Medicare - Ancillary Sales Agent (Remote)

Top Talent. Real Freedom. Maximum Payouts!

Are you a closer who thrives on high-intent conversations and maximizing every opportunity? At WiseChoice, we're building a next-generation sales force of entrepreneurial agents who know how to convert inbound demand into real revenue.

As an Ancillary Sales Agent, you'll specialize in selling hospital indemnity and dental products (UNL + Dental Shield) while capitalizing on inbound lead flow and cross-selling Medicare Advantage and Final Expense opportunities. This is a high-earning role for agents who know how to listen, position value, and close.

At WiseChoice, our mission is to guide consumers through their health and financial protection options—when, where, and how they prefer. We're building a transparent, agent-first platform where performance is rewarded and freedom is real.

This position is fully remote

Quick Facts About WiseChoice Senior Solutions

• Founded: April 2024
• Mission: Redefining Medicare by putting people first (Talent & Senior) , one WiseChoice at a time.
• Vision: Earn More. Work Less. No Micromanagement.
• Traction: One of the fastest growing insure-tech start-ups teams.
• Key investors: Innovative Financial Group (IFG), FYM Financial, Humana
• Team size: 40 + agents & full-time equivalent (April 2025) and targeting 200+ by end of 2027
• Location: 100% remote (US required, preferably Midwest/Kansas City)

What you'll do:

As an Independent Ancillary Sales Agent, you will:

• Handle 100% inbound, high-intent leads—no cold calling
• Educate consumers on hospital indemnity and dental coverage (UNL, Dental Shield)
• Identify coverage gaps and position ancillary products as financial protection solutions
• Cross-sell Medicare Advantage and Final Expense when appropriate
• Build trust quickly through consultative conversations and needs analysis
• Accurately document and submit applications using WiseChoice systems
• Stay compliant with all carrier and CMS guidelines
• Maximize each call by increasing average revenue per lead (ARPL)

What we offer:

• Freedom with Accountability – “You control your schedule. We give you tools, not rules.”
• Transparent Commissions – “No games. No deductions. Real numbers paid fast.”
• Tech that Works – “CRM + dialer + automation built to help you sell, not slow you down.”
• Exclusive Lead Flow – “Qualified leads, real intent, never recycled.”
• Agent-First Culture – “No meetings, no micromanagement, just performance and partnership.”

Compensation:

• High commission payouts per policy sold (HI + Dental)
• Residual income opportunities on ancillary products
• Cross-sell earning potential (Medicare Advantage + Final Expense)
• Highest commission payouts in the industry. Top agents are making 200K+ annually working atleast 25+ hours weekly. Paid up to $300 per Medicare policy submitted.
• Ability to cross sales ancillary products like Dental Vision & Hearing (DVH), Cancer, and Hospital Indemnity (HI) that pay residual income.

Who you are:

• 12+ months of insurance sales experience (ancillary, life, health, or Medicare preferred)

• Strong closer with a track record of high conversion rates on inbound leads

• Comfortable cross-selling multiple products in a single call

• Entrepreneurial mindset with a focus on maximizing earnings per opportunity

• Competitive, self-driven, and resilient in overcoming objections

• Active Health and/or Life Insurance License (or ability to obtain quickly)

• Ability to secure carrier appointments (UNL experience is a plus)

You'll Need:

Equipment Requirements (You provide your own):

Windows

• Windows 11 (22H2 or later)
• 8GB RAM minimum (16GB recommended)
• 20GB available storage

Mac

• macOS Sonoma 14.7.2 or later
• 8GB RAM minimum (16GB recommended)
• 20GB available storage

Hours:

To maximize success, availability during peak inbound hours is strongly recommended:

• Off Season: Monday–Friday: 8:00 AM – 7:00 PM CST
• AEP Season: Monday–Friday: 8:00 AM – 8:00 PM  Weekends: 10:00 AM – 1:00 PM CST

About Us:

WiseChoice was founded in 2024 , and we're more than just a company—we're a team dedicated to simplifying Medicare for seniors nationwide. Built by Agents for Agents. With a focus on integrity, innovation, and exceptional service, we empower our agents to succeed while making a real impact. Join us and be part of a supportive culture that puts you first. Ready to Get Started? If you're driven to succeed and passionate about helping others, we want to hear from you!