Head of Health Plan Sales — Medicaid/Medicare (Remote)

Carex is partnering with a Food-as-Medicine industry partner to identify a Founding Head of Sales who will lead growth across the health plan market, with a strong focus on Medicaid, Medicare, D-SNP, and Medicare Advantage. This leader can live anywhere in the US and will own the strategy, structure, and execution of a complex enterprise sales process centered on disease management, medically tailored grocery solutions, food as medicine, and care navigation. The ideal candidate brings deep expertise selling into health plans, understands long and consultative healthcare sales cycles, and can clearly connect innovative solutions to measurable member engagement, quality, cost, and health outcome goals. This is a high-impact opportunity to build the sales function from the ground up and help scale a mission-driven growth-stage organization. Carex Consulting Group is an equal opportunity employer. We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, marital status, disability, gender identity, or Veteran status. What You’ll Do Build and execute a comprehensive sales strategy to drive expansion within Medicaid, Medicare, D-SNP, and Medicare Advantage plans. Establish target account criteria and create a high-quality pipeline of qualified enterprise health plan opportunities. Leverage existing relationships and develop new outreach strategies to generate demand and open doors with senior payer decision-makers. Lead full-cycle sales efforts from prospecting through signed contracts, managing complex and multi-stakeholder buying processes. Clearly articulate the value proposition of medically tailored grocery, disease management, and care navigation solutions to prospective clients. Develop and track sales KPIs, funnel metrics, dashboards, and reporting tied to company growth goals. Partner cross-functionally with operations, marketing, product, and engineering teams to ensure smooth handoff, onboarding, and long-term client success. Collaborate with marketing on collateral, campaigns, events, and thought leadership to support pipeline generation. Gather market feedback and translate insights into recommendations around product capabilities, positioning, and go-to-market strategy. Help shape company OKRs and own sales-related objectives that support overall business growth. What You’ll Bring Proven success selling into Medicaid, Medicare Advantage, D-SNP, health systems, or other complex healthcare enterprise buyers. Experience building and managing a pipeline of health plan prospects through long, strategic sales cycles. Background selling disease management, population health, digital health, tech-enabled services, SDoH, food as medicine, or related healthcare solutions. Experience building or leading a sales function within a high-growth, venture-backed startup environment. Demonstrated ability to scale commercial efforts from early product-market fit through accelerated growth stages. Strong executive presence with the credibility to engage payer leadership and C-suite stakeholders. Excellent communication and relationship-building skills across both internal and external audiences. Analytical mindset with the ability to synthesize market feedback and continuously improve sales effectiveness. Adaptability, resourcefulness, and comfort operating in a fast-paced builder environment. Compensation Annual base salary range: $180,000 - $220,000 , plus incentive compensation up to 100% of base salary . Additional benefits include equity, medical coverage, dental, vision, unlimited PTO, 401(k) with 3% employer contribution, and a $1,000 home office stipend. #J-18808-Ljbffr Carex Consulting Group