Chief of Staff

Catena

. Manage the COO’s calendar across internal operations, board meetings, and client travel to Puerto Rico .

Posted 11/5/2026full-timeRemote • Dominican Republic, Colombia, Brazil, Peru, Mexico, ArgentinaLeadWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in executive calendar management, client coordination, and compliance tracking within regulated industries. Proficient in building operational systems and documentation to enhance organizational efficiency.

Highest-signal resume keywords

Executive Calendar ManagementClient CoordinationCompliance TrackingBilingual Communication (Spanish & English)Operational System Development

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Microsoft OutlookMicrosoft ExcelSmartsheetSOP DevelopmentInvoice ReconciliationProject Management ToolsRegulatory ComplianceData TrackingWorkflow DocumentationBilingual Communication

Soft Skills

Organizational SkillsCommunication SkillsProblem-SolvingCollaborationAttention to Detail

Tools & Technologies

SmartsheetAsanaClickUpNotionTodoist

Industry Keywords

Medicare AdvantageHealthcareRegulated IndustryCompliance FilingsVC-Backed Startup

About the role

Key responsibilities & impact

Manage the COO’s calendar across internal operations, board meetings, and client travel to Puerto Rico
Triage the COO’s Outlook inbox and draft responses on his behalf
Coordinate board meeting logistics, member communications, and follow-up actions
Build and run a follow-up tracking system for open action items across the leadership team
Act as the day-to-day operational contact for a Medicare Advantage health plan client in Puerto Rico
Reconcile invoices, coordinate billing, and complete client compliance attestations
Schedule and coordinate meetings with the client’s administrative team in Spanish
Support the COO during client visits with coordination and translation
File recurring state-by-state regulatory forms on a monthly cycle
Track compliance deadlines across multiple states and ensure on-time submission
Write SOPs for each recurring regulatory process
Coordinate with internal teams to collect compliance documentation
Set up project and task tracking in Smartsheet or a comparable tool to replace email- and text-based workflows
Document processes and build operational playbooks as headcount grows past 160
Identify bottlenecks and recommend tools or automations to remove them
Coordinate onboarding logistics for new hires during the hiring ramp

Requirements

What you’ll need

4+ years of professional experience, including 2+ years as a Chief of Staff, Executive Assistant to a C-suite executive, or Executive Operations Manager
Experience at a VC- or PE-backed startup or scale-up (30–200 employees)
Hands-on use of Microsoft Outlook for executive calendar and inbox management
Hands-on use of Microsoft Excel for reporting and tracking, including pivot tables, trackers, and reconciliations
Experience building and maintaining trackers in Smartsheet or a comparable PM tool such as Asana, ClickUp, or Notion
At least one SOP, tracking system, or workflow built from scratch and documented on CV
Client-facing coordination experience covering scheduling, billing, or invoice reconciliation with external stakeholders
Native or C1+ Spanish and C1+ English (CEFR)
Nice to have: experience in healthcare, Medicare Advantage, health plans, or another regulated industry
Nice to have: experience with recurring regulatory or compliance filings and deadline tracking
Nice to have: daily use of Todoist or AI productivity tools
Nice to have: experience tracking account P&L or building financial data visualizations
Nice to have: consulting or business school background with hands-on execution experience

Benefits

Comp & perks

Competitive Salary: Based on experience and skills
Remote Work: Fully remote—work from anywhere
Team Incentives: Recognition for maintaining 100% CRM hygiene and on-time reporting
Generous PTO: In accordance with company policy
Health Coverage for PH-based talents: HMO coverage after 3 months for full-time employees
Direct Mentorship: Guidance from international industry experts
Learning & Development: Ongoing access to resources for professional growth
Global Networking: Connect with professionals worldwide