Chief of Staff

This is a fully remote position, open to applicants in Dominican Republic, +5 more countries.

📋 Description

• Oversee the COO's calendar, managing internal operations, board meetings, and client travel arrangements to Puerto Rico.

• Prioritize the COO's Outlook inbox and compose replies on his behalf.

• Organize logistics for board meetings, including member communications and follow-up tasks.

• Develop and maintain a tracking system for open action items involving the leadership team.

• Serve as the primary operational contact for a Medicare Advantage health plan client in Puerto Rico.

• Reconcile invoices, manage billing, and complete compliance attestations for clients.

• Arrange and facilitate meetings with the client’s administrative team in Spanish.

• Assist the COO during client visits through coordination and translation support.

• File recurring regulatory forms on a monthly basis for various states.

• Monitor compliance deadlines across multiple states to ensure timely submissions.

• Draft Standard Operating Procedures (SOPs) for each recurring regulatory process.

• Collaborate with internal teams to gather compliance documentation.

• Implement project and task tracking using Smartsheet or a similar tool to replace email- and text-based workflows.

• Document processes and create operational playbooks as the team expands beyond 160 employees.

• Identify workflow bottlenecks and suggest tools or automations to alleviate them.

• Organize onboarding logistics for new hires during hiring surges.

⛳️ Requirements

• A minimum of 4 years of professional experience, including at least 2 years in a role such as Chief of Staff, Executive Assistant to a C-suite executive, or Executive Operations Manager.

• Experience working in a VC- or PE-backed startup or scale-up environment (30–200 employees).

• Proficient in Microsoft Outlook for managing executive calendars and inboxes.

• Skilled in Microsoft Excel for reporting and tracking purposes, including the use of pivot tables, trackers, and reconciliations.

• Proficient in building and maintaining trackers in Smartsheet or a comparable project management tool like Asana, ClickUp, or Notion.

• Experience creating at least one SOP, tracking system, or workflow from scratch, documented on your CV.

• Client-facing coordination experience, specifically in scheduling, billing, or invoice reconciliation with external partners.

• Native or C1+ proficiency in Spanish and C1+ proficiency in English (CEFR).

• Preferred: experience in healthcare, Medicare Advantage, health plans, or other regulated industries.

• Preferred: familiarity with recurring regulatory or compliance filings and tracking deadlines.

• Preferred: daily use of Todoist or AI productivity tools.

• Preferred: experience with account P&L tracking or financial data visualization.

• Preferred: background in consulting or business school with practical execution experience.

🏝️ Benefits

• Competitive Salary: Based on experience and skills.

• Remote Work: Fully remote—work from anywhere.

• Team Incentives: Recognition for maintaining 100% CRM hygiene and timely 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.