Head of Sales

Head of Sales Welldoc is at the forefront of digital health, driven by a powerful mission: empowering better cardiometabolic health through AI-powered, personalized digital tech, with a vision to be the leading advanced AI digital technology partner across the healthcare industry. We're a team passionate about leveraging cutting-edge science to improve lives, united by core values of collaborative innovation, accountability to excellence, customer focus, efficiency, and unwavering integrity, quality, and safety. At Welldoc, you'll thrive in a collaborative and innovative environment where your contributions directly impact our mission. Recognized as a Great Place to Work for the past four years and named to Modern Healthcare’s Best Places to Work 2025, as well as being an industry thought leader featured at SXSW and in the Wall Street Journal and Economist, we invite you to make a real difference in healthcare with us. Job Purpose Reporting to the COO, the Head of Sales will design and execute our enterprise sales evolution. You will lead our next chapter of expansion by transforming complex sales cycles into a predictable, repeatable, and high-performing revenue stream. You will build structure, rigor, and accountability into the sales motion while personally leading large strategic accounts. This is a hands-on executive role requiring deep experience selling complex healthcare solutions with 9–24 month sales cycles. Candidates commutable to the Columbia, MD area will be expected to follow a hybrid work schedule. What You Will Own Revenue Acceleration & Predictability Deliver annual new ARR targets with disciplined forecasting Build and sustain a robust sales funnel, maintaining a 3x–4x pipeline coverage model to ensure long-term target attainment and market penetration. Systematically identify and remove friction in the sales process to increase overall win rates and strategically compress complex sales cycles. Champion a "Growth-at-Optimal-Cost" mindset, ensuring that revenue expansion is achieved through sustainable unit economics and efficient resource allocation. Establish quarterly board-ready revenue reporting and strategic insights. Enterprise Market Expansion Own strategy and execution across: National & regional health plans Large PBMs ACO’s and Health Systems State Entities in support of the Rural Health Transformation Program Fortune 1000 self-funded employers Consultant-driven employer channels Develop segmentation strategy and account prioritization model. Building a Scalable Sales Engine This role will be responsible for transforming the current sales function into a world-class, repeatable revenue engine designed for rapid scale: Recruit and develop Regional VPs and Enterprise Directors Deploy a rigorous, structured sales methodology tailored to the unique complexities of the 9–24 month healthcare sales cycle. Standardize: Qualification criteria Deal desk governance RFP management Pricing discipline Institute a data-driven management rhythm, including disciplined weekly pipeline reviews and comprehensive Quarterly Business Reviews (QBRs), to ensure total team accountability. Strategic Deal Leadership As a hands-on executive, the Head of Sales will bridge the gap between high-level strategy and tactical execution for our most critical accounts: Personally lead top 10 strategic enterprise deals Architect and negotiate sophisticated value-based and outcomes-oriented contract models that ensure mutual long-term success. Navigate complex sales process including: clinical, actuarial, product development, pharmacy, and procurement stakeholders Translate Welldoc’s complex AI capabilities into clear, compelling narratives aligned with the industry's most pressing clinical and financial priorities including:Medical cost reduction GLP-1 optimization strategy Cardiometabolic risk reduction Quality improvement and Stars/HEDIS impact Cross-Functional Leadership Success in this role requ ... (truncated, view full listing at source)