Strategic Partnerships Director, Labor & Trust

Responsibilities

• Manage the entire sales cycle for Labor & Trust opportunities, from pipeline generation through contract close
• Lead consultative sales conversations with trustees and benefits managers to align Pomelo’s value proposition with their needs
• Partner with BDRs to source and close new opportunities
• Develop and execute detailed plans to meet and exceed individual sales targets
• Represent Pomelo at labor conferences, trustee summits, and industry events
• Assess and engage decision-makers, influencers, and champions using persona-specific strategies

Requirements

• 8+ years of direct sales experience with a strong track record of quota attainment
• 5+ years of experience selling benefits, healthcare, or SaaS solutions specifically to labor and trust clients
• Proven track record of closing 6-figure+ enterprise deals
• Deep understanding of union benefit structures, trust governance, and decision-making processes
• Proficiency in using Salesforce to manage deals and follow-ups
• Ability to travel approximately 30%

Preferred Qualifications

• Familiarity with the digital health space and current industry trends
• Experience managing cross-functional projects in a fast-paced startup environment
• Strong ability to distill complex information into compelling messaging for diverse audiences

Benefits

• Competitive healthcare benefits
• Generous equity compensation
• Unlimited vacation
• Membership in the First Round Network

About the Company

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 to help reach patients earlier and deliver personalized care throughout their journey.