# Labor & Trust Account Executive

**Company:** [Pomelo Care](https://hotfix.jobs/companies/pomelo-care)
**Location:** Remote
**Role:** Account Executive
**Salary:** $340k – $400k/yr
**Experience:** 8+ years
**Skills:** Salesforce, Consultative Selling, Enterprise Sales, Union Benefits, Healthcare Sales, SaaS Sales, Sales Pipeline Management, Quota Attainment, Cross-Functional Collaboration, Presentation Skills
**Posted:** 2026-01-16

> Full-cycle sales executive driving new business with labor trusts, trustees, and union leaders to deliver virtual maternal and pediatric care. Requires 8+ years sales experience, including 5+ in benefits/healthcare/SaaS to labor clients, with proven quota attainment and 6-figure deal closures.

## Job Description

## 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).

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