---
title: 'Customer Support Representative at SimplyInsured'
canonical: 'https://feeny.ai/job/customer-support-representative-simplyinsured-remote-rt4986w22s5h'
type: 'job'
last_seen: '2026-09-12'
---

# Customer Support Representative at SimplyInsured

- **Company:** SimplyInsured
- **Location:** Remote
- **Work type:** remote
- **Posted:** 2026-09-09
- **Last confirmed live:** 2026-09-12
- **Apply:** https://job-boards.greenhouse.io/si/jobs/8189451

## Job description

At SimplyInsured we are on a mission to eliminate fear in health insurance.

Health insurance is complicated, expensive, and really important - so it tends to create fear for most people; our goal is to reduce that fear as much as possible.

We specifically work with small business owners who have the enormous task of purchasing the right type of insurance for their employees and their families. With more than 20,000 customers and several major partnerships, including NetSuite, Toast ,and Square, we're growing quickly and disrupting this convoluted and confusing industry by making it more transparent and fully accessible to everyone. We got our start in the Y-Combinator incubator, and have been funded by top-tier investors at Polaris Partners, Bessemer Venture Partners, New York Life Ventures and AltaIR Capital.

Job Summary:

In this role, you will be a member of a high-performing team providing service for SimplyInsured customers. This role will help our customers via chat, phone, and email and serve as a trusted representative of the SimplyInsured brand carrying out the mission of eliminating fear from health insurance.

Must be available to work 8:30am -5pm CST Monday-Friday.

What you’ll do:

- Assist potential customers with navigating our online insurance shopping experience and obtaining quotes for their company’s health insurance options.
- Work with existing customers to answer and resolve basic administrative and billing questions. Your main goal will be to ensure that customer inquiries are responded to quickly and thoroughly. You will contribute daily to the Support team’s mission to delight our customers and help eliminate the fear of purchasing and using health insurance.
- In this role, you'll use multiple communication channels, including phone, chat, and email, to communicate with customers and our support ticketing software to document customer interactions. You should be passionate about helping customers and love working in a start-up environment. Being on our customer service team’s front lines means you'll have unique insight and access to our customers' issues. You will be empowered to propose process and product solutions to improve our customer experience.

What you’ll bring:

- 1-2 years of experience in customer service or sales role
- Highly productive with good multitasking skills
- Passion for helping people - especially when it comes to their health
- Able to work in a high-volume contact center environment
- Familiarity working with support ticketing and/or support CRM software tools
- Fantastic oral and written communication skills
- Strong desire to help small businesses and their employees navigate health insurance questions

What we offer:

- “Take what you need” time off plan
- 100% Medical, Dental, and Vision Insurance coverage options for employee and dependents
- Fully Remote
- A values-based culture that invests in employee success

Compensation:

The base salary range for this position is $15.00 per hour

Our Culture:

We value radical transparency, feedback, bias to action, growth, and an obligation to dissent. Every opinion is respected, we hold each other to extremely high standards, we're driven by the diversity in our backgrounds, and unified by 100% alignment on our mission. Research shows that candidates from underrepresented backgrounds often don't apply for roles if they don't meet all the criteria. We strongly encourage you to apply if you're interested; we'd love to learn how you can amplify our team with your unique experience!

We are an equal-opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

#LI-Remote

**SimplyInsured is hiring only in the United States at this time**

## About SimplyInsured

## Company Overview
- **One-liner**: SimplyInsured provides a 100% online platform for small businesses to compare, purchase, and manage health insurance plans from major carriers, eliminating the fear and complexity of healthcare purchasing.
- **Entity Type**: Private (venture-backed)
- **Headquarters**: San Francisco, California, USA
- **Founded**: 2012
- **Founders**: Not publicly available from provided sources

## Core Business
- **Primary industry/industries**: Health insurance brokerage, health insurance technology (Insurtech), small business services.
- **Target customers**: Small businesses (B2B) seeking health, dental, and vision insurance for their employees.
- **Mission or purpose statement**: “Eliminate the fear from purchasing and navigating health insurance in the United States.” [get.simplyinsured.com/about-us](https://get.simplyinsured.com/about-us)

## Products & Services
- **Online Health Insurance Marketplace (SaaS platform)**: A web-based platform that lets small business owners and their employees browse hundreds of plans from major carriers, get instant quotes, enroll entirely online, and manage renewals. Includes payroll integrations with QuickBooks, Square Payroll, ADP, and Paychex. [simplyinsured.com](https://www.simplyinsured.com/)
- **Dedicated Customer Support**: A full-time team of licensed insurance agents provides ongoing support for claims, plan questions, and issue resolution—serving as the business’s own broker.

## Market Standing
- **Valuation/Market Cap**: Not publicly available (private company).
- **Key Metric**: Total funding raised from top investors (amount undisclosed) | 25,000+ small business customers | $10M+ in total savings for those businesses | 90+ employees. [get.simplyinsured.com/about-us](https://get.simplyinsured.com/about-us)
- **Notable Investors/Partners**: Bessemer Venture Partners, Polaris Ventures, Y-Combinator. [get.simplyinsured.com/about-us](https://get.simplyinsured.com/about-us)
- **Growth Signals**: Actively hiring across multiple departments (Engineering, Business Development, Customer Support, Operations) [boards.greenhouse.io/si](https://boards.greenhouse.io/si); remote work model; mission to reach one million small businesses; strong values-driven culture that emphasizes data-based decision making and bias to action.

## Competitive Advantages
- **Full transparency**: Radical openness about salaries, bonuses, equity, fundraising, and even internal Slack conversations/emails, eliminating office politics. [get.simplyinsured.com/careers](https://get.simplyinsured.com/careers)
- **Data-driven decisions**: Every major decision is backed by data, not hierarchy or internal politics.
- **Built-in feedback culture**: Frequent, direct feedback is encouraged and seen as essential to professional growth.
- **Obligation to dissent**: Employees are expected to challenge decisions they disagree with, preventing groupthink.
- **Integrated payroll automation**: Seamless connection with major payroll platforms for automatic deductions and contribution management.

## Strategic Focus
- **Scale to one million small businesses** by continuing to improve the online platform, expand carrier partnerships, and automate more of the insurance lifecycle.
- **Deepen customer support** through a combination of technology and licensed agent expertise.
- **Maintain a culture of radical transparency and data-driven growth** as the company scales.

## Why Work Here
- **Culture**: Unique, values-based environment with radical transparency (everything shared openly), obligation to dissent, feedback culture, and bias to action. [get.simplyinsured.com/careers](https://get.simplyinsured.com/careers)
- **Remote/Hybrid/Office**: Remote work opportunity available; casual work environment with flexible schedules. [boards.greenhouse.io/si](https://boards.greenhouse.io/si)
- **Perks and benefits**: 100% employer-paid medical, dental, and vision coverage for employees and dependents (Built In); competitive salaries; stock options; unlimited vacation; company events; great tech equipment; fun annual work anniversary perks. [builtin.com](https://builtin.com/company/simplyinsured/faq/compensation-benefits)
- **Engineering culture**: Small but impactful engineering team (10 product + tech employees) with direct influence on a $20B industry; data-driven and transparent.

## Sources
1. [SimplyInsured Careers Page](https://get.simplyinsured.com/careers)
2. [SimplyInsured About Us](https://get.simplyinsured.com/about-us)
3. [SimplyInsured Home Page](https://www.simplyinsured.com/)
4. [SimplyInsured Jobs on Greenhouse](https://boards.greenhouse.io/si)
5. [SimplyInsured Compensation & Benefits on Built In](https://builtin.com/company/simplyinsured/faq/compensation-benefits)

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