Customer Support Representative (Multi Channel)

About SimplyInsured: Born in Y-Combinator and backed by top-tier investors like Bessemer Venture Partners, SimplyInsured is on a mission to eliminate the fear around health insurance. We empower small business owners by making the task of providing health insurance transparent, accessible, and dead-simple for over 20,000 customers.

The Role

As a Customer Support Representative, you are on the front lines of our mission. This is a multi-channel role spanning Phone, Chat, and Email support where your empathy, speed, and problem-solving skills will directly impact customer loyalty and help turn stressful insurance questions into seamless resolutions.

How You'll Make an Impact

• Be a Trusted Guide: Help small business owners navigate our online shopping platform to find the perfect health insurance quotes for their teams.
• Solve Real Problems: Handle and resolve administrative, onboarding, and billing inquiries with clarity and absolute urgency.
• Master the Stack: Use industry-leading ticketing systems and CRM architectures to cleanly document customer interactions.
• Advocate for Change: Propose product adjustments and internal process updates directly to leadership based on direct client feedback.

What You'll Bring

• 1+ years of high-volume call center experience working inside a remote, fast-paced startup environment.
• Communication: Exceptional oral and written English skills with the ability to distill complex insurance jargon into easy-to-understand explanations.
• Tech-Savvy: Experience navigating modern support tools (such as Zendesk, Freshdesk, or Salesforce) across multiple active workflows.
• Reliability: Must be able to work a consistent schedule of 8:30 am – 5:00 pm CST, Monday through Friday.
• Must be located within the United States.

What We Offer

• 100% Company-Paid Benefits: Complete Medical, Dental, and Vision coverage for you and your dependents.
• Flexible Remote Setup: Work from anywhere inside the United States.
• Generous Time Off: "Take what you need" vacation policy to ensure you stay refreshed.
• A values-driven growth environment where individual viewpoints are deeply valued.