Licensed Medicare Sales Agent

Job Description Job Description Sales Support Specialist – Medicare (Seasonal Temp) Location: Remote | Type: 1099 Seasonal - Full Time (with potential for Permanent) At Healthpilot, we’re transforming the way people shop for Medicare plans—making it simple, personalized, and stress-free. We’re looking for licensed sales professionals who thrive in a service-first environment. This is not a cold-calling role. Instead, you’ll guide customers through their Medicare plan options using our intuitive platform, helping them make confident, informed decisions—and closing the sale when the time is right. What You’ll Do: Deliver a world-class customer experience while driving enrollments through consultative sales. Use your Medicare expertise to educate customers and recommend plans that best meet their needs. Confidently close sales by guiding customers to the right plan and completing the enrollment process. Handle inbound inquiries via phone, chat, SMS, and email—no cold calls. Make outbound follow-up calls when needed to support the customer journey. Maintain a positive, empathetic, and professional tone—even when customers are frustrated. Collaborate with your team to manage high-volume periods and ensure seamless service. Troubleshoot issues with patience and clarity, always keeping the customer’s goals in mind. What You Bring: Active Health Insurance License (Required) 1 year of Medicare experience 3 years of sales experience, with a proven ability to close deals 5 years in customer service or sales support Strong communication skills and a passion for helping others Ability to navigate multiple systems/screens efficiently Comfortable working an 8-hour shift at a desk with scheduled breaks Proficiency with Windows, MS Office, and web-based tools Why Join Us? No cold calling—just meaningful conversations that lead to real impact Be part of a mission-driven team that’s simplifying healthcare for millions

Location: Hartford, Connecticut, US

Posted Date: 8/18/2025