About us Pomelo Care is the leading virtual medical practice for women and children, providing care across pregnancy, postpartum, pediatrics, menopause, and perimenopause. We combine proactive, 24/7 clinical care with technology that helps us reach patients earlier, identify risks sooner, and deliver personalized care throughout their journey. Our team includes clinicians, technologists, operators, and problem-solvers working together to make high-quality care more accessible for families nationwide. About The Role Your North Star: In this role, you will spearhead our growth with the nation's largest employers. You will own the end-to-end sales process for large and jumbo employers, driving market demand, crafting tailored prospect and buyer-level strategies and proposals 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 families. This role reports to the Head of Employer Sales and is open to any candidates located in the continental US. What You’ll Do • Champion Pomelo's mission with enthusiasm and credibility, utilizing relationship building to drive market demand. • Develop a detailed plan for meeting your individual sales targets. • Secure meetings with employer buyers at all levels, from C-suite executives to benefits leaders, using creativity and persistence. • Position Pomelo’s value proposition effectively, tailoring approaches based on competitive insights and individual buyer needs. • Assess and engage decision-makers, influencers, and champions, crafting persona-specific strategies to deliver value in every interaction. • Work collaboratively with our channel partners (e.g., national and regional health plans, benefits consultants) to drive an efficient and consultative sales process. • Drive and achieve sales goals, including management of the entire end-to-end sales process. • Travel as needed for conferences, prospect meetings, and to engage with brokers/consultants. Who You Are • 10+ years of direct sales experience, including at least 5 years selling to benefits leaders or similar functions within large employers (25K+ 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. 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 that always puts the patient first. You will learn, grow and 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. Benefits and Perks: • Comprehensive Health, Dental, and Vision coverage for employees and their families • High deductible Health Plans with Health Savings Account (HSA) options • Flexible Spending Account (FSA) • Equity grant participation • 401(k) program • Competitive vacation policy • 16 weeks paid parental leave • Fully remote work flexibility (within the US) Compensation: The expected base salary range for this role is $165,000-$185,000. This role is also eligible for variable compensation, with expected on-target earnings of $330,000 to $370,000, and equity, giving you an ownership stake in Pomelo’s mission. Actual compensation may vary based on relevant experience, skills, competencies, and certifications. 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. 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 [email protected] to confirm its legitimacy. For your safety, we also recommend applying only through our official Careers page. If you believe you have been the victim of a scam or identity theft, please contact your local law enforcement agency or another trusted authority for guidance.