# Remote Chief of Staff & Executive Assistant

> Pearl · Caracas, Venezuela, Bolivarian Republic of (Remote) · Full-time · Posted 2026-06-03

**Workplace:** remote

**Department:** Administration and Executive Assistance

## Description

**Work From Anywhere in LATAM or the Philippines**

**Work Schedule:** EST | Full-time, aligned with US East Coast business hours (40 hours per week, Monday–Friday)

**Compensation Range:** $2,000.00USD/month based on experience

An early-stage, founder-led company in the healthcare and consumer space is building data-driven outreach and operations, looking for a Chief of Staff & Executive Assistant to protect founder focus time and own both executive support and research operations end-to-end.

The business is run by two founders in a lean, fast-moving remote setup where a single trusted hire moves fluidly between high-trust administrative work and hands-on market research — no layers of process, just direct ownership.

Day-to-day, the role manages both founders' inboxes and calendars, coordinates meetings and travel, tracks expenses and vendor invoices, and maintains shared documentation, while dedicating roughly half the week to building research spreadsheets, sourcing verified contact data, and queuing outreach. Success means founders stay focused on high-leverage work while a reliable system handles scheduling, logistics, and a steadily growing, well-organized research pipeline.

## Requirements

**Must-Have**

-   3+ years of executive assistant or executive support experience for founders or C-level leaders in a remote environment
-   Hands-on management of executive inboxes and calendars across multiple stakeholders and time zones, including scheduling and conflict resolution
-   Strong proficiency in Google Workspace (Google Sheets, Gmail, Google Drive, Google Calendar)
-   Demonstrated experience building and maintaining research or contact databases at scale (e.g., verified contact directories, structured data sets)
-   Experience coordinating travel, expense tracking, reimbursements, and vendor/invoice processing
-   Working use of AI tools (Claude or ChatGPT) for day-to-day research and drafting tasks
-   C1+ English (CEFR) for founder- and client-facing written and verbal communication

**Nice-to-Have**

-   Prior experience supporting founders or C-level leaders at an early-stage or fast-paced startup
-   Background in healthcare, consumer, or B2C environments
-   Familiarity with lightweight CRM tools or Google Sheets–based outreach workflows
-   Experience queuing or managing outbound and lead-generation workflows
-   Light project management across multiple operational workstreams

**About Pearl Talent**

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. They're looking for the sharpest, hungriest candidates who they can consistently promote and work with over many years. Candidates we've hired have been flown out to the US and EU to work with their clients, and even promoted to roles that match folks onshore in the US.

Hear why we exist, what we believe in, and who we're building for: Watch here: [https://www.loom.com/share/863b8e426e6d48309aa8f4ea4c1c94cd](https://www.loom.com/share/863b8e426e6d48309aa8f4ea4c1c94cd)

## 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**

1.  Application
2.  Screening
3.  Skills Assessment
4.  Topgrading Interview
5.  Client Interview
6.  Job Offer
7.  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.

## Apply

[Apply at Pearl](https://apply.workable.com/pearltalent/j/844F37566A/apply)

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