RVP, Labor, Trust and Public Sector Partnerships

About the role

You will own the end-to-end sales strategy for Labor, Trust, and Public Sector partnerships, acting as the primary external advocate for Pomelo's mission within the benefits and labor ecosystem. This role requires you to bring 24/7 virtual maternal, pediatric, and midlife care to working families by securing enterprise-level commitments that expand access to our solutions. You will be the voice of the customer internally, translating trustee, benefits manager, and union feedback into product and positioning improvements. Your work will directly influence Pomelo's revenue trajectory while advancing health equity for underrepresented populations. You will build and maintain credible relationships based on expertise, integrity, and a shared commitment to patient-first outcomes. This position is designed for a leader who thrives on ownership, ambiguity, and the ability to shape long-term partnerships from initial contact through multi-year contract execution. You will be measured not only on closed deals but also on the strength of the strategic relationships you cultivate and the trust you establish across complex buying organizations.

Key facts

What you'll do

Champion Pomelo's mission with enthusiasm and credibility, utilizing relationship building to drive market demand across labor, trust, and public sector audiences.

Manage the entire sales cycle for Labor & Trust opportunities, from pipeline generation through contract close, ensuring disciplined execution and rigorous forecasting.

Partner with BDR to source and close new opportunities, aligning marketing intent with enterprise selling realities.

Lead consultative sales conversations with trustees and benefits managers, uncovering needs, aligning on outcomes, and tailoring Pomelo's value proposition to stakeholder priorities.

Assess and engage decision-makers, influencers, and champions, crafting persona-specific strategies to deliver value in every interaction and advance deals through complex committees.

Develop a detailed plan for meeting your individual sales targets, including activity metrics, account strategies, and stakeholder mapping.

Consistently meet and exceed sales targets by focusing on strategic, high-value accounts and prioritizing opportunities with the greatest impact on mission and revenue.

Represent Pomelo at labor conferences, trustee summits, and industry events, investing travel time to build visibility and credibility in key markets.

Coordinate cross-functional collaboration with product, clinical, and customer success teams to ensure seamless onboarding and long-term retention of new trust and labor partnerships.

Maintain precise deal tracking and forecasting in Salesforce, ensuring accurate pipeline management and reliable reporting to leadership.

Build narrative-driven presentations and proposals that clearly communicate outcomes, ROI, and the patient impact of Pomelo's solutions.

Develop and execute account plans for priority trusts and labor organizations, incorporating research, stakeholder analysis, and competitive intelligence.

Act as a subject matter expert on union benefit structures, trust governance, and decision-making processes, positioning Pomelo as a trusted advisor rather than a vendor.

Continuously refine sales playbooks based on feedback, results, and evolving market dynamics to improve conversion rates and cycle times.

Requirements

Bring 8+ years of direct sales experience with a strong track record of quota attainment, including at least 5 years selling benefits, healthcare, or SaaS solutions to labor and trust clients.

Demonstrate a deep understanding of union benefit structures, trust governance, and decision-making processes within public and nonprofit sectors.

Show a proven track record of closing 6-figure+ enterprise deals and consistently achieving or exceeding quota in previous roles.

Display the ability to lead complex end-to-end sales processes, with exceptional organizational skills and proficiency in using tools like Salesforce to manage deals, forecast, and follow-ups.

Exhibit strong written, verbal, and presentation abilities, capable of distilling complex information into clear, compelling messaging for diverse audiences, including executive leadership and union representatives.

Operate as an adaptive, pragmatic professional who thrives in a fast-paced, metric-driven startup environment with competing priorities and shifting timelines.

Pursue familiarity with the healthcare system and the digital health space, including industry and competitive trends, and demonstrate a willingness to research and rapidly learn new domains.

Leverage experience managing cross-functional projects, solving problems across teams, and turning abstract ideas into actionable strategies that drive measurable outcomes.

Embody a mindset focused on continuous improvement and a relentless drive for success, balancing ambition with integrity and a commitment to patient-first values.

Practical notes

This role requires travel approximately 30% of the time to attend labor conferences, trustee summits, and industry events across the United States. The position is full-time and open to candidates located in the continental US, with flexibility for remote work in compliance with company policies. Compensation details, including base salary, variable pay, and equity, are outlined in the key facts section and may vary based on experience, skills, and certifications. No additional benefits or perks are described beyond those stated in the compensation and eligibility requirements.