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Simple small business health insurance. See hundreds of small business plans at once.

Customer Support Representative (Entry-Level)

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SimplyInsured is on a mission to eliminate the fear from purchasing and navigating health insurance in the United States. 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 6,000 customers and 2 major partnerships with Intuit and Square, we're growing quickly and disrupting this convoluted and confusing industry by making it more transparent and fully accessible to everyone.

Our leadership are MIT alums that have previously founded companies, worked in VC/private equity investing, and top tier management consulting firms. We got our start at YC, and have been funded by top tier investors at Polaris, Bessemer, and Altair.

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.


You will be a Health Care expert working with customers to trouble shoot insurance issues, answer detailed plan questions, and consult small business owners on which plans are right for their employees and their families. Your main goal is to delight our customers and help eliminate the fear from purchasing and using health insurance. You will have an incredible impact on people's individual lives. We're in the business of making sure people have access to resources to live healthy lives. In this role, you'll be using a myriad of communication tools including phone, chat, and email support.

Being on the front lines of our customer service team means you'll have unique insight and access into our customer's issues and you'll be empowered through access to data analytics tools to seek the truth and propose solutions to improve our customer experience.


* Undergraduate or Graduate degree in any relevant field (STEM, business, psychology)
* 0-2 years of experience in customer support or sales role
* Positive and optimistic personality - you help others see the positive in any situation
* Passion for helping people - especially when it comes to their health
* Problem solving skills to navigate complicated issues
* Work hard - play hard, strong desire to help businesses maximize their health care


* Starting salary for all new Customer Support Representatives at $55,000 with a clearly career progression ladder based on metrics & licensing
* Generous stock option packages
* Lunch and Dinner every day (along with snacks and drinks)
* Offsite retreats every 100 days - we have the ability and drive to iterate quickly and this helps us all stay on the same page and develop new ideas
* 100% Medical, Dental, and Vision Insurance coverage
* A values-based culture that invests in employee success


Unlimited Vacation

Healthy Snacks

Company Meals

Weekly Social Events

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