Customer Support Representative (Multi Channel)

Health insurance is complicated, expensive, and intimidating. At SimplyInsured, we are on a mission to eliminate that fear. We empower small business owners—the backbone of the economy—by making the enormous task of providing health insurance transparent, accessible, and dead-simple.

Born in Y-Combinator and backed by top-tier investors like Bessemer Venture Partners, we are disrupting a convoluted industry. We aren’t just a platform; we are a lifeline for over 20,000 customers.

As a Customer Support Representative, you are on the front lines of our mission. You are the voice of calm in a confusing industry. You won't just be "processing tickets"—you will be guiding real people through some of the most important decisions they make for their families and employees.

This is a multi-channel role (Phone, Chat, Email) where your empathy, speed, and problem-solving skills will directly impact our growth and customer loyalty.

• Be a Trusted Guide: Help potential customers navigate our online shopping experience, helping them find the perfect health insurance quotes for their teams.
• Solve Real Problems: Resolve administrative and billing questions with urgency and clarity. Your goal is to turn a "stressful question" into a "seamless resolution."
• Master the Stack: Use industry-leading support tools and CRMs to document interactions and ensure no customer is left behind.
• Advocate for Change: You have a front-row seat to our customers’ challenges. You are empowered to propose product and process improvements directly to our leadership team.
• Deliver "Delight": Maintain high productivity in a fast-paced, high-volume environment while keeping a "people-first" attitude.

• Experience: 1-2 years in a customer-facing role (Support, Retail, or Sales) in a remote, startup environment. 
• Communication: Exceptional oral and written skills. You can explain complex topics in a way that is easy to understand.
• Tech-Savvy: Familiarity with support ticketing systems (like Zendesk, Freshdesk, or Salesforce) and the ability to multitask across several tabs and tools.
• Empathy: A genuine passion for helping people and a desire to support small business owners.
• Reliability: Ability to work a consistent schedule of 8:30 am – 5:00 pm CST, Monday through Friday.

We are driven by the diversity of our backgrounds. Research shows that candidates from underrepresented backgrounds—including women and people of color—often apply only if they meet 100% of the criteria.

At SimplyInsured, we want to change that. If you are passionate about our mission and have a heart for service, we want to hear from you—even if you don't check every single box.

SimplyInsured is an equal opportunity employer. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.