We are seeking a highly skilled and motivated Outreach & Engagement Supervisor to join our team. As the Outreach & Engagement Supervisor, you play a pivotal role in overseeing and optimizing the daily operations of our Outreach team. This leadership position involves supervising a team of Outreach & Engagement specialists, ensuring adherence to quality standards, achieving our enrollment goals, and driving effective communication with prospective patients. You will  collaborate with the Outreach Manager to develop and implement outreach strategies to enroll  patients in Pomelo and schedule new appointments. You will be responsible for maintaining a positive and efficient work environment, monitoring key performance indicators, and ensuring compliance with healthcare regulations.


  • Monitor and evaluate specialist performance through call monitoring, reporting, and feedback sessions.
  • Oversee the daily operations of direct reports, ensuring that specialists meet performance targets and key performance indicators.
  • Create and maintain team schedules to ensure adequate coverage.
  • Review and approve PTO and timecard submissions.
  • Handle escalated customer inquiries or issues.
  • Monitor call quality and adherence to established protocols and standards by conducting regular audits of call recordings and specialist interactions.
  • Ensure compliance with government regulations and guidelines in all outbound calling and outreach activities.
  • Foster a supportive and inclusive team environment, encouraging team collaborative growth and development.

Who you are

  • Proven experience in a call center supervisory or management role, preferably in a healthcare setting.
  • Supervise a team of outreach specialists providing regular workforce management and coaching interventions to achieve enrollment KPIs.
  • Proficiency in using call center software and CRM systems.
  • Strong knowledge of Medicaid policies, procedures, and outreach strategies.
  • Able to work evenings and weekends, with a standard schedule of 9am-5:30pm PST on weekdays and 8am-4:30pm PST on weekends.
  • Excellent communication and interpersonal skills.
  • Strong analytical and problem-solving abilities.
  • Ability to work collaboratively and lead a team.

Bonus points if you have any of the following

  • Experience working in a fast-paced and dynamic startup environment.
  • Are fluent in speaking and writing Spanish.

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 and flexible vacation policy
  • 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)
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