human being first.”
“This journey is more like a marathon than a sprint, and it’s way too easy to wear yourself out right from the get-go. So, do yourself a favor and be kind to yourself. Set a good example for your team, too, and make sure they’re not overdoing it either. We’re all in this for the long haul.”
