Help small business owners navigate health insurance with confidence while joining a fast-growing, mission-driven startup.
About SimplyInsured
SimplyInsured is transforming small-business health insurance by eliminating confusion, fear, and unnecessary complexity. Backed by top-tier investors and trusted by more than 20,000 customers, we provide transparent, modern tools that help employers choose the right coverage for their teams. Our culture values radical transparency, action, and meaningful impact.
Schedule
• Fully remote role (U.S. only; some state restrictions apply)
• Standard weekday schedule
• Requires reliable internet and the ability to work across phone, email, and text channels
• Must obtain a Life & Health Insurance License within 3 months if not already licensed
What You’ll Do
• Support new customers through the full onboarding process from application to enrollment
• Assist with annual benefits renewals and carrier or coverage updates
• Communicate with customers via phone, text, and email to resolve onboarding issues
• Partner with revenue operations and support teams for a seamless client experience
• Maintain accurate notes and account details in Salesforce
What You Need
• 1–2 years in customer service, onboarding, or sales
• Life & Health Insurance License, or willingness to obtain shortly after hire
• Excellent written and verbal communication skills
• High-volume multitasking ability across multiple channels
• Strong customer empathy and a positive, solutions-focused mindset
• Experience with support platforms or CRM tools (Salesforce preferred)
Benefits
• Competitive hourly compensation ($16/hr unlicensed, $17/hr licensed)
• Generous stock options
• “Take what you need” PTO plan
• 100% employer-paid Medical, Dental, and Vision
• FSA plan
• 401(k)
• Supportive, values-driven startup culture
If you want to help businesses understand their healthcare options and thrive in a fast-paced, mission-centered environment, this role is a strong fit.
Happy Hunting,
~Two Chicks…