StretchDollar offers a cloud‑based platform that lets small employers provide Individual Coverage Health Reimbursement Arrangements (ICHRA) by setting a pre‑tax allowance and guiding employees to choose their own qualified health plans. The system automates IRS paperwork, provides licensed guide support, and enables brokers to quote, configure, and launch ICHRA programs for clients in minutes, delivering predictable budgeting and personalized coverage.
Funding
$7.8M raised to dateRaised to date based on public sources. This may differ from the amount the company actually raised and is based only on what is publicly available on the internet.

2OOHFounders
Product
Problem
Small businesses often cannot afford traditional group health insurance because of high premiums, mandatory participation thresholds, and lengthy setup times, leaving many employees without coverage or forcing employers to forgo benefits altogether.
Solution
StretchDollar provides a cloud‑based platform that enables small employers to offer Individual Coverage Health Reimbursement Arrangements (ICHRA). Employers set a fixed pre‑tax allowance per employee, and the platform guides employees to select their own qualified health plans, either through marketplace options or private insurers. The system automates IRS‑required paperwork, handles year‑end reporting, and offers licensed guides for employee assistance. Brokers and benefits consultants can quote, configure, and launch ICHRA programs for their clients in minutes, with instant pricing and self‑service onboarding. The result is predictable budgeting for employers, personalized coverage for employees, and streamlined administration for brokers.
Target Audience
Primary customers are small‑business employers (typically under 50 employees) seeking affordable health benefits, and insurance brokers or benefits consultants who sell and administer benefits to these employers.
Features
- Instant quoting tool that delivers customized ICHRA pricing in minutes
- Self‑service onboarding workflow for employers to set pre‑tax allowances and invite employees
- Integrated licensed guide support for employee plan selection and enrollment assistance
- Automated year‑end IRS paperwork and compliance reporting
- No participation minimums, allowing any size workforce to qualify
- Nationwide coverage across all 50 states with a single platform
- Broker‑focused dashboard with referral fee tracking and optional broker‑of‑record retention