Regional Sales Director

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Regional Sales Director based in United States.

This is an exciting opportunity for an accomplished sales professional to drive business growth within the self-funded healthcare benefits market across the Midwest. In this high-impact, quota-carrying role, you will develop strategic partnerships with brokers, consultants, and employer groups while expanding market presence and generating new revenue. You will collaborate with cross-functional teams to deliver innovative healthcare solutions that improve client outcomes and reduce costs. The position offers a dynamic, fast-paced environment where strategic thinking, relationship-building, and consultative selling are key to success. If you thrive on exceeding ambitious goals and influencing complex sales cycles, this role provides the opportunity to make a meaningful impact while advancing your career.

• Develop and execute strategic territory plans to generate new business opportunities and achieve or exceed regional sales targets across the assigned Midwest territory.
• Build, strengthen, and manage long-term relationships with brokers, consultants, employer groups, and other key stakeholders to drive pipeline growth and successful deal closures.
• Lead complex consultative sales cycles, presenting tailored healthcare and self-funded solutions that align with client needs and business objectives.
• Maintain accurate sales forecasts, pipeline reporting, and market insights while communicating revenue opportunities and risks to leadership.
• Partner closely with account management and internal teams to ensure seamless client onboarding, successful implementations, and high customer satisfaction.
• Contribute to continuous business improvement by sharing market intelligence, customer feedback, and collaborating on product and process enhancements.

Requirements

• Bachelor's degree or equivalent professional experience.
• Approximately 10 years of experience in employee benefits sales, healthcare services, or related commercial business development.
• Proven success selling complex, consultative solutions within the self-funded healthcare, TPA, or employee benefits market.
• Strong understanding of self-funded health plans, stop-loss programs, broker distribution models, and the broader employee benefits landscape.
• Established relationships within the broker and consultant community across the Midwest region.
• Demonstrated ability to manage strategic sales territories, develop business plans, and consistently achieve revenue goals.
• Excellent communication, negotiation, presentation, and relationship management skills.
• Highly collaborative, self-motivated, and comfortable working in a fast-paced, performance-driven environment.

Benefits

• Competitive base salary ranging from $140,000 to $180,000 annually, depending on experience and location.
• Performance-based bonus and variable compensation opportunities.
• Comprehensive medical, dental, and vision coverage beginning on day one.
• Mental health resources, wellness programs, and employee wellbeing initiatives.
• Flexible work arrangements to support work-life balance.
• Retirement planning support, life insurance, AD&D, and short- and long-term disability coverage.
• Voluntary benefits, including critical illness and hospital indemnity coverage.
• Unlimited paid time off policy.
• Professional development opportunities, mentorship, and ongoing learning support.
• Inclusive, collaborative workplace focused on innovation, growth, and employee success.