Regional Sales Executive, Group Benefits

Description

This is a full-time, field sales position based in Chicago, IL

Compensation base salary + commissions + bonuses typically range from $140,000 to $300,000+ per year

MASA is hiring a Regional Sales Executive to grow our Group Benefits business. This role is for someone who enjoys building broker relationships, growing their market, and helping employers understand a benefit they may not have considered before.

Emergency ground and air transportation can leave employees with significant out-of-pocket costs, even when they have health coverage. MASA helps protect members from eligible emergency transportation expenses. You'll work with benefits brokers and employers to identify where that exposure exists, build a clear, data-informed case for addressing it, and determine how MASA fits into an employer's benefits strategy.

Your primary focus will be the above market and surrounding areas. There may also be opportunities to work through established broker relationships elsewhere, subject to territory and account coordination.

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

What You Will Do

Reporting to the Regional Vice President, Group Benefits Sales - East, you will:

• Build and deepen productive relationships with benefits brokers and consultants across the market, turning them into advocates who bring you into new employer conversations.
• Develop your own pipeline through broker outreach, employer prospecting, referrals, and local market activity. Create demand as well as respond to opportunities.
• Lead discovery with brokers and employers to understand their workforce, health plan design, funding approach, renewal timing, and emergency transportation exposure.
• Build a clear, data-informed business case for MASA and successfully present solutions to HR and finance leaders.
• Explain clearly and accurately how MASA works alongside the health plan, including the funding options and considerations for employer-paid and voluntary offerings.
• Tailor proposals and presentations to each broker and employer.
• Manage opportunities from first conversation through proposal, decision, enrollment planning, and handoff to Implementation and Account Management, setting clear expectations along the way.
• Develop broker and account plans, keep CRM current and accurate, and provide an informed view of your pipeline and forecast.
• Partner with Sales leadership, Marketing, Sales Operations, and Implementation, and share what you learn in the field with your peers.
• Travel regularly to meet brokers, employers, and other partners throughout the market.

What You Bring

• At least five years of successful employee benefits sales experience, including substantial experience selling through brokers or consultants.
• A record of building new business, with examples of opportunities you sourced and advanced yourself.
• Established relationships with benefits brokers in the assigned market and the ability to develop relationships beyond your existing network.
• Consultative selling skills: uncover a problem, quantify its financial and human impact, and earn a clear next step with brokers and employers.
• Comfort using data to build a value case for cost-conscious buyers.
• The ability to learn nuanced topics quickly and explain them accurately.
• Experience navigating benefits decisions involving HR, finance, leadership, enrollment partners, or other stakeholders.
• A collaborative, team-oriented approach to selling.
• Strong territory planning, follow-through, presentation, and CRM habits.
• Curiosity about new sales tools and approaches, including AI.
• An active Accident and Health insurance license.
• Experience with voluntary or supplemental benefits, group life or disability, employer-paid benefits, self-funded employers, public sector groups, or healthcare organizations is valuable. We're most interested in what you've built and how you built it.

Why We Think You’ll Love This Opportunity

You'll have the opportunity to develop a market around a distinctive benefit with a clear purpose: helping protect families when emergency transportation creates an unexpected financial burden.

MASA offers a competitive base salary, commission and bonus opportunities, and benefits that include medical, dental, vision, a 401(k) with company match, paid time off, company-paid disability and basic life insurance, and a MASA membership.

NOTE: Any pay range listed for this position is an estimate by the job board and may not reflect the actual compensation.

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