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Labor & Trust Account Executive

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Pomelo Care

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Location:
United States

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Category:
Sales

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Contract Type:
Not provided

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Salary:

340000.00 - 400000.00 USD / Year
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Job Description:

Pomelo is looking for an exceptional and experienced founding Labor & Trust Account Executive. 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.

Job Responsibility:

  • 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
  • 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
What we 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)

Additional Information:

Job Posted:
January 20, 2026

Employment Type:
Fulltime
Work Type:
Remote work
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