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Company Mission

The Difference Card helps employers build more cost-effective health plans while maintaining high-quality employee benefits. Since 2001, our proprietary reimbursement, risk transfer, and wellness solutions have delivered an average net savings of more than 18% for clients nationwide. Through strategic broker partnerships and a consultative approach, we help employers reduce healthcare costs while improving outcomes.

Why Join The Difference Card

• Lead an established territory with significant growth potential.

• Join a proven, differentiated solution that delivers measurable healthcare savings.

• Enjoy a remote-first environment with competitive compensation and uncapped incentive opportunities.

Role Overview

As Midwest Market Director, you will lead sales growth within an assigned territory while managing and developing a team of Senior Sales Consultants. This player-coach role combines sales leadership, broker relationship management, and strategic business development. Reporting to the Vice President of Sales, you will be accountable for territory growth, team performance, pipeline development, and market expansion.

Success in this role will be measured by your ability to grow revenue, develop top-performing talent, expand broker relationships, and consistently achieve territory objectives.

Key Responsibilities

• Lead the overall business development, broker engagement, and sales growth strategy for the assigned territory.

• Recruit, coach, develop, and retain a high-performing team of Senior Sales Consultants.

• Drive achievement of market revenue, client acquisition, and pipeline goals through effective leadership and execution.

• Build and maintain strategic relationships with key brokers, consultants, and prospective clients.

• Partner with team members on large, complex, or strategic sales opportunities to maximize close rates and market growth.

• Coach, develop, and hold team members accountable for activity, pipeline, and sales performance goals.

• Maintain accurate forecasting and pipeline management through Salesforce, including regular pipeline reviews and opportunity strategy sessions.

• Ensure consistent execution of The Difference Card's consultative sales process and value proposition across the market.

• Partner with internal stakeholders to support growth initiatives and provide market insights that influence business strategy.

• Represent The Difference Card at broker meetings, industry events, conferences, and networking opportunities.

• Perform other duties as assigned.

Position Metrics

•Annual sales revenue attainment

•New client acquisition

•Pipeline coverage and forecast accuracy

•Team activity and productivity

•Sales consultant retention and development

•Salesforce data quality and compliance

Skills & Qualifications

•Bachelor's degree or equivalent professional experience

•Active State Health Insurance License or ability to obtain one within 90 days of hire

•5+ years of experience in health insurance, employee benefits, or a related industry

•5+ years of sales leadership experience building, coaching, and developing high-performing consultative sales teams

•Demonstrated success driving territory growth, market expansion, and achievement of sales objectives

•Established relationships within the employee benefits broker and consultant community, with a proven track record of generating new business opportunities

•Strong leadership, communication, presentation, and relationship management skills, coupled with a data-driven approach to decision making

•Proficiency with Salesforce, Microsoft Office Suite, and virtual meeting platforms

•Ability to travel approximately 25–50% within the assigned territory and periodically for company meetings and industry events.

Compensation: Base salary plus monthly incentive compensation based on the production of direct sales team and territory.

Location: Remote, with travel required

Job Type: Full-Time/Exempt

EB Employee Solutions, LLC is an Equal Opportunity Employer that does not discriminate on the basis of actual or perceived race, creed, color, religion, alienage or national origin, ancestry, citizenship status, age, disability or handicap, sex, marital status, veteran status, sexual orientation, genetic information, arrest record, or any other characteristic protected by applicable federal, state or local laws. We are dedicated to this policy with respect to recruitment, hiring, placement, promotion, transfer, training, compensation, benefits, employee activities and general treatment during employment.