SimplyInsured

SimplyInsured

Online health insurance platform for SMEs

Overview

SimplyInsured helps small and medium-sized businesses provide health coverage to employees. It operates an online platform that lets business owners get instant health insurance quotes and complete applications online in under 10 minutes, with the option to set up automatic premium payments and payroll deductions that sync with major payroll systems. Health plans are purchased through the platform, with SimplyInsured earning commissions from insurance carriers for each policy sold. This aligns its incentives with helping clients find affordable, suitable coverage quickly. The company differentiates itself through its focus on onboarding speed, seamless payroll integration, and strong, personalized customer support that advocates for clients during the enrollment and claims process. The goal is to simplify the health-insurance purchasing experience for SMEs, removing administrative burdens and enabling employees to receive essential coverage efficiently.

YC Company

About SimplyInsured

Simplify's Rating
Why SimplyInsured is rated
C+
Rated C on Competitive Edge
Rated B on Growth Potential
Rated C on Differentiation

Industries

Enterprise Software

Financial Services

Healthcare

Company Size

11-50

Company Stage

Series A

Total Funding

$8.6M

Headquarters

San Francisco, California

Founded

2012

Simplify Jobs

Simplify's Take

What believers are saying

  • Patriot Software integration embeds health shopping directly in payroll software.
  • QuickBooks Payroll partnership expands reach to millions of Intuit-dependent small businesses.
  • Remote partnership positions SimplyInsured as US benefits broker for global payroll clients.

What critics are saying

  • BambooHR and Gusto embed health quoting via carrier APIs, bypassing commission brokers.
  • CMS 2025 ACA transparency rules enable direct carrier sites and HealthSherpa competition.
  • Guideline 401k bundling with QuickBooks erodes SimplyInsured's exclusive payroll integrations.

What makes SimplyInsured unique

  • 100% free platform with instant quotes from all major carriers nationwide.
  • One-click payroll integration with ADP, Paychex, QuickBooks, Square, and Patriot.
  • Licensed benefits broker offering unbiased recommendations across medical, dental, vision.

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Funding

Total Funding

$8.6M

Below

Industry Average

Funded Over

4 Rounds

Series A funding typically happens when a startup has a product and some customers, and now needs funding to scale. This money is usually used to grow the team, expand marketing, and improve the product. Venture capital firms are frequently the main investors here.
Series A Funding Comparison
Below Average

Industry standards

$15M
$5.9M
SimplyInsured
$8.2M
Discord
$15M
Canva
$30M
Kalshi

Benefits

Medical, dental, vision coverage

Stock options

Competitive salaries

Unlimited vacation

Casual work environment

Remote work opportunity

Company events

Flexible work schedule

Great tech equipment

Fun annual work anniversary perks

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

0%

2 year growth

-4%
Patriot Software
Nov 11th, 2025
Patriot Payroll Customers Can Now Add Health Benefits in Just a Few Clicks

Patriot Payroll customers can now add health benefits in just a few clicks. Patriot Software, a leader in cloud-based payroll and accounting solutions, has joined forces with SimplyInsured, a digital benefits platform, to simplify one of the toughest jobs for small business owners: offering health insurance. The new integration embeds insurance shopping, enrollment, and payroll deductions directly inside Patriot's payroll software. For many small businesses, offering healthcare has long been a challenge. Studies show that only about half of small businesses offer employer-sponsored health insurance. For many business owners, the process of comparing plans, managing enrollment, and managing payroll deductions and contributions is confusing and time-consuming. Patriot Payroll(R) now integrates with SimplyInsured, removing previous roadblocks for customers. This integration allows customers to browse plans from leading carriers, receive instant quotes and automatically sync all group benefit information from employee health benefit deductions to employer contributions directly into payroll, eliminating extra steps. "Small business owners wear enough hats already," said Amie Scarpitti, Product Manager. "This integration takes something notoriously complex - health benefits - and makes it simple. Now, Patriot customers can run payroll and offer healthcare in the same place, without extra forms, spreadsheets, or headaches." This new collaboration takes the pain out of managing payroll and health benefits. It's another step in Patriot's mission to make payroll simple for American businesses and give owners back the time to focus on expanding their business and supporting their workforce. Businesses interested in streamlining their payroll and benefits can learn more and schedule a demo at Patriot Software's website. New customers receive a 30-day free trial and 50% off software pricing for the first three months. About Patriot Software Patriot provides cloud-based accounting, payroll, HR, and time and attendance software designed to help American businesses with up to 500 employees cut through administrative work. Known for affordable pricing and award-winning products, Patriot ranks in the 100th percentile for customer loyalty and satisfaction. Its U.S.-based support team delivers a level of personal service rarely found in the software industry. Since 2002, Patriot has served tens of thousands of businesses nationwide. About SimplyInsured SimplyInsured is a digital health insurance platform that enables small businesses to compare and manage employee health benefits. With instant quoting, online enrollment, and streamlined compliance, SimplyInsured empowers business owners to find the right coverage with clarity and confidence.

NerdWallet
May 27th, 2021
247quickbooks partners with SimplyInsured, Inc.

QuickBooks Payroll partners with SimplyInsured and Guideline to offer benefits.

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