
StretchDollar
Founded Year
2023Stage
Seed VC - II | AliveTotal Raised
$9.6MLast Raised
$2M | 1 yr agoMosaic Score The Mosaic Score is an algorithm that measures the overall financial health and market potential of private companies.
-44 points in the past 30 days
About StretchDollar
StretchDollar focuses on providing health benefits solutions for small businesses within the insurance industry. The company offers a platform where small businesses can set a budget and match their employees with personalized health plans, simplifying the process of obtaining small business health insurance. StretchDollar primarily serves the small business sector with its health benefits services. It was founded in 2023 and is based in San Francisco, California.
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StretchDollar's Product Videos
ESPs containing StretchDollar
The ESP matrix leverages data and analyst insight to identify and rank leading companies in a given technology landscape.
The ICHRA platforms market consists of companies that offer software to provide individual coverage health reimbursement arrangement (ICHRA) plans. Most ICHRA platforms facilitate payments between employees (sponsored by their employers) and health insurers. ICHRA platforms typically offer employers online portals to administer ICHRA plans, with many companies also offering complimentary portals f…
StretchDollar named as Challenger among 13 other companies, including Gravie, Sureco, and Thatch.
StretchDollar's Products & Differentiators
Small Business ICHRA
A free to use platform for small businesses to offer their employees tax free funding to cover the cost of health insurance plans they select and own themselves.
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Research containing StretchDollar
Get data-driven expert analysis from the CB Insights Intelligence Unit.
CB Insights Intelligence Analysts have mentioned StretchDollar in 2 CB Insights research briefs, most recently on Oct 16, 2025.

Oct 16, 2025 report
Insurtech 50: The most promising insurtech startups of 2025
Aug 7, 2025 report
State of Insurtech Q2’25 ReportExpert Collections containing StretchDollar
Expert Collections are analyst-curated lists that highlight the companies you need to know in the most important technology spaces.
StretchDollar is included in 5 Expert Collections, including Insurtech.
Insurtech
3,403 items
Companies and startups that use technology to improve core and ancillary insurance operations. Companies in this collection are creating new product architectures, improving underwriting models, accelerating claims and creating a better customer experience
Fintech
9,809 items
Companies and startups in this collection provide technology to streamline, improve, and transform financial services, products, and operations for individuals and businesses.
Digital Health
12,122 items
The digital health collection includes vendors developing software, platforms, sensor & robotic hardware, health data infrastructure, and tech-enabled services in healthcare. The list excludes pureplay pharma/biopharma, sequencing instruments, gene editing, and assistive tech.
Insurtech 50 2025
50 items
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Insurtech 50
50 items
Latest StretchDollar News
Nov 5, 2025
StretchDollar , a health benefits platform built for small businesses and startups, has been named as a 2025 Inc. Power Partner award winner. The annual list honors B2B organizations that support entrepreneurs and small businesses in building stronger, more sustainable companies. Founded in 2023, StretchDollar helps small business owners offer affordable, flexible health benefits without the administrative headache of traditional group insurance. “Offering health benefits shouldn't require you to become an expert in insurance,” said Marshall Darr , co-founder and CEO of StretchDollar. “Our goal is simple—make health benefits easy, affordable, and accessible for small teams so business owners can focus on building great companies instead of managing red tape. Being named an Inc. Power Partner reinforces why we're passionate about simplifying healthcare for America's small employers.” StretchDollar's platform is powered by a new type of benefit called an Individual Coverage Health Reimbursement Arrangement (ICHRA) , introduced by federal rule in 2020. With an ICHRA, business owners set a tax-free monthly allowance for employees, who then choose their own health insurance plan (including vision and dental) that fits their needs and location. Why small businesses choose StretchDollar: Health benefits setup is simple and more affordable Employees have the freedom to choose a plan that fits their needs Personalized shopping support from licensed benefits experts. StretchDollar serves businesses with fewer than 50 employees. They've seen an influx of small employers with remote or multi-state workforces, those facing double-digit rate hikes on group insurance plans and small businesses with under 10 employees (who often don't have many choices). “Small businesses face the steepest challenges when it comes to providing healthcare benefits,” said Darr. “We built StretchDollar so they wouldn't have to choose between affordability and taking care of their people.” The Inc. Power Partner Awards are a trusted benchmark for excellence among B2B companies supporting the entrepreneurial ecosystem. See the full list of honorees at inc.com/power-partner-awards About StretchDollar StretchDollar is on a mission to make small businesses the best place in the world to work, starting by making health benefits simpler and more affordable for small businesses. The company is founded by Gusto and health insurance industry alumni and headquartered in San Francisco, California, and Pittsburgh, Pennsylvania. Learn more at StretchDollar.com or email hello@StretchDollar.com View source version on businesswire.com: https://www.businesswire.com/news/home/20251105712753/en/ “Our goal is simple—make health benefits easy, affordable, and accessible for small teams so business owners can focus on building great companies instead of managing red tape." Contacts Ellen Decareau Head of Marketing & Communications (p) 512-300-3334 Ellen@StretchDollar.com
StretchDollar Frequently Asked Questions (FAQ)
When was StretchDollar founded?
StretchDollar was founded in 2023.
Where is StretchDollar's headquarters?
StretchDollar's headquarters is located at 500 Innes Avenue, San Francisco.
What is StretchDollar's latest funding round?
StretchDollar's latest funding round is Seed VC - II.
How much did StretchDollar raise?
StretchDollar raised a total of $9.6M.
Who are the investors of StretchDollar?
Investors of StretchDollar include Expansion VC, Precursor Ventures, Oscar, Fika Ventures, Springbank and 6 more.
Who are StretchDollar's competitors?
Competitors of StretchDollar include Thatch and 3 more.
What products does StretchDollar offer?
StretchDollar's products include Small Business ICHRA.
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Compare StretchDollar to Competitors

