Cayaba Care

Chief Operating Officer

Cayaba Care

full-time

Posted on:

Location Type: Remote

Location: District of ColumbiaMarylandUnited States

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About the role

  • Establish quarterly goal setting, KPI ownership, and a consistent execution rhythm (weekly business reviews, SLT check-ins, escalation paths).
  • Build and maintain dashboards that connect enrollment and engagement to capacity, delivery performance, client reporting, and renewals.
  • Drive “on-track / at-risk” management routines with rapid issue resolution and clear decision rights.
  • Operationalize a repeatable delivery and implementation playbook that reduces time-to-revenue and improves launch predictability.
  • Ensure cross-functional readiness for new plan and market launches (staffing, training, tooling, reporting, compliance).
  • Lead execution of market scaling, ensuring operational readiness and consistent performance.
  • Strengthen the operating backbone for payer reporting and customer success, improving renewal and expansion performance.
  • Partner with HR to clarify field/market operating org structure, decision rights, and accountability across teams; remove bottlenecks and overlapping ownership.
  • Partner with Finance on annual plan, staffing and capacity models, and unit economics; ensure the operating plan is executable.

Requirements

  • A track record of senior operations leadership, ideally in early-stage tech-enabled healthcare services or similarly complex, human-delivered services.
  • Demonstrated success installing operating cadence, KPI systems, and cross-functional execution discipline in a scaling organization.
  • Robust experience scaling multi-site or multi-market operations while maintaining quality and customer satisfaction.
  • Strong people leadership and organizational design capability; experience building leaders and clarifying accountability.
  • Comfort partnering deeply with product, data, and engineering teams to operationalize tooling and reporting improvements.
Benefits
  • Salaried (Exempt) Employees: Enjoy unlimited time off after the 90-day probation period.
  • Full-Time (Non-exempt) Employees: Receive three weeks of paid time off after the 90-day probation period.
  • Medical Insurance: Access top-tier healthcare, covering hospital, surgical, and prescription drug benefits. Coverage begins the first of the following month.
  • Dental Insurance: Coverage for preventive care, as well as basic and major procedures.
  • Vision Insurance: Coverage for routine eye exams and eyeglasses.
  • Life Insurance: Financial protection for your beneficiaries.
  • Disability Insurance: Short-term and long-term coverage in case of illness or injury.
  • 401(k) Retirement Plan: Opportunity to save for the future.

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard skills
KPI ownershipdashboard buildingissue resolutiondelivery and implementation playbookoperational readinessmarket scalingpayer reportingcapacity modelsunit economics
Soft skills
senior operations leadershipcross-functional execution disciplinepeople leadershiporganizational designaccountability clarification