Role Description

Your North Star: Build, lead, and scale Pomelo’s payer sales organization to expand our impact nationwide.

The Head of Payer Sales will lead a team of Payer Sales Executives responsible for driving growth of new partnerships with health plans. You will be accountable to drive your team’s performance against partnership goals through efficient management of the full sales cycle by hiring and developing a high-performing, collaborative team, and leveraging data while ensuring consistent performance, coaching, and collaboration across the team.

In this role you will:

• Lead, hire, and coach a team of Payer Sales Executives to achieve and exceed individual and collective revenue goals
• Operationalize Pomelo’s payer go-to-market strategy, including segmentation, coverage models, and sales playbooks.
• Forecast, measure, and report on team and pipeline performance to inform leadership decisions.
• Establish clear metrics, rhythms, and accountability for pipeline management, deal progression, and cross-functional collaboration.
• Ensure consistent, high-quality storytelling and value articulation across all stages of the buyer journey.
• Support team in navigating complex organizational structures within payer accounts to accelerate deal velocity.
• Monitor payer market trends, emerging models, and competitive activity to inform strategy.
• Represent Pomelo externally at conferences and industry forums, strengthening our brand and visibility among payer stakeholders.

Who you are:

• 10+ years of experience in enterprise sales, growth, or business development, with at least 4+ years leading a high-performing sales team
• Proven track record of building and managing high-performing sales organizations into a marketplace environment, ideally with a health or wellness orientation.
• Strategic thinker who can translate business goals into actionable sales strategies and operational plans.
• Exceptional leadership and coaching skills — able to hire, motivate, develop, and retain top-performing team members.
• Data-driven and results-oriented, with strong command of sales metrics, forecasting, and operational rigor.
• Excellent communication and executive presence; comfortable engaging with C-level stakeholders internally and externally.
• Adaptive, entrepreneurial, and pragmatic — you balance vision with disciplined execution.

Bonus points if you have any of the following

• 4+ years leading teams selling into health plans.
• Experience scaling a sales team at a high-growth startup.
• Deep network within national and regional health plans.
• Familiarity with Medicaid, managed care, or value-based contracting.

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 minimum base salary range is $200,000-$220,000, 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.

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