Head of Medicaid Payer Sales

About us Pomelo Care is the national leader in evidence-based healthcare for women and children. We deliver personalized, high-quality clinical interventions from reproductive care and pregnancy, infant care and pediatrics, to hormonal health through perimenopause and menopause, with long-term preventive care and condition management. Our model delivers 24/7 multispecialty care to address the medical, behavioral, and social factors that most significantly impact outcomes for women and children. We partner with payers, employers, and providers to expand access to quality healthcare across the system. Role Description Your North Star: Build, lead, and scale Pomelo’s Medicaid sales organization to expand our impact across the Managed Care landscape nationwide. The Head of Medicaid Sales will lead a team of Sales Executives responsible for driving new partnerships exclusively with Medicaid Managed Care Organizations (MCOs) and state health entities. You will be accountable for your team’s performance against growth goals by hiring a high-performing team that understands the nuances of the Medicaid regulatory environment, value-based contracting, and the unique needs of Medicaid beneficiaries. What You'll Do: Lead, hire, and coach a team of Medicaid Sales Executives to achieve and exceed revenue goals specifically within the Medicaid market. Develop and operationalize Pomelo’s Medicaid go-to-market strategy, including state-by-state segmentation, MCO coverage models, and specialized sales playbooks Forecast and report on pipeline performance, focusing on the long-cycle, high-impact nature of Medicaid contracting Establish clear metrics and accountability for end-to-end deal progression, from sourcing through negotiations and contracting to closed deals. Articulate Pomelo’s value proposition and differentiators effectively to win in the market Identify new opportunities to serve Medicaid and public sector segment customers Support the team in navigating the intricate organizational structures of national and regional Medicaid plans to accelerate deal velocity Monitor Medicaid policy shifts, including CMS rulings and state RFP cycles, to inform proactive sales strategies Represent Pomelo externally at Medicaid-focused conferences and events to build relationships and strengthen our brand among public sector stakeholders Who You Are: 10+ years of experience in enterprise sales or business development, with direct experience with Medicaid value-based payment (VBP) models and state-level procurement processes 4+ years of experience leading high-performing sales team Proven track record of building sales organizations that successfully sell into Medicaid MCOs or state-funded health programs Able to translate complex Medicaid policy and reimbursement shifts into actionable sales strategies A mentor who can hire, motivate, and retain talent capable of navigating the high-stakes Medicaid environment Outstanding relationship builder to develop new and manage existing relationships to facilitate Pomelo’s growth strategy Strong accountability for growth performance KPIs with a data-driven command of sales metrics and strategies Why you should join our team By joining Pomelo, you will get in on the ground floor of a fast-moving, well-funded, and mission-driven startup where you will have a profound impact on the patients we serve. And you'll learn, grow, be challenged, and have fun with your team while doing it. We strive to create an environment where employees from all backgrounds are respected. We value working across disciplines, moving fast, data-driven decision making, learning, and always putting the patient first. We also offer: Competitive healthcare benefits Generous equity compensation Unlimited vacation Membership in the First Round Network (a curated and confidential community with events, guides, thousands of QA questions, and opportunities for 1-1 mentorship) At Pomelo, we are committed to hiring t ... (truncated, view full listing at source)