Role Description

Your North Star: Optimizing performance to drive patient enrollment and engagement.

We’re looking for a Head of Outreach & Engagement to lead our Outreach & Engagement team, a critical part of Pomelo’s patient enrollment and engagement engine. In this role, you’ll oversee a growing team of outreach managers and specialists, and be responsible for driving enrollment, activation, and engagement KPIs.

You’ll rigorously and continuously measure team performance to prioritize and oversee the development and implementation of effective, scalable outreach strategies. This is a high-impact leadership position that requires strong people management skills, strategic operational execution, and a deep understanding of call center best practices.

Responsibilities:

• Lead, scale, and inspire Pomelo’s Outreach & Engagement team, including outreach managers and a growing team of specialists, to consistently meet and exceed call performance, enrollment, and activation KPIs.
• Continuously improve performance by analyzing outreach performance data (both qualitative and quantitative) to uncover trends, optimize and prioritize workflow enhancements, and improve key metrics such as enrollment rate and CAC (customer acquisition cost).
• Hire and retain a high performing team that consistently exceeds performance targets while fostering strong team culture, professional development, and inclusivity.
• Oversee coaching, onboarding, and training programs that ensure new and existing team members are set up for success in driving patient engagement and high-quality interactions.
• Prioritize scalable systems and processes to improve the effectiveness of both inbound and outbound outreach efforts.
• Uphold compliance with government regulations and internal policies for all outreach activities, and partner closely with legal and compliance teams as needed.
• Collaborate cross-functionally with Growth, Clinical, Product, and Operations teams to align goals, optimize processes, and drive high-quality patient enrollment and activation.

Who you are:

• 8–10+ years of experience in call center operations or leadership, healthcare operations, or patient engagement, with a strong focus on outbound calling and proactive outreach.
• 7+ years of people management experience, including overseeing managers or team leads in a metric-driven environment.
• Proven track record of using data to drive call center and operational performance improvements and efficiencies.
• Deep understanding of healthcare regulations, Medicaid policies, and value-based care models.
• Strong communication, collaboration, and leadership skills; able to thrive in a fast-paced, evolving startup environment.
• Proficient in healthcare software systems, CRM tools, and telephony platforms
• Passion for improving maternal and infant health outcomes and aligning with Pomelo’s mission.

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.