Regional Sales Director (Remote)

Compensation: Base Salary: $100,000 – $130,000 USD On-Target Earnings: $255,000 – $275,000 USD Commission: Uncapped, with additional incentives for exceeding goals. About the Role: Our client seeks a highly motivated Mid-Market Regional Sales Director to drive growth in benefits solutions, including HSA, FSA, HRA, Lifestyle Spending Accounts, COBRA, and more. This role targets employee benefits brokers managing clients with 100-2,000 employees and involves establishing new relationships while leveraging existing networks.

The ideal candidate will execute a mix of transactional and solutions-oriented sales strategies, adapting to various prospects and maximizing revenue potential. Candidate must have a broker network, and prior relationships in place.

Key Role Highlights: Location: The candidate will reside in the Chicago market. Responsibilities: No direct reports; role emphasizes conducting demos, presentations, face-to-face meetings, and Lunch-and-Learns. Industry Requirement: Must come from the benefits industry with a strong background in health insurance or employee benefits. Broker Network: Existing broker relationships are required; the candidate must have a network already in place to leverage.

Key Responsibilities: Drive new HSA and benefits product sales within the assigned territory. Manage all sales activities to meet or exceed quotas and activity metrics. Conduct inbound and outbound outreach to employee benefits brokers. Host engaging presentations, demos, and Lunch-and-Learns to showcase solutions. Build and maintain strong relationships with brokers and other stakeholders. Map decision-makers and influencers to close deals efficiently. Provide market feedback to refine sales strategies and ideal customer profiles.

Skills & Experience Required: 5+ years in outbound sales within the benefits industry, specifically through the employee benefits broker channel. Proven track record of exceeding quotas and activity metrics. Proficiency with Salesforce CRM and other sales automation tools (e.g., Gong, ZoomInfo). Strong understanding of health insurance and employee benefits, including Consumer-Driven Health solutions. Existing broker relationships within the Chicago market and beyond. Excellent presentation, communication, and interpersonal skills. Ability to thrive in a fast-paced, dynamic environment.

About The Company

Our client is a remote-first, innovative benefits solutions provider headquartered in San Francisco, with a mission to improve personal and financial wellness through modern, user-friendly products. Their top-rated HSA and expanded suite of benefits empower companies and individuals alike.

Why Join? Exceptional customer satisfaction scores, exceeding industry standards. Cutting-edge technology designed for ease and reliability. Robust education and resources to boost adoption and usage. Opportunities to make a meaningful impact in an inclusive, supportive culture. If you’re ready to leverage your broker network and drive growth in the benefits industry, apply today!