Strategic Partnerships Director, Labor & Trust

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. Role Responsibilities Pomelo is looking for an exceptional and experienced founding Strategic Partnerships Director, Labor & Trust. This is a full-cycle sales role responsible for driving new business with trustees, benefits managers, and union leadership–bringing 24/7 virtual maternal, pediatric and midlife care to working families nationwide. This position is integral to driving Pomelo revenue growth and furthering our mission by creating opportunities to serve more families. As a Strategic Partnerships Director, Labor & Trust at Pomelo, you will: Champion Pomelo's mission with enthusiasm and credibility, utilizing relationship building to drive market demand. Manage the entire sales cycle for Labor & Trust opportunities, from pipeline generation through contract close. Partner with BDR to source and close new opportunities Lead consultative sales conversation with trustees and benefits managers - uncovering needs, aligning on outcomes and tailoring Pomelo’s value proposition Assess and engage decision-makers, influencers, and champions, crafting persona-specific strategies to deliver value in every interaction. Develop a detailed plan for meeting your individual sales targets. Consistently meet and exceed sales targets by focusing on strategic, high-value accounts Represent Pomelo at labor conferences, trustee summits and industry events (travel ~30%) What you'll do 8+ years of direct sales experience with strong track record of quota attainment,, including at least 5 years selling benefits, healthcare or SaaS solutions to labor and trust clients Deep understanding of union benefit structures, trust governance, and decision-making processes. Proven track record of closing 6-figure+ enterprise deals and consistently achieving quota. 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 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 on-target earnings for this role is $330,000-$350,000 per year. 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. 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.