StretchDollar
Health benefits administration platform for small businesses using ICHRA
Overview
StretchDollar is a health benefits administration platform for small businesses and startups that specializes in Individual Coverage Health Reimbursement Arrangements (ICHRAs). The platform allows employers to set pre-tax monthly health allowances and lets employees select individual health plans from national carriers, without the cost and complexity of traditional group insurance.
The platform is delivered as SaaS and includes employer administration tools, employee plan selection guided by licensed benefits advisors, and supplemental benefits through its StretchPerks add-on. StretchDollar also operates as a licensed insurance broker, matching employees with plans from carriers including Blue Cross Blue Shield, UnitedHealthcare, Oscar, and Centene. Setup for employers takes under ten minutes, with support for up to four employee groups, family scaling, and customizable waiting periods.
Founded by Marshall Darr (CEO) and Kaiza Molina (COO) -- former Gusto colleagues -- StretchDollar has raised USD 7.82M across a pre-seed and seed round and was on track to serve over 200 small businesses by end of 2024. The company was named a 2025 Inc. Power Partner award winner and counts insurance brokerage firms Gallagher, NFP, and Lockton among its distribution partners.
Products & Services
ICHRA Platform
A self-service employer benefits administration tool that enables small businesses to establish and manage an ICHRA in under ten minutes. Employers define a monthly pre-tax allowance; employees access a marketplace of 30+ individual health plans available in their area.
Key Features
- Supports all 50 states
- Up to four distinct employee groups per policy
- Family scaling and waiting period customization
- Employee access to licensed benefits guides for plan selection
- Pre-tax employer contributions via business bank account
Target Users: Small business owners and their employees
StretchPerks
An add-on benefits bundle providing access to GLP-1 medications (via Kongo), dental and vision insurance, and medical bill negotiation (via Granted Health).
Key Features
- GLP-1 medication access
- Dental and vision coverage options
- Medical bill advocacy and negotiation
Target Users: Employees enrolled in StretchDollar ICHRA plans
Budget Calculator
A self-service tool on the company website allowing employers to estimate their health benefit costs by state before committing to the platform.
Key Features
- State-based cost estimation
- No account required
- Helps small businesses plan benefit budgets
Target Users: Small business owners evaluating health benefit options
At a Glance
- Founded
- 2023
- Headquarters
- San Francisco, CA
- Employees
- 11-50
- Funding
- Seed
Category & Focus
- Category
- Distribution & Sales
- Subcategories
- Benefits Administration ICHRA Employee Benefits Platform
- Insurance Verticals
- Health Group Benefits
- Target Customers
- Employers, Consumers
Customers
- Righteous HR
- Zoocade
- Pawsitively
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Last updated: 2026-06-23