# SimplyInsured

> SimplyInsured is an online health insurance marketplace and benefits administration platform built for small businesses. It lets owners shop, compare, and enroll in medical, dental, and vision plans from 200+ carriers in minutes, then automates employee deductions and payroll syncing - all at no cost beyond the regular premiums. The company powers embedded health benefits inside Square, Gusto, Check, and Patriot payroll.

- **Founded:** 2012
- **Headquarters:** San Francisco, California, United States
- **Founders:** Vivek Shah (Co-Founder & CEO), Bob Aspell (Co-Founder)
- **Team size:** 47-90 employees
- **Products:** Health Insurance Marketplace, Benefits Administration Dashboard, Payroll Integrations, Embedded Insurance, Dedicated Broker Support
- **Notable:** Launched out of Y Combinator (2013 batch), Raised $8.5M+ across seed and Series A rounds, Reported 25,000+ small businesses insured

## Products & services

- **Health Insurance Marketplace** — Search, compare, and enroll in medical, dental, and vision plans from 200+ major carriers, with real quotes generated in seconds.
- **Benefits Administration Dashboard** — Manage employees, contributions, deductions, HSAs/FSAs, taxes, and invoices from a single online dashboard with one-click changes.
- **Payroll Integrations** — One-click integrations with major payroll platforms that automatically sync contributions and deductions every pay run.
- **Embedded Insurance** — White-label health benefits embedded inside partner payroll products like Square Payroll, Gusto Embedded, Check, and Patriot.
- **Dedicated Broker Support** — A full-time, licensed support team that works for the customer - not the carrier - handling questions, enrollment, and issues.

## Achievements

- Launched out of Y Combinator (2013 batch)
- Raised $8.5M+ across seed and Series A rounds
- Reported 25,000+ small businesses insured
- Reported $50M+ in total savings generated for small businesses
- Became the embedded health-benefits engine for Square, Gusto, Check, and Patriot payroll

## Latest updates

- **2018-11** — Square Payroll launched benefits offerings with SimplyInsured as its embedded health insurance partner.
- **2015-06** — Closed $5.9M Series A led by Polaris Partners.

## Links

- Website: https://simplyinsured.com
- LinkedIn: http://www.linkedin.com/company/simplyinsured
- Twitter/X: https://twitter.com/SimplyInsured
- Facebook: https://facebook.com/SimplyInsured

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Profile page: https://yespress.io/simplyinsured
Published by YesPress — https://yespress.io
Last updated: 2026-06-08