Remote Chief of Staff (Healthcare)

Location: Remote, anywhere in LATAM; listed locations include Honduras, the Dominican Republic, Argentina, Colombia, Brazil, Peru, and Mexico. Full-time work requires overlap with US Eastern business hours, including early mornings and occasional weekend availability.

Company

hirify.global connects experienced candidates with startups and scale-ups backed by leading US and EU investors. The client is a PE-backed health technology company serving Medicare Advantage plans and risk-bearing providers, operating across the United States and Puerto Rico.

What you will do

• Manage the COO’s calendar, Outlook inbox, board meeting logistics, travel coordination, follow-ups, and leadership action-item tracking.
• Coordinate day-to-day operations for a Medicare Advantage client in Puerto Rico, including scheduling, billing, invoice reconciliation, compliance attestations, client visits, and translation.
• File recurring state regulatory forms, track compliance deadlines, collect documentation, and coordinate monthly submissions.
• Build project and task tracking in Smartsheet or a comparable tool to replace email- and text-based workflows.
• Document processes, create SOPs and operational playbooks, identify bottlenecks, recommend tools or automations, and coordinate onboarding logistics during rapid growth.

Requirements

• 4+ years of professional experience, including 2+ years as a Chief of Staff, C-suite Executive Assistant, or Executive Operations Manager.
• Experience at a VC- or PE-backed startup or scale-up with 30–200 employees.
• Hands-on experience with Microsoft Outlook for executive calendar and inbox management and Microsoft Excel for pivot tables, trackers, reporting, and reconciliations.
• Experience building and maintaining trackers in Smartsheet or a comparable project-management tool such as Asana, ClickUp, or Notion.
• At least one SOP, tracking system, or workflow built from scratch and documented on the CV.
• Client-facing coordination experience involving scheduling, billing, or invoice reconciliation with external stakeholders.
• Native or C1+ Spanish and C1+ English according to CEFR.

Nice to have

• Experience in healthcare, Medicare Advantage, health plans, fintech, insurtech, or another regulated industry.
• Experience with recurring regulatory or compliance filings and deadline tracking.
• Daily use of Todoist or AI productivity tools.
• Experience tracking account P&L or building financial data visualizations.
• Consulting or business school background with hands-on execution experience.

Culture & Benefits

• Fully remote work from anywhere in LATAM with US Eastern business-hours overlap.
• Competitive salary based on experience and skills, generous PTO, and ongoing learning and development resources.
• HMO coverage after three months for full-time employees who are based in the Philippines.
• Direct mentorship from international industry experts and global networking opportunities.
• Recognition for maintaining 100% CRM hygiene and completing reporting on time.

Hiring process

• Application, screening, skills assessment, topgrading interview, client interview, job offer, and client onboarding.