S

SimplyInsured

Online health insurance platform for SMEs

Customer Support Representative

Full-Time
$15/hr
Junior
Remote in USA
Remote

About the job

Requirements
  • One to two years of experience in a customer service or sales role.
  • Ability to work in a high-volume contact center environment.
  • Familiarity with support ticketing and/or support customer relationship management software tools.
  • Availability to work from 8:30 a.m. to 5 p.m. Central Standard Time, Monday through Friday.
Responsibilities
  • Assist potential customers with navigating the online insurance shopping experience and obtaining quotes for their company's health insurance options.
  • Answer and resolve basic administrative and billing questions for existing customers.
  • Respond to customer inquiries quickly and thoroughly through phone, chat, and email.
  • Use support ticketing software to document customer interactions.
  • Propose process and product solutions to improve the customer experience.
Desired Qualifications
  • Highly productive with good multitasking skills.
  • Passion for helping people, especially with health-related matters.
  • Strong oral and written communication skills.
  • Strong desire to help small businesses and their employees navigate health insurance questions.

About the company

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.

Company Size

11-50

Company Stage

Series A

Total Funding

$8.6M

Headquarters

San Francisco, California

Founded

2012

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Simplify's Take

What believers are saying

  • Patriot launched its integration on 2025-11-11, expanding distribution instantly.
  • Company materials claim 25,000 customers and over $50 million in saved premiums.
  • SimplyInsured reports 90-plus employees and $10 million-plus capital raised as of 2026-08-25.

What critics are saying

  • Patriot can replace SimplyInsured with another broker if economics weaken in 2027.
  • Health insurance commissions compress under carrier pressure and broker disintermediation.
  • A compliance mistake with broker-of-record transfers triggers audits, disputes, and customer churn.

What makes SimplyInsured unique

  • SimplyInsured embeds health benefits into Patriot Payroll and other payroll stacks.
  • Its 50-state quoting engine compares 200-plus carriers in one workflow.
  • The platform turns enrollment, deductions, and renewals into a single online process.

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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

↓ -2%

1 year growth

↓ -2%

2 year growth

↓ -6%
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.