Head of Medicaid Sales

Job Application for Head of Medicaid Payer Sales at Pomelo Care Head of Medicaid Payer Sales United States Apply About us At Pomelo Care, we are redefining the healthcare journey for women and children. As the leading virtual medical practice in our field, we provide a continuous circle of support—from the first steps of family building and the complexities of pregnancy to the nuances of postpartum, pediatric, and midlife care. We aren't just a clinic; we are a multidisciplinary engine of clinicians, engineers, and problem-solvers dedicated to closing the gaps in traditional care. By leveraging a high-touch, technology-driven platform, we identify risks early and deliver deeply personalized, 24/7 virtual care. We are here to prove that better data and patient-centered care lead to better outcomes, raising the standard of care for families nationwide. 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 Q&A questions, and opportunities for 1-1 mentorship) At Pomelo, we are committed to hiring the best team to improve outcomes for all mothers and babies, regardless of their background. We need diverse perspectives to reflect the diversity of problems we face and the population we serve. We look to hire people from a variety of backgrounds, including but not limited to race, age, sexual orientation, gender identity and expression, national origin, religion, disability, and veteran status. Our salary ranges are based on paying competitively for our company’s size and industry, and are one part of the total compensation package that also includes equity, benefits, and other opportunities at Pomelo Care. In accordance with New York City, Colorado, California, and other applicable laws, Pomelo Care is required to provide a reasonable estimate of the compensation range for this role. Individual pay decisions are ultimately based on a number of factors, including qualifications for the role, experience level, skillset, geography, and balancing internal equity. A reasonable estimate of the OTE range for this role is $400,000-$420,000, with meaningful variable compensation. We also believe that your personal needs and preferences should be taken into consideration, so we allow some choice between equity and cash. Potential Fraud Warning Please be cautious of potential recruitment fraud. With the increase of remote work and digital hiring, phishing and job scams are on the rise with malicious actors impersonating real employees and sending fake job offers in an effort to collect personal or financial information. Pomelo Care will never ask you to pay a fee or download software as part of the interview process with our company. Pomelo Care will also never ask for your personal banking or other financial information until after you have signed an offer of employment and completed onboarding paperwork that is provided by our People Operations team. All official communication with Pomelo Care People Operations team will come from domain email addresses ending in @pomelocare.com. If you receive a message that seems suspicious, we encourage you to pause communication and contact us directly at to confirm its legitimacy. For your safety, we also recommend applying only through our official Careers page. 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