Remote Chief of Staff

Pearl

3d • Remote

About The Position

Pearl Talent is hiring a remote Chief of Staff to work directly with the COO of a scaling, technology-driven healthcare company. The company helps organizations streamline operations and improve efficiency. The role supports the COO by organizing executive workflows, tracking projects and reporting, coordinating across functions, and assisting with administrative work for key client accounts, including billing documentation and compliance attestations.

The position begins with hands-on executive and administrative support and is expected to expand into greater ownership of operational initiatives. Success within the first 90 days means independently managing recurring administrative work, keeping critical deadlines visible, and making decisions without constant direction. The role is remote and open to candidates anywhere in Latin America, with work aligned to U.S. Eastern business hours and early-morning overlap.

Requirements

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

Nice To Haves

• 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.

Responsibilities

• Manage the COO’s calendar, meetings, and competing priorities.
• Manage the COO’s Outlook inbox 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 ownership of operational initiatives as the role grows.

Benefits

• Competitive salary based on experience and skills.
• Fully remote work from anywhere.
• Team incentives and recognition for maintaining 100% CRM hygiene and on-time reporting.
• Generous PTO in accordance with company policy.
• HMO coverage after 3 months for full-time employees in the Philippines.
• Direct mentorship from international industry experts.
• Ongoing access to learning and development resources.
• Opportunities to connect with professionals worldwide.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed