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Director, Employer Sales

United States

About us

Pomelo Care is a multi-disciplinary team of clinicians, engineers and problem solvers who are passionate about improving care for moms and babies. We are transforming outcomes for pregnant people and babies with evidence-based pregnancy and newborn care at scale. Our technology-driven care platform enables us to engage patients early, conduct individualized risk assessments for poor pregnancy outcomes, and deliver coordinated, personalized virtual care throughout pregnancy, NICU stays, and the first postpartum year. We measure ourselves by reductions in preterm births, NICU admissions, c-sections and maternal mortality; we improve outcomes and reduce healthcare spend.

Role Description

Your North Star: Grow and accelerate Pomelo’s employer pipeline by developing strong client relationships, designing go-to-market strategies, and structuring and negotiating contracts that are both compelling and scalable. 

In this role, you will own the end-to-end sales process for mid-sized, large and jumbo employers, driving market demand, crafting tailored prospect and buyer-level strategies, and managing the full sales cycle. This position is integral to driving Pomelo revenue growth and furthering our mission by creating opportunities to serve more patients.

Responsibilities: 

  • Champion Pomelo's mission with enthusiasm and credibility, utilizing relationship building to drive market demand.
  • Develop and execute a detailed plan to meet individual sales targets.
  • Build and manage a high-quality pipeline to deliver on employer growth targets to support Pomelo’s overall growth strategy. 
  • Secure meetings with employer buyers at all levels, from C-suite executives to health benefits managers, using creativity and persistence.
  • Position Pomelo’s value proposition effectively, tailoring approaches based on competitive insights, technology, and individual buyer needs.
  • Assess and engage decision-makers, influencers, and champions, crafting persona-specific strategies to deliver value in every interaction.
  • Manage the full end-to-end sales process including negotiation and contracting to pull pipeline opportunities through to signed deals.
  • Collaborate with Partnerships and Marketing teams on pitches, conferences, and presentations to source and develop new prospects and maximize impact on pipeline opportunities.
  • Develop compelling presentation and proposal materials for growth opportunities and advocate for prospective customer needs internally.
  • Analyze pipeline data and refine operational processes to accelerate partnerships and support Pomelo’s growth trajectory.

Who You Are:

  • 7+ years of direct sales experience, including at least 3-5 years selling to benefits leaders or similar functions within large employers (10K+ employees), with a documented history of exceeding quotas and delivering results.
  • Demonstrated ability to lead complex end-to-end sales processes, with exceptional organizational skills and proficiency in using tools like Salesforce to manage deals and follow-ups.
  • Strong written, verbal, and presentation abilities, capable of distilling complex information into clear, compelling messaging for diverse audiences.
  • Adaptive, pragmatic, and eager to thrive in a fast-paced, metric-driven startup environment with competing priorities.
  • Familiarity with the healthcare system and digital health space, including industry and competitive trends, paired with a willingness to research and learn new domains.
  • Experience managing cross-functional projects, problem-solving across teams, and turning ideas into actionable strategies.
  • A mindset focused on continuous improvement and a relentless drive for success.
  • Regular travel is expected to support partnership and business development initiatives.

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 current salary range is $165,000-$180,000 plus a bonus. We expect most candidates to fall in the middle of the range. 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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