Head of Outreach & Engagement

United States

About us

Pomelo Care is a multi-disciplinary team of clinicians, engineers and problem solvers who are passionate about improving care for moms and babies. We are transforming outcomes for pregnant people and babies with evidence-based pregnancy and newborn care at scale. Our technology-driven care platform enables us to engage patients early, conduct individualized risk assessments for poor pregnancy outcomes, and deliver coordinated, personalized virtual care throughout pregnancy, NICU stays, and the first postpartum year. We measure ourselves by reductions in preterm births, NICU admissions, c-sections and maternal mortality; we improve outcomes and reduce healthcare spend.

Role Description

We are hiring for an innovative, data-driven Head of Outreach & Engagement to drive revenue through scaleable, tech-forward solutions. Reporting into the VP of Marketing, you will be responsible for developing and motivating a team of Outreach Managers and Specialists responsible for hitting business-critical enrollment, activation, and engagement KPIs. This is a high-impact leadership position that requires a strong focus on strategic outcomes. 

What you’ll do

  • Drive outcomes that scale by pulling all available levers to ensure revenue-driving enrollment & activation targets are met or exceeded every month.
  • Partner with cross-functional teams to identify new use cases for telephonic outreach, tooling and strategies that enable outreach to drive additional revenue and increase LTV.
  • Accountable for the Outreach P&L, along with CAC and LTV to CAC ratio, capacity planning, hiring, and retention, including managing a motivating, cost-effective sales compensation strategy.
  • Lead the department’s efforts to efficiently scale by prioritizing the right technology to deliver ROI.
  • Leverage data to drive action. Define effective team KPIs and partner with managers to use KPIs to inform sales scripting, pipeline and outreach strategies, and performance management needs.
  • Develop a high-performing team at scale. Effectively influence cross functional stakeholders to prioritize critical path items for outreach success, level up & invest in our people managers, and ensure thoughtful career paths to promote retention.

What you’ll bring

  • 8+ years of experience in a high-volume sales or outbound engagement environment
  • 5+ years of people leadership experience, including managing managers, in a metric-driven environment.
  • Proven track record of using cutting-edge technology and data to drive operational excellence
  • Strong communication, collaboration, and leadership skills; able to thrive in a fast-paced, evolving startup environment.
  • Proficient inCRM tools, telephony platforms; experience with healthcare software systems a plus.
  • Familiarity with outbound sales in a healthcare or other regulated space. Passion for Pomelo’s mission to improve maternal and infant health outcomes.

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. A reasonable estimate of the current salary range is $185,000-$215,000 plus a bonus. 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 careers@pomelocare.com  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.

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