Medicare Sales Specialist (Telephone) – 1099 Contractor

About the role

We are seeking high-performing Telephone Medicare Sales Specialists who know how to take control of a call, build trust quickly, and close consistently. This is a full-cycle, phone-based sales role where your ability to connect, consult, and convert directly determines your income.

Responsibilities

• Handle inbound and outbound calls with a consultative, closing mindset
• Build rapport quickly and control the conversation with confidence
• Identify client needs, concerns, and eligibility
• Full-Cycle Sales Execution: Present plan options clearly and professionally, compare coverage, pricing, and benefits, overcome objections and guide clients to informed decisions, close enrollments efficiently and compliantly
• Compliance & Documentation: Maintain 100% CMS and carrier compliance on every call, accurately document all interactions in CRM systems, ensure all enrollments meet regulatory standards
• Performance & Optimization: Consistently hit or exceed application and revenue targets, maximize cross-sell and ancillary opportunities on each qualified call, continuously improve scripts, rebuttals, and closing techniques

Requirements

• Required 3–5+ years of sales experience (B2C or B2B)
• Proven track record as a closer
• Strong communication and objection-handling skills
• Ability to work remotely in the U.S.
• Tech-savvy with the ability to multitask across systems

Qualifications

• Active Health Insurance License (preferred, not required for strong candidates)
• Current AHIP certification (or willingness to obtain prior to start)
• Ability to become Ready-To-Sell (RTS) with multiple carriers

Skills

• Competitive and results-driven mindset
• High level of personal accountability
• Coachable and open to feedback
• Disciplined with strong daily activity habits
• Professional, ethical, and compliance-focused

Benefits

This is not a typical call center position. You are not just taking calls—you are: Running full-cycle sales conversations, Building real income based on performance, Top performers in this role treat every call as an opportunity to: Solve real problems for seniors, Deliver clear, valuable solutions, Maximize earnings through skill and consistency, Work Environment: Fully remote, phone-based role, Independent, performance-driven structure, Fast-paced sales environment with ongoing coaching and support

Pay

Up to $350 per successful application

Schedule

Independent, performance-driven structure