Labor & Trust Account Executive

Responsibilities

• Champion Pomelo's mission and build relationships that drive market demand.
• Manage the full sales cycle for Labor & Trust opportunities, from pipeline generation through contract close.
• Partner with BDRs to source and close new opportunities.
• Lead consultative sales conversations with trustees and benefits managers, uncovering needs, aligning on outcomes, and tailoring Pomelo's value proposition.
• Assess and engage decision-makers, influencers, and champions using persona-specific strategies.
• Develop detailed plans to meet individual sales targets.
• Meet and exceed sales targets by focusing on strategic, high-value accounts.
• Represent Pomelo at labor conferences, trustee summits, and industry events; travel is approximately 30%.

Requirements

• 8+ years of direct sales experience with a strong record of quota attainment.
• 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 success closing six-figure-plus enterprise deals and consistently achieving quota.
• Experience leading complex, end-to-end sales processes.
• Exceptional organizational skills and proficiency with Salesforce.
• Strong written, verbal, and presentation skills, including the ability to distill complex information into clear messaging for diverse audiences.
• Adaptive, pragmatic, and comfortable in a fast-paced, metric-driven startup environment.
• Familiarity with the healthcare system and digital health space, including industry and competitive trends.
• Experience managing cross-functional projects, solving problems across teams, and turning ideas into actionable strategies.
• Continuous-improvement mindset and strong drive for results.

Benefits and Compensation

• Comprehensive health, dental, and vision coverage for employees and families.
• High-deductible health plans with HSA options.
• Flexible Spending Account (FSA).
• Equity grant participation.
• 401(k) program.
• Competitive vacation policy.
• 16 weeks of paid parental leave.
• Fully remote work flexibility within the US.
• Base salary range: $190,000-$210,000.
• Expected on-target earnings: $380,000-$420,000, plus equity.