[Hiring] Chief of Staff @Pearl

Role Description

The role starts as roughly 80% executive administration and 20% operations:

• Managing the COO’s schedule and inbox
• Coordinating board logistics
• Handling billing and compliance work for a Medicare Advantage client in Puerto Rico
• Running monthly state regulatory filings

As trust builds, the role moves toward a 50/50 split and a strategic operations partnership. Success means the COO can hand off follow-ups and decisions with confidence, and clear systems replace ad-hoc workflows.

Core Responsibilities

• Executive Administration & Calendar Management
  • 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
• Client Account Coordination
  • 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
• Regulatory & Compliance Coordination
  • 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
• Operations & Systems
  • 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

Qualifications

• 4+ years of professional experience
• 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
• Experience with Microsoft Excel for reporting and tracking (pivot tables, trackers, reconciliations)
• Experience building and maintaining trackers in Smartsheet or a comparable PM tool (Asana, ClickUp, Notion)
• At least one SOP, tracking system, or workflow built from scratch, 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 (fintech, insurtech)
• 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

Benefits

• 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

Our Recruitment Process

• Application
• Screening
• Skills Assessment
• Topgrading Interview
• Client Interview
• Job Offer
• Client Onboarding

Ready to Join Us?

If you’re empathetic, organized, and passionate about improving patient experiences through operational excellence, this role is for you. Apply now to help make specialized healthcare more accessible to patients across the U.S.