Strategic Partnerships Director, Labor & Trust

About the role

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.

Responsibilities

• 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%)
• 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)

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