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. About The Role: Your north star: 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. 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. 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%) Who you are: 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 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