Head of Sales

Job Title: Head of Sales Company: CheckRx Location: Chula Vista, CA (On-site) Job Type: Full-time Travel Required: Yes (Regional/National) Compensation: $70,000 + Commission About CheckRx CheckRx is a digital health and data intelligence platform that simplifies Medicare plan comparison, prescription coverage insights, and decision-making for Medicare beneficiaries and the agents who serve them. The company's tools leverage technology to streamline access to prescription and Medicare Part D benefit information, empowering users with clearer choices and cost savings. Role Summary The Head of Sales at CheckRx is a senior leadership position responsible for defining and executing the company's sales strategy, scaling revenue, and building a high‐performing sales organization aligned with the company's mission and business goals. This role reports to the CEO and works cross‐functionally with marketing, product, and operations to drive growth, expand market presence, and establish long‐term partnerships in the healthcare and Medicare ecosystem. The ideal candidate combines strategic vision, operational excellence, and a deep understanding of SaaS or digital health sales in complex markets. Key Responsibilities Direct Selling & Deal Closing: Take a hands-on approach to the sales cycle. Personally lead and close complex, high-value enterprise agreements and partnerships. Strategic Sales Leadership: Develop and implement a comprehensive sales strategy that drives revenue growth, expands market share, and supports CheckRx's long‐term business objectives. Revenue Growth & Target Achievement: Set ambitious but attainable sales targets. Monitor performance and adjust strategies to ensure the company hits revenue goals. Sales Organization Development: Recruit, train, and mentor a high‐caliber sales team. Establish a culture of high performance, accountability, and continuous improvement. Pipeline Management: Oversee sales pipeline development and forecasting with accuracy. Ensure the pipeline is sufficient to meet quarterly and annual closing targets. Cross‐Functional Collaboration: Work closely with Marketing to align messaging and lead generation. Partner with Product teams to incorporate customer feedback. Executive Reporting: Communicate sales strategy, closing progress, and challenges to the executive team and board. Required Qualifications Experience: 8–10 years of progressively responsible sales experience. Industry Preference: Experience within the Healthcare or Medicare space is highly preferred. Strategic Expertise: Ability to develop strategic sales plans that delivered measurable revenue growth. Team Leadership: Track record of building and scaling high‐performing sales teams. Data‐Driven Decision‐Making: Strong analytical skills; comfortable using CRM analytics to forecast outcomes. Excellent Communication & Negotiation: Strong interpersonal skills and ability to influence at all levels, including C‐suite executives and external clients. Preferred Qualifications Experience in Medicare, health insurance technologies, or healthcare services. Familiarity with HIPAA‐regulated environments and healthcare compliance considerations. Background in selling to enterprise and agency audiences. Why Join CheckRx? CheckRx operates at the intersection of technology and healthcare, enabling meaningful impact for millions of Medicare beneficiaries. As Head of Sales, you will play a pivotal role in shaping the company's commercial success, scaling a mission‐aligned product, and leading a growing sales organization in a dynamic, high‐growth environment.