Healthpilot Technologies Jobs (NOW HIRING)

Licensed Medicare Sales Agent (Seasonal)

Location: Remote | Type: Seasonal W2

At Healthpilot, we're transforming the way people shop for Medicare — making it simple, personalized, and stress free. During Annual Enrollment Period (AEP), our Licensed Sales Agents are at the heart of that mission: guiding customers through their Medicare plan options, helping them make confident decisions, and closing enrollments with care and expertise.

This is not a cold-calling role. Whether inbound or outbound, every person you speak with has already shown interest — customers come to us ready to explore their options, and your job is to meet them there.

What You'll Do

• Deliver a consultative sales experience that puts the customer's needs first, every time.
• Use your Medicare expertise to educate customers, recommend the right plans based on their needs, and confidently guide them through enrollment.
• Handle inbound inquiries across phone, chat, SMS, and email with professionalism and empathy. You'll also make outbound calls to warm leads — people who have already expressed interest through our website — so every conversation starts with someone who wants to hear from you.
• Stay sharp and engaged through high call volumes, maintaining quality and consistency from your first call to your last.
• Adapt quickly to process updates and policy changes communicated in writing. Our team moves fast and you'll be expected to stay current without always being pulled off the phones.
• • Collaborate with a team that's serious about quality. You'll receive regular coaching and QA feedback as a standard part of this role.

What You Bring

• Active Health Insurance License (required)
• Medicare sales experience — you know the landscape and can speak to it confidently
• A track record in sales, with proven ability to close
• Strong customer service instincts. You can stay calm, empathetic, and professional even when conversations are tough
• Comfort navigating multiple systems efficiently during live calls
• A self-starter mindset. You take initiative, manage your own performance, and don't need to be micromanaged to stay on track
• Ability to thrive in a fast-paced, metrics-driven environment where priorities and volume can shift day to day
• Proficiency with Windows, MS Office, and web-based tools

Why Healthpilot

• Meaningful work — every enrollment is a real healthcare decision for a real person
• No cold calling — warm inbound and outbound conversations with people who are already interested
• A team that invests in your performance through active coaching and feedback
• Be part of a mission-driven company simplifying healthcare for the people who need it most