StretchDollar

StretchDollar operates a benefits platform built around the Individual Coverage Health Reimbursement Arrangement (ICHRA), a structure under which an employer sets a fixed, pre-tax monthly allowance and employees buy their own individual health insurance plans and are reimbursed for premiums. The platform targets employers with fewer than 50 employees and the insurance brokers who serve them, positioning itself as an alternative to traditional group health plans that require carrier negotiations, participation minimums and annual renewals.

The product is delivered as three linked experiences: a broker portal for quoting, client onboarding and enrollment tracking; an employer admin dashboard for setting budgets by employment group, inviting employees, approving premium reimbursements and handling IRS year-end reporting; and an employee benefits portal for shopping on- and off-marketplace ACA-compliant plans, submitting proof of coverage and receiving monthly reimbursements. Employers can configure up to four distinct employee groups with different allowances, enable family scaling for dependents, set waiting periods for new hires and choose any start date during the year. Licensed benefit advisors provide guided plan shopping for employees, and reimbursements are paid by direct ACH transfer to employee bank accounts rather than through debit cards or payroll deduction. The company states employees see 30+ ACA-compliant options on average from national and local carriers, that employer setup takes roughly 10 minutes, and that subsidies are surfaced for qualifying employees [0][3][5].

Founding story

Co-founders Marshall Darr and Kaiza Molina met while working with small businesses at Gusto, where they repeatedly heard owners say they wanted to offer health benefits but could not make traditional group insurance work because of cost, small team size or divergent employee coverage needs. After working in payroll, benefits and health insurance, they built StretchDollar to give employers budget control while letting employees choose their own coverage [2][7].

Business model

StretchDollar sells subscription software and administration services for ICHRA benefit programs. Its published pricing for small-business clients is $100 per month in platform cost plus $25 per employee per month, with no setup fee and cancellation at any time without fees. Brokers who bring clients receive PEPM compensation and can retain agent-of-record status [0][3].

Recurring platform fees charged to employer clients ($100/month plus $25 PEPM), with revenue sharing to brokers in the form of PEPM plus retained agent-of-record commissions [0].

Traction

Named to Inc.'s 2025 Power Partner Awards, which recognizes B2B companies serving entrepreneurs and small businesses. Published customer references include Pawsitively, Zoocade, Righteous HR, TNT Growth and a producer at Gallagher. The about page lists roughly 14 named team members across engineering, brokerage operations, sales, marketing and customer experience [0][2][5][7].

Latest developments

In November 2025 the company published that it had been named to Inc.'s 2025 Power Partner Awards. Its current site emphasizes a broker-first ICHRA platform with a dedicated broker portal, published pricing, a Gallagher + StretchDollar page, 2026 open-enrollment help content, and a new medical bill advocacy perk delivered with Granted [0][2][4][5].