Cayaba Care

Chief Operating Officer

Cayaba Care

full-time

Posted on:

Location Type: Remote

Location: District of Columbia • Maryland • United States

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Job Level

Lead

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