Medicare Operations Specialist, ISA

eHealth

1d • $65,300 - $81,600

About The Position

The ISA Operations Specialist serves as a primary operational, sales, training, and compliance resource for Independent Sales Agents within eHealth’s 1099 program. This role is responsible for providing day-to-day support related to systems, compliance, commissions, contracts, and live sales assistance. The ISA Operations Specialist also serves as a sales coach and training resource, helping agents develop their Medicare sales skills, improve performance, and confidently serve beneficiaries while maintaining adherence to company and regulatory requirements.

Requirements

• Experienced current or former eHealth Supervisor with the ability to manage Independent Sales Agents and multiple priorities in a fast-paced environment
• Well versed in Medicare and CMS regulations
• Strong verbal and written communication skills
• High attention to detail, particularly in compliance and documentation
• Strong collaboration and relationship-building skills
• Data-driven with experience using performance metrics
• Effective problem-solving and operational support skills
• Adaptable in dynamic sales environments
• Customer-focused with a commitment to quality agent support

Nice To Haves

• Additional insurance knowledge and sales experience, including life insurance, is a plus

Responsibilities

• Provide operational, sales, and compliance support to Independent Sales Agents within eHealth’s 1099 program
• Serve as a primary contact for agent inquiries related to systems, compliance, commissions, contracts, and sales support
• Deliver real time support via chat and Microsoft Teams office hours
• Host sales training and upskilling sessions for 1099 agents
• Maintain accurate agent records, compliance documentation, and Ready to Sell status
• Conduct compliance follow-ups and support corrective actions as needed
• Monitor agent performance and identify coaching, training, and live sales support opportunities
• Share agent feedback and insights to support continuous improvement of the ISA program
• Demonstrate eHealth’s core values in daily work and decision-making

Benefits

• Generous benefits including medical, dental, and vision beginning on your first day of employment
• 401(k) with company matching
• Tuition reimbursement
• Employee stock purchase program
• 12 company-paid holidays and flexible time off (PTO for non-exempt employees)

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed