Sales Director
MASA (Medical Access & Service Advantage) · masaaccess.com
ChicagoRemoteDirector4+ yrsContract
The job in short
Sales directing.
InsuranceCompliance
Details
- Found
- 25 d ago · posted 2026-08-27
- Location as listed
- Chicago, IL, US
- Role
- Executive / Director
- Source
- The company’s own careers site
Full description
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!
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