Drive enterprise growth by closing partnerships with the nation’s largest employers and expanding access to life-changing maternal and infant care.
About Pomelo Care
Pomelo Care is a team of clinicians, engineers, and problem-solvers dedicated to improving maternal and newborn health at scale. Their technology-driven virtual care platform engages patients early, performs individualized risk assessments, and delivers coordinated support throughout pregnancy, NICU stays, and the first postpartum year. They measure success by reductions in preterm births, NICU admissions, c-sections, and maternal mortality—improving outcomes while lowering healthcare costs.
Schedule
- Full-time
- Remote (United States)
- Travel required for conferences, prospect meetings, and consultant engagements
Responsibilities
- Drive market demand by championing Pomelo’s mission and building strategic relationships with large and jumbo employers
- Own the end-to-end enterprise sales process, from prospecting through closing and contracting
- Build and execute territory and account plans that deliver against individual sales targets
- Secure meetings with HR and benefits buyers at all levels, including C-suite, through targeted outreach
- Tailor Pomelo’s value proposition using buyer-level insights, competitive intelligence, and persona-driven strategies
- Engage decision-makers, influencers, and internal champions to move deals forward
- Collaborate with national and regional health plans, brokers, and benefits consultants to streamline the sales cycle
- Maintain consistent pipeline hygiene using Salesforce and other tools for forecasting, follow-ups, and reporting
Requirements
- Ten or more years of direct sales experience, including at least five years selling to HR or benefits leaders at jumbo employers (25K+ employees)
- Documented track record of exceeding quotas within enterprise or strategic sales environments
- Proven ability to lead long, complex, multi-stakeholder sales cycles from outreach to signature
- Exceptional communication skills with the ability to simplify complex concepts for diverse audiences
- Strong organizational habits with mastery of tools like Salesforce for pipeline management
- Adaptable, pragmatic, and motivated to thrive in a fast-paced, metric-driven startup
- Familiarity with healthcare, digital health, or benefits ecosystems, with willingness to learn new domains
- Experience managing cross-functional initiatives and converting ideas into actionable strategies
Bonus Points
- Background selling in competitive markets with multiple vendors
- Experience supporting or selling through brokers and benefit consultants
- Experience in virtual care, digital health, or value-based care
Benefits
- Competitive healthcare benefits
- Generous equity compensation
- Unlimited vacation
- Membership in the First Round Network (events, mentorship, curated resources)
- Salary range: $165,000–$180,000 plus bonus
High-impact, relationship-driven, and core to Pomelo’s mission—perfect for a closer who knows how to win enterprise business and shape markets.
Happy Hunting,
~Two Chicks…