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Customer Support Representative

SimplyInsured

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What representative roles keep asking for: Salesforce (21%), CRM (16%) — counted across their open postings here.

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Preparing for this interview

Interviews for representative roles keep coming back to Salesforce, CRM. Practise those questions before you sit with SimplyInsured.

Questions you are likely to be asked

  1. Why do you want to join SimplyInsured?
  2. What is your experience with CRM? Tell me one thing you learned the hard way.
  3. How do you explain a technical problem to a customer who is not technical?
  4. Tell me about an angry customer you handled. What did you say?
  5. How do you handle a problem you do not know the answer to?

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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:

What you’ll bring:

What we offer:

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**

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Listed on greenhouse · posted 2026-09-09. ApplySarthi collects openings and links to application pages; the role is advertised by SimplyInsured, not by us.