Senior Executive Assistant

**Industry**: Startup / Operations / Early-Stage Tech
**Work Arrangement**: Fully Remote (with overlap in U.S. working hours - EST or PST depending on founder availability)

**Job Type**: Independent Contractor, Full-time
**Locations**:

- Philippines
- LATAM (Mexico, Colombia, Argentina, Brazil)
- Other remote regions with strong English communication and startup experience

**About Pearl Talent**:
Hear why we exist, what we believe in, and who we’re building for: WATCH HERE
Why Work with Us?
At Pearl, we’re not just another recruiting firm—we connect you with exceptional opportunities to work alongside visionary US and EU founders. Our focus is on placing you in roles where you can grow, be challenged, and build long-term, meaningful careers.
**About the Company**:
Our client is an AI-powered healthcare advocacy startup on a mission to help patients navigate the U.S. healthcare system with empathy and precision. Combining cutting-edge automation with human-centered support, they help Medicare patients manage care plans, diagnoses, and medical billing while reducing administrative complexity.
This is a fast-moving, high-impact startup backed by industry leaders from healthcare and technology — built on a culture of ownership, humility, and execution.
**About the Company**:
Our client is a rapidly growing early-stage startup operating at the intersection of technology, operations, and strategy. The company is led by mission-driven founders who are scaling fast and need reliable, high-execution operational support. The environment is dynamic, fast-paced, and ideal for someone who thrives in ambiguity and takes ownership from day one.
**Role Overview**:
We’re looking for a Senior Executive Assistant / Chief of Staff to provide operational, administrative, and strategic leverage to the founding team. This role blends high-level coordination, project management, and communication excellence — ensuring that the founders stay focused on strategic growth while daily operations run seamlessly.
**Your Impact**:

- You’ll be the operational engine behind the founders — ensuring their time and focus are spent where it matters most.
- Your structure and foresight will drive organizational efficiency, enabling the company to scale faster and smarter.
- You’ll establish systems, SOPs, and processes that will become the backbone of company operations.
- You’ll enhance founder productivity, communication, and alignment across all internal and external stakeholders.

**Core Responsibilities**:
**Founder Operations & Administrative Support - 40%**:

- Manage the founders’ day-to-day operations, priorities, and workflows.
- Oversee executive calendars, meetings, travel logistics, and partner coordination.
- Maintain and optimize operational infrastructure, including CRMs, shared drives, and productivity tools.
- Act as the primary communication bridge between the founders and internal teams or external stakeholders.

**Recruiting & People Operations - 25%**:

- Maintain organized documentation, HR records, and compliance processes to ensure accessibility and structure.

**Project & Systems Management - 20%**:

- Build and manage internal systems for task tracking, reporting, and documentation.
- Streamline workflows to improve productivity for founders and cross-functional teams.
- Lead ad-hoc strategic projects, including vendor coordination, event planning, and process optimization.

**Communication & Coordination - 15%**:

- Draft professional, concise internal and external communications.
- Anticipate needs across the founders and team; proactively remove blockers to keep initiatives moving.
- Handle sensitive and confidential information with discretion and high professionalism.

**Requirements**:
**Must-Have (required)**:

- 2-3+ years of experience as a Chief of Staff, or Operations Specialist.
- Advanced English communication skills (written and spoken).
- Proficiency in Google Workspace, Slack, and Asana (or similar tools).
- Strong organizational, multitasking, and project management abilities.
- Proven ability to operate independently and adapt to fast-changing priorities.
- Excellent written communication — polished, professional, and concise.
- High level of discretion and judgment in handling confidential matters.

**Nice-to-Have (preferred)**:

- Experience supporting founders or executives in early-stage startups.
- Exposure to CRM or financial administration tools.
- Familiarity with event coordination and vendor management.
- Experience handling executive communication and operational planning.

**Tools Proficiency**:
**Required**:

- Productivity: Google Suite (Docs, Sheets, Drive, Meet)
- Communication: Slack, Gmail, Zoom
- Project Management: Asana, Notion, ClickUp

**Preferred**:

- File Management: Dropbox, DocuSign, or similar platforms

**Benefits**:

- Competitive Salary: Based on experience and skills
- Remote Work: Fully remote—work from anywhere
- Growth Path: Opportunity to transition into a full