Regional Vice President, Sales

Accountabilities:: Develop and execute a regional sales plan designed to achieve revenue and growth objectives across the assigned territory. Build and strengthen trusted relationships with insurance brokers and employee benefits consultants, serving as a strategic advisor and resource. Educate broker partners on self-insurance and alternative healthcare funding models and help them identify employers that could benefit from these solutions. Identify and develop new business opportunities by understanding prospective employers’ needs, challenges, risk profiles, and healthcare objectives. Present tailored solutions that demonstrate how cost-control programs can reduce risk, improve cost efficiency, and generate meaningful savings. Lead sales presentations, broker meetings, group sessions, and other customer-facing engagements to communicate value and drive action. Maintain a strong regional pipeline and consistently pursue opportunities to achieve and exceed sales targets. Collaborate with account management, underwriting, marketing, and other internal teams to develop customized solutions and deliver a cohesive customer experience. Use market knowledge and data-driven insights to guide territory strategy, prioritize opportunities, and strengthen sales execution. Represent the organization at industry events, broker meetings, networking activities, and other relevant engagements. Maintain accurate sales activity, opportunity, and relationship information within Salesforce or another CRM platform. Contribute market intelligence, customer feedback, and competitive insights to internal teams to support broader business development and growth strategies. Requirements: 5+ years of experience as a consistent top-performing seller within self-insurance, self-funded benefits, stop-loss insurance, alternative funding, or a related market. Proven ability to develop and maintain strong, trust-based relationships with insurance brokers and employee benefits consultants. Established broker network and strong consultative selling capabilities. Demonstrated track record of consistently achieving or exceeding sales targets. Exceptional presentation, negotiation, communication, and relationship-building skills, with the ability to influence senior decision-makers and inspire action. Strong business development and relationship management capabilities. Ability to quickly interpret data and translate complex information into clear insights that support business decisions and sales outcomes. Strong familiarity with Salesforce or comparable CRM platforms and the ability to use technology to manage opportunities and drive results. Self-starter mentality with a strong sense of ownership, urgency, and commitment to winning. Bachelor’s degree in Business, Finance, or a related field. Ability and willingness to travel at least 50% within the assigned territory, along with some domestic travel for company events. Authorized to work in the United States without current or future employment visa sponsorship. Comfortable working in a high-growth, mission-driven environment and taking initiative in complex or evolving situations. Benefits: Competitive base salary plus incentive compensation. 100% employer-paid medical, dental, vision, disability, and life insurance benefits. Flexible paid time off. Generous company 401(k) contribution. Fitness reimbursement. Tuition reimbursement. Professional development stipend. Up to $1,000 per year in donation matching for qualified organizations. Opportunity to work with a fast-growing, mission-focused team. Opportunity to make a meaningful impact on how small and midsize employers manage healthcare costs and benefits. Field-based role centered on the San Antonio territory, with frequent local travel and additional domestic travel for company events.