About the role
Job Application for Labor & Trust Account Executive at Pomelo Care Labor & Trust Account Executive United States Apply About us At Pomelo Care, we are redefining the healthcare journey for women and children. As the leading virtual medical practice in our field, we provide a continuous circle of support—from the first steps of family building and the complexities of pregnancy to the nuances of postpartum, pediatric, and midlife care. We aren't just a clinic; we are a multidisciplinary engine of clinicians, engineers, and problem-solvers dedicated to closing the gaps in traditional care. By leveraging a high-touch, technology-driven platform, we identify risks early and deliver deeply personalized, 24/7 virtual care. We are here to prove that better data and patient-centered care lead to better outcomes, raising the standard of care for families nationwide. Role Responsibilities 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. As a Labor & Trust Account Executive at Pomelo, you will: 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%) What you'll do 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. Why you should join our team By joining Pomelo, you will get in on the ground floor of a fast-moving, well-funded, and mission-driven startup where you will have a profound impact on the patients we serve. And you'll learn, grow, be challenged, and have fun with your team while doing it. We strive to create an environment where employees from all backgrounds are respected. We value working across disciplines, moving fast, data-driven decision making, learning, and always putting the patient first. We also 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) At Pomelo, we are committed to hiring the best team to improve outcomes for all mothers and babies, regardless of their background. We need diverse perspectives to reflect the diversity of problems we face and the population we serve. We look to hire people from a variety of backgrounds, including but not limited to race, age, sexual orientation, gender identity and expression, national origin, religion, disability, and veteran status. Our salary ranges are based on paying competitively for our company’s size and industry, and are one part of the total compensation package that also includes equity, benefits, and other opportunities at Pomelo Care. In accordance with New York City, Colorado, California, and other applicable laws, Pomelo Care is required to provide a reasonable estimate of the compensation range for this role. Individual pay decisions are ultimately based on a number of factors, including qualifications for the role, experience level, skillset, geography, and balancing internal equity. On-target earnings for this role are expected to range from $340,000-$400,000 per year. We expect most candidates to fall in the middle of the range. We also believe that your personal needs and preferences should be taken into consideration, so we allow some choice between equity and cash. Potential Fraud Warning Please be cautious of potential recruitment fraud. With the increase of remote work and digital hiring, phishing and job scams are on the rise with malicious actors impersonating real employees and sending fake job offers in an effort to collect personal or financial information. Pomelo Care will never ask you to pay a fee or download software as part of the interview process with our company. Pomelo Care will also never ask for your personal banking or other financial information until after you have signed an offer of employment and completed onboarding paperwork that is provided by our People Operations team. All official communication with Pomelo Care People Operations team will come from domain email addresses ending in @pomelocare.com. If you receive a message that seems suspicious, we encourage you to pause communication and contact us directly at to confirm its legitimacy. For your safety, we also recommend applying only through our official Careers page. If you believe you have been the victim of a scam or identity theft, please contact your local law enforcement agency or another trusted authority for guidance. Create a Job Alert Interested in building your career at Pomelo Care? Get future opportunities sent straight to your email. Create alert Apply for this job * indicates a required field Autofill with MyGreenhouse First Name * Last Name * Email * Phone Country Phone Resume/CV * Attach Attach Dropbox Google Drive Enter manually Enter manually Accepted file types: pdf, doc, docx, txt, rtf Do you currently reside in the US? * Select... Are you authorized to work in the US? * Select... Will you require sponsorship to work now or in the future? * Select... How did you hear about us? * Linkedin Indeed Employee Referral Google Search Other Job Board Social Media How many years of experience do you have selling directly to Trustees, Benefits Leaders or Union Leadership? * Have you owned the full sales cycle (from prospecting to closing and contracting) and if so, how many deals have you closed? * Have you sold a solution for which there were several competitors? * In your last role, what was your annual quota? What was your quota attainment in that last period? What was your average quota attainment over your entire tenure in that role? * Please note: Responses will be verified via reference or documentation. Which state do you reside in? * Select... Voluntary Self-Identification For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file. As set forth in Pomelo Care’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law. Gender Select... Are you Hispanic/Latino? Select... Race & Ethnicity Definitions If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. 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Disabilities include, but are not limited to: Alcohol or other substance use disorder (not currently using drugs illegally) Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS Blind or low vision Cancer (past or present) Cardiovascular or heart disease Celiac disease Cerebral palsy Deaf or serious difficulty hearing Diabetes Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders Epilepsy or other seizure disorder Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome Intellectual or developmental disability Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD Missing limbs or partially missing limbs Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS) Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities Partial or complete paralysis (any cause) Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema Short stature (dwarfism) Traumatic brain injury Disability Status Select... 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