zizzl health specializes in providing Individual Coverage Health Reimbursement Arrangement (ICHRA) solutions within the health insurance sector. The company offers a platform that assists employers in managing health benefits, enabling them to provide customizable health insurance options to their employees without the administrative burden typically associated with traditional plans. zizzl health was formerly known as zizzl. It was founded in 2016 and is based in Milwaukee, Wisconsin.

Zorro is a company that provides solutions within the health benefits industry. The company offers a platform that allows employers to set individual benefits budgets for employees, who can then choose their health benefit bundles. Zorro primarily serves the employer and employee sectors, focusing on a health benefits system. It was founded in 2022 and is based in Beachwood, Ohio.

Take Command Health specializes in health reimbursement arrangements (HRAs) within the financial technology sector. The company provides HRA administration software that enables businesses of various sizes to reimburse employees for health insurance tax-free. Take Command Health's main offerings include QSEHRA administration for small businesses and ICHRA administration for companies of any size, aiming to offer flexible and affordable health benefits. It was founded in 2014 and is based in Richardson, Texas.

Venteur specializes in health insurance solutions with a focus on Individual Coverage Health Reimbursement Arrangements (ICHRA) within the healthcare industry. The company offers platforms that allow employers to provide health benefits to their employees and assist employees in creating health portfolios. Venteur's services integrate with payroll systems, providing options for businesses. Venteur was formerly known as BeneSwyft. It was founded in 2020 and is based in San Francisco, California.

BenefitBay provides a range of ICHRA administration platforms within the health benefits sector. Its offerings include a platform that allows employers to reimburse employees for individual health plans while maintaining tax advantages and tools to support simplified benefits deployment and compliance. Its services are primarily utilized by brokers and their clients in the health benefits industry. It was founded in 2021 and is based in Omaha, Nebraska.

Vitable Health provides primary care and mental health services within the healthcare sector. The company offers a membership model that includes virtual and in-home primary care visits, mental health support, access to prescriptions, and solutions for employers. Vitable Health serves employers, brokers, consultants, third-party administrators, and individuals seeking healthcare. It was founded in 2019 and is based in Woodlyn, Pennsylvania.
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