Help small businesses navigate health insurance with confidence. In this role, you’ll guide new clients through enrollment and renewals, making their first experience with SimplyInsured smooth, clear, and stress-free.
About SimplyInsured
SimplyInsured is dedicated to eliminating fear in health insurance. We help small business owners choose the right coverage for their teams through simple, transparent experiences. With more than 20,000 customers and major partnerships including NetSuite, Toast, and Square, we’re reshaping a complicated industry for the better. Backed by top-tier investors from Y-Combinator, Polaris Partners, Bessemer Venture Partners, New York Life Ventures, and AltaIR Capital, we’re growing fast and building a more accessible future for employer-sponsored health insurance.
Schedule
• Fully remote (U.S. only)
• Standard business hours, Monday through Friday
• Collaboration across onboarding, revenue operations, and support teams
What You’ll Do
• Support new customers through the full onboarding process, from application to successful carrier enrollment.
• Assist customers with annual benefit renewals and any coverage or carrier changes.
• Communicate with customers across phone, text, and email to resolve issues and provide proactive guidance.
• Partner with internal teams to ensure a smooth, high-satisfaction onboarding experience.
• Maintain accurate notes and documentation in Salesforce across all customer interactions.
What You Need
• 1–2 years of experience in customer service or a sales-support role
• Life & Health Insurance License or willingness to obtain within 3 months
• Positive, customer-focused mindset with strong empathy and communication skills
• Ability to manage a fast-paced, high-volume workload
• Familiarity with support ticketing systems and CRM software
• Strong multitasking, written communication, and attention to detail
Benefits
• Base pay: $16/hour (unlicensed) or $17/hour (licensed)
• Generous stock option packages
• “Take what you need” time-off plan
• 100 percent employer-paid Medical, Dental, and Vision
• FSA plan
• 401(k)
• A values-driven culture focused on growth, transparency, and employee success
If you’re energized by helping businesses navigate healthcare and want to make insurance simpler for everyone, this could be the perfect next step.
Happy Hunting,
~Two Chicks…