Regional Vice President, Mid Market Sales

The Company is seeking a Regional Vice President, Mid Market Sales to develop new business with self-insured employers and grow its presence across the employer market. This individual contributor will build and manage a territory pipeline through proactive prospecting and partnerships, lead consultative discovery, and tailor recommendations and business cases to customer needs. Responsibilities include owning the full sales cycle from qualification through contract closure, engaging senior stakeholders, maintaining deal momentum, and achieving sales targets. The role also requires accurate forecasting, current CRM records, and close collaboration with consultants, health plan partners, and internal teams. Candidates should have experience selling health or benefits solutions to self-insured employers, a record of generating pipeline through outbound prospecting, and success winning new business and meeting quotas. Strong discovery, solution-based selling, negotiation, presentation, communication, and listening skills are essential, along with experience navigating complex sales cycles and engaging Benefits, HR, and Finance executives. Applicants should be self-directed, resilient, adaptable, and experienced working with benefits consultants and health plan account managers; experience at an emerging-growth company is also valued. A bachelor’s degree is required.