Sales Director

MASA Global; Chicago (IL); Hybrid; USD 100,000 - 140,000; Full time

Benefits offered by this job

Competitive base salary

Bonuses

Benefits package

Job summary

MASA Global is seeking a motivated sales leader to manage a remote Illinois-based team of 1099 agents, reporting to the Regional VP of Sales. You will recruit, train, and oversee a sales force while driving strategy, coaching, and performance metrics.

This role emphasizes independence within a collaborative team culture. You will travel within the state to support seminars, generate leads, and ensure member enrollment and retention.

Qualifications

• 4+ years’ experience leading and managing 1099 sales teams.
• Solid health insurance industry knowledge, preferably Medicare.
• Strong sales management experience and analytical skills.
• Proven presentation skills in group or seminar settings.

Responsibilities

• Recruit, develop, and train a new 1099 independent sales agents team.
• Lead overall sales strategy, coaching, and development of the sales team.
• Provide continuous feedback on individual and team progress.

Skills

Sales leadership

1099 sales teams

Presentation skills

Interpersonal skills

Analytical skills

Driver's license

Education

College degree preferred

Job 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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