Help small businesses navigate employee health insurance and eliminate fear from one of life’s most complicated decisions.

About SimplyInsured
SimplyInsured is on a mission to eliminate fear from health insurance. We work with small business owners to simplify employee health coverage through transparency, accessibility, and innovation. Since our start in Y Combinator, we’ve grown to serve more than 20,000 customers and built partnerships with major platforms like Intuit and Square. Backed by leading investors including Polaris Partners, Bessemer Venture Partners, New York Life Ventures, and AltaIR Capital, we’re disrupting an industry that impacts millions of lives.

Schedule

  • Full-time, remote (U.S.-based only)
  • Required shift: Monday–Friday, 10am–6pm MST
  • Base pay: $15/hour

What You’ll Do

  • Guide potential customers through our online health insurance shopping experience and provide quotes for small business health coverage
  • Support existing customers with administrative and billing questions via phone, chat, and email
  • Document interactions in support software while ensuring accurate and timely responses
  • Deliver high-quality service to delight customers and help reduce the fear of navigating insurance
  • Share insights from customer interactions to improve processes and products

What You Need

  • 1–2 years of experience in customer service or sales
  • Comfort working in a high-volume contact center environment
  • Familiarity with support CRM or ticketing tools (Zendesk, Intercom, Salesforce, etc.)
  • Excellent oral and written communication skills
  • Strong multitasking and productivity skills
  • Passion for helping people, particularly around healthcare

Benefits

  • Generous stock option packages
  • Competitive compensation
  • “Take what you need” time off policy
  • 100% coverage for medical, dental, and vision insurance
  • FSA plan
  • 401(k)
  • A values-based, transparent culture that invests in your success

At SimplyInsured, every opinion is respected, diversity is celebrated, and we’re unified in our mission to make health insurance transparent and fear-free.

Happy Hunting,
~Two Chicks…

APPLY HERE