Job Overview
Location
USA Remote
Job Type
Full-time
Category
Operations
Date Posted
June 20, 2026
Full Job Description
đź“‹ Description
- • The Medicare Operations Specialist, ISA serves as a primary operational, sales, training, and compliance resource for Independent Sales Agents within eHealth’s 1099 program, playing a critical role in enabling agents to successfully connect consumers with quality Medicare coverage while ensuring adherence to regulatory and company standards.
- • Day-to-day responsibilities include providing real-time support via chat and Microsoft Teams office hours, serving as the primary contact for agent inquiries on systems, compliance, commissions, contracts, and sales support, hosting sales training and upskilling sessions, maintaining accurate agent records and compliance documentation, conducting compliance follow-ups, monitoring agent performance, and identifying coaching and live sales support opportunities to drive continuous improvement.
- • eHealthInsurance Services, Inc. is a mission-driven organization dedicated to guiding consumers through health insurance options with transparency and trust, supporting a diverse team of innovators who solve complex challenges while upholding core values of fairness, collaboration, and customer-centricity in a remote-first, inclusive work environment.
- • In this role, the individual will develop deep expertise in Medicare and CMS regulations, enhance coaching and training capabilities, strengthen operational and compliance workflows, and contribute to the scalability and effectiveness of the ISA program—positioning themselves for growth in healthcare operations, sales enablement, or Medicare-focused leadership roles.
🎯 Requirements
- • Experienced current or former Medicare Supervisor with proven ability to manage Independent Sales Agents and multiple priorities in a fast-paced environment
- • Strong verbal and written communication skills, with high attention to detail in compliance and documentation
- • Well versed in Medicare and CMS regulations, with experience using performance metrics to drive agent performance improvements
🏖️ Benefits
- • Generous benefits including medical, dental, and vision coverage beginning on the first day of employment
- • 401(k) plan with company matching contributions
- • Tuition reimbursement and employee stock purchase program to support long-term growth and financial wellness
- • 12 company-paid holidays and flexible time off (PTO for non-exempt employees)
Skills & Technologies
See exactly how your profile matches this role — strengths, skill gaps, and what to do about them.
About eHealthInsurance Services, Inc.
eHealthInsurance Services operates a leading online health insurance marketplace in the United States. The platform allows consumers to compare and purchase individual, family, small-business, Medicare, and dental plans offered by national and regional carriers. Licensed in all 50 states and D.C., the company provides decision-support tools, educational content, and licensed agent support. Established in 1997, it went public in 2006 and is headquartered in Santa Clara, California. Revenue is generated through commissions from insurers and enrollment fees, positioning eHealth as a key digital distribution channel for the U.S. health insurance industry.
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