Medical Access & Service Advantage

Sales Director

Chicago, IL

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hirly's read of this role

Role family: Sales
Seniority: Director
Stated salary: $100,000 per year
Country: US
Work mode: On-site / unstated
First seen by hirly: 25 Sept 2026

Derived automatically from the posting. Upload your resume above to see how the role scores against it.

the posting

Description

This is a remote, field-based position covering the state of Illinois. You must be based inside the territory.

Do you want to earn $100,000+ working for a company with an incredible track record and sales culture? How about being part of a team that values independence AND teamwork? Do you have a passion for working with seniors, retirees, and frequent travelers?

MASA is currently seeking a motivated and experienced person with a background in outside sales leadership. You will work from home/virtual office, traveling to various locations within the state. Your goal will be to enroll and retain current members.

About Us

MASA has been a leader in emergency medical transportation insurance since 1974. We're not just a company – we're a close-knit team dedicated to "Protecting families with compassion when others don't." Our professional yet friendly company culture fosters collaboration, innovation, and a clear mission that resonates through every role as we support our expanding base of 2+ million members across the United States and the Caribbean. Learn more at https://www.masamts.com

What You Will Do

Reporting to our Regional Vice President of Sales, you will develop and lead our sales team in your state. Your main responsibilities will include:

Recruit, develop, and train a new sales team of 1099 independent sales agents.
Lead the overall sales strategy, coaching, and development of the sales team.
Provide continuous feedback regarding individual and sales team progress.
Conduct sales seminars provided by the company as well as self-generate new leads and sales.
Coach on best practices for professional selling skills, effective supervision, and compliance.

What We Need From You

College Degree preferred.
4+ years’ experience and skills in leading and managing 1099 sales teams.
Previous and successful sales, leadership, and management experience.
Solid health insurance industry knowledge, preferably Medicare.
Strong sales management experience and analytical skills.
Proven presentation skills in group or seminar setting.
Exceptional interpersonal and communicative skills with both individuals and groups.
Driver's License (Required).
Insurance license NOT REQUIRED.

What We Will Provide You

Competitive base salary, bonuses, and comprehensive employee benefits programs.
A professional and friendly company culture that supports a clear mission: "Protecting families with compassion when others don’t."
An opportunity to unleash your expertise and create a lasting impact on our journey of growth and success!

#LI-RH1

Original posting on Medical Access & Service Advantage's site ↗

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