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Chief Operating Officer

Remote

About Us:
The United States has the poorest maternal and birth outcomes of all developed countries with underserved, Black, Brown, Indigenous communities disproportionately affected. Cayaba Care is working to drastically improve the experience of affected communities by reimagining how we deliver meaningful and compassionate care to expectant moms.

Cayaba Care's mission is to improve pregnancy, birth and the postpartum journey for women and their families by reimagining how maternity care is delivered. Our team is focused on building trust-based engagement and wrap-around support for expectant moms at home, in person and virtually, to ensure they have all the social support they need for a successful and joyful pregnancy journey. We leverage technology to support our virtual engagement that allows us to meet all our moms where they are.

We ensure that our members do not feel alone during their pregnancy journey, and that they have a trusted resource for support, resources, and information throughout their pregnancy, delivery and well into postpartum. Cayaba Care does not replace the primary obstetrician or doctor’s relationships. Instead, we support expectant mothers with all other support services that are traditionally not available through their doctors’ offices.

Our Values:

  • Empathy is at the heart of everything we do. We must always center the experiences of the mothers and families we serve, as well as support and uplift one another.
  • Collaboration is what makes us stronger. We achieve the greatest impact when we work together, share knowledge, and elevate each other’s strengths.
  • Resilience reflects our ability to push through challenges, adapt in a fast-changing environment, and remain committed to our mission no matter the obstacles.

The Role:

Cayaba Care is seeking a Chief Operating Officer (COO)  to serve as the CEO’s primary operating partner and own day-to-day execution across the business. The COO will install a rigorous operating cadence, clarify accountability, and build scalable operational infrastructure to support multi-market expansion and performance excellence. This role will report directly to the CEO. 

This leader will drive execution of 2026 priorities, including scaling operations across Tennessee, Maryland, and Washington, DC and beyond, while improving delivery consistency, implementation speed, and measurable outcomes reporting. This role will directly manage the Care Operations and Care Delivery teams. Other key partners include the Marketing and Membership Acquisition team, Product, Engineering, and Data teams, Finance team, and People team. 

As the Chief Operating Officer, you will serve as the architect of our next phase of growth. You will build the scalable "operating system" and execution engine necessary for multi-market expansion while directly influencing maternal health outcomes. Reporting to the CEO, you will be a core strategic partner in shaping our organizational culture, building high-performing teams, and institutionalizing our mission-driven, community-oriented model.

Responsibilities:

Owning the Operating System (cadence, KPIs, accountability)

  • 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

Care Delivery & Implementation Excellence (time-to-revenue, readiness, repeatability)

  • 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)
  • Build a scalable implementation function (or strengthen it) as contract volume and complexity increase
  • Partner with Product and Technology to maintain operational excellence

Scale Multi-Market Operations & Delivery

  • Lead execution of market scaling, ensuring operational readiness and consistent performance
  • Implement disciplined capacity planning to support rapid growth while protecting care quality and member experience
  • Standardize playbooks and operating procedures across markets; ensure learnings are codified and reused

Customer Success, Renewals & Outcomes/ROI Reporting

  • Strengthen the operating backbone for payer reporting and customer success, improving renewal and expansion performance
  • Partner with analytics and product to advance outcomes reporting and ROI narratives that matter to plans (quality, utilization, cost impact)
  • Create consistent executive-level client performance reviews and action plans

Field Org Design, Leadership Development & Culture

  • Partner with HR to clarify field/market operating org structure, decision rights, and accountability across teams; remove bottlenecks and overlapping ownership
  • Hire, coach, and develop an operations leadership bench; build a high-performance, low-ego execution culture
  • Lead change management and communication practices that improve alignment and reduce organizational drag

Operating Plan & Resource Stewardship with Finance

  • Partner with Finance on annual plan, staffing and capacity models, and unit economics; ensure the operating plan is executable
  • Drive operational efficiency and cost discipline while maintaining quality and member experience
  • Build systems for forecasting, scenario planning, and resource reallocation as conditions change

Professional Qualifications:

  • 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

Personal Attributes:

  • High integrity and empathic approach to leadership and management
  • Mission-driven and values-aligned; committed to improving maternal outcomes and member experience
  • Low-ego, high-ownership operator who drives clarity and execution without creating friction
  • Agile, structured, decisive, and calm under pressure; excellent written and verbal communicator
  • Builder mindset: enjoys creating systems, playbooks, and teams in an ambiguous, fast-changing environment

Why join us:

Working with us is a chance to build something from the ground up, shape the future of maternal health, and grow with a team that values impact, ownership, and care. As an early team member, you’ll help define how we deliver care and support at scale. 

At Cayaba Care, we recognize that great talent deserves great rewards. The expected base salary for this position is between $275,000–$300,000 per year, based on years of relevant experience.

For full-time employees, we offer a comprehensive benefits package designed to support you both professionally and personally:

Time Off That Works for You

  • Recharge with annual paid holidays off.
  • 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.

Comprehensive Health & Wellness Coverage

  • 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.

Security & Future Planning Options

  • 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.

We’re building something great and want you to be part of it. If you're looking for a fast-paced, dynamic environment where your contributions make an impact, apply today!

Please note that our recruitment team will only contact candidates via an official company email address ending in @cayabacare.com. Be cautious of scams; Cayaba Care will never ask for financial information or payments at any stage of the hiring process.

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