Labor & Trust Account Executive

Responsibilities

• 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%).

Requirements

• 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.

Compensation

On-target earnings: $340,000-$400,000 per year (includes equity and cash options).