Seasonal Supervisor, Benefit Advisors

Join us in creating a better way!

At eHealth, our mission is to expertly guide consumers through their health insurance and related options when, where, and how they prefer. We’re creating a better way – one that’s transparent and trustworthy for both our consumers externally and our employees internally. 

Move your career forward while connecting countless people to the life- changing, quality care they deserve. Our diverse team of innovators supports one another in solving some of the toughest challenges. We’re always on the lookout for creative opportunities to do right by our customers, and each other. Together, we’re creating a better way to work, united by our common passion to make a difference.

At eHealth, our mission is to connect everyone with quality, affordable health insurance and Medicare plans. Not only do we serve individuals, families, and businesses with health, dental, and vision options, but through eHealth Medicare we connect customers with Medicare Advantage, Medicare Supplement Insurance, and Prescription Drug Part D plans. And we do it for a simple purpose – to protect our clients’ well-being for life. Our desire to offer our Medicare beneficiaries and caregivers a world-class experience is not just words on a page. It’s a commitment we take seriously.
 

Job Overview
eHealth is hiring a Seasonal Supervisor, Benefit Advisors who will develop and lead a Medicare Sales Team. This position is responsible for exceeding inbound sales goals and KPIs, while maintaining the highest quality standards. The ideal candidate will be someone that has a proven track record of leading, developing, and managing a sales team, and executing a team’s plan to meet or exceed sales targets. 

This is a Remote First position which can be performed from most locations in the US. Working out of one of our offices may be occasionally required.
 

The Seasonal role will begin August 4, 2025 and conclude on December 7, 2025.

What you will do:
 

Supervises, motivates, and tracks a sales team’s performance, productivity, and schedule adherence to drive quality results.

• Serves as first point of escalation for sale team on sales process and technical issues in a remote environment; coaches team on how to efficiently resolve any issues.
• Drives sales and revenue by ensuring sales team is assisting customers in making healthcare decisions over the phone effectively.
• Maintains a positive work environment that leads and supports a sales team while identifying any opportunities that may inhibit an individual’s or team’s performance.
• Directs the team and ensures compliant and quality customer experience interactions. 
• Identifies strengths and opportunities of sales team to ensure each team member receives individualized coaching, training, and career development.
• Exceeds monthly sales and performance goals.
• Preserves healthy cross-collaboration with supporting sales departments, including Sales Mastery University, Compliance, Enrollment, Member Loyalty, Training, and IT.
• Must be flexible in hours you are able to work (possible nights and/or weekends).
• Maintains communication and connection with sales team through emails, Microsoft Teams chat messages, Microsoft Teams video calls, and individual phone calls.
• Balances and prioritizes day-to-day activities and deadlines to ensure successful execution of eHealth’s mission and values.
   

Who you are: 

• 1 to 3 years’ Supervisory experience within a managed care of organization, health insurance carrier, third party administrator, or related industry
• 1 to 3 years’ experience in progressively responsible sales or customer service positions
• Equivalent combination of education and sales/account management experience will be considered. High school diploma required.

Your Preferred Qualifications:

• Health insurance resident state license; will need to obtain for employment
• Knowledge of Medicare sales and CMS rules and regulations a plus
• Strong oral and written communicator
• Proficiency in Microsoft Office products
• Bachelor’s Degree in Marketing, Sales, Business Administration, or related field preferred

Who you would report to:

• Manager, Benefit Advisors

Our Values: At eHealth, our core values guide our work:

• One Team
• Customer Centric
• Innovation
• Integrity
• Quality
• Accountability
• Relentless
• Financial Stewardship

*Please note the above is a summary of responsibilities; a full job description is available upon request. 

Job Application Deadline: July 7, 2025

NOTE: As a licensed position working within a regulated industry, all employees must undergo extensive background checks that will include criminal background and credit history reports. eHealth may deny employment to or terminate the employment of any applicant or employee for whom the results of the background checks prevent or adversely affect licensing or certification.

#LI-DC1

#LI-Remote

-

The base pay range reflects the anticipated pay range for this position. The actual base pay offered will depend on various factors including individual skills, experience, performance, qualifications, the department budget, and the location where work is performed. Base pay is one component of eHealth’s total rewards package, which also includes a monthly commission-based incentive plan, plus an array of benefits designed to support employees’ personal and professional wellness.

-

Base Pay Range -$51,200 - $74,000

-

Annual Commission Target -$40,000

eHealth is an Equal Employment Opportunity employer. It is our policy to provide equal opportunity to all employees and applicants and to prohibit any discrimination because of race, color, religion, sex, national origin, age, marital status, sexual orientation, genetic information, disability, protected veteran status, or any other consideration made unlawful by applicable federal, state or local laws. The foundation of these policies is our commitment to treat everyone fairly and equally and to have a bias-free work environment.