Remote Chief of Staff

Work From Anywhere in LATAM

Work Schedule:

EST | Full-time with US Eastern business hours overlap, including early mornings and occasional weekend availability

About the company

Pearl works with the top 1% of candidates from around the world and connects them with the best startups in the US and EU. Our clients have raised over $5B in aggregate and are backed by companies like OpenAI, a16z, and Founders Fund.

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About the ClientA technology-driven healthcare company that helps organizations streamline operations and improve efficiency is looking for a Chief of Staff to work directly with the Chief Operating Officer and keep executive priorities moving.

The company is scaling, and the COO needs a hands‑on partner to bring structure to executive workflows, project tracking, and reporting as the business grows.

About the Role Day-to-day, the Chief of Staff manages the COO’s calendar and Outlook inbox, tracks commitments and deadlines, coordinates cross‑functional projects, and supports administrative work for key client accounts, including billing documentation and compliance attestations. The role starts hands‑on and expands into greater ownership of operational initiatives over time. Success at 90 days means independently running recurring administrative work, keeping critical deadlines visible, and making decisions without constant direction.

• Manage the COO’s calendar, meetings, and competing priorities
• Run Outlook inbox management and executive follow‑ups
• Track key commitments, deadlines, and action items
• Set up task‑management systems that improve executive productivity

• Coordinate stakeholders, timelines, and deliverables across business functions
• Maintain project trackers, operational dashboards, and reports in Smartsheet and Excel
• Support administrative processes for corporate operations, compliance, and internal functions
• Identify inefficiencies and recommend process improvements

• Support administrative and operational work for key client accounts
• Coordinate billing documentation, compliance attestations, and recurring client requests
• Communicate with internal and external stakeholders in English and Spanish
• Track outstanding client deliverables and support account performance reporting

• Prepare clear updates on project status, priorities, and business performance
• Organize and visualize operational and financial data for leadership decisions
  
  Identify where AI, automation, and productivity tools can save time
• Take on ownership of operational initiatives as the role grows

• 4+ years of experience in executive support, project management, business operations, consulting, or a similar execution-focused role
• Hands‑on use of Microsoft Outlook for executive calendar and inbox management
• Microsoft Excel for reporting and tracking (pivot tables, dashboards, data organization)
• Experience building and maintaining project trackers or dashboards in Smartsheet
• Experience coordinating cross‑functional projects with multiple stakeholders, timelines, and deliverables
• At least one task‑management, tracking, or process system built or improved, documented on CV
• C1+ English and C1+ Spanish (CEFR)

• Prior experience as a Chief of Staff or direct operational partner to a C‑suite executive
• Experience in healthcare, health technology, or another regulated industry
• Background in management consulting, business operations, or operational transformation
• Experience with Todoist and AI‑enabled productivity tools
• Experience supporting distributed teams or fast‑growing organizations

• 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

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