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

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

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.

The ideal candidate is highly organized, resourceful, and thrives in startup environments where priorities shift quickly. You’ll manage core operations, streamline systems, and act as the founders’ trusted right hand across strategic and tactical initiatives.

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 and priorities.
Oversee calendars, meetings, and travel logistics for executives and key partners.
Maintain operational infrastructure including CRMs, shared drives, and productivity tools.
Serve as the main communication bridge between founders and teams or external stakeholders.

Recruiting & People Operations – 25%

Support hiring operations — posting jobs, screening candidates, and coordinating interviews.
Maintain candidate pipelines and assist in onboarding new hires.
Ensure documentation and HR processes are well-organized and easily accessible.

Project & Systems Management – 20%

Create and manage internal systems for task tracking, reporting, and documentation.
Streamline workflows to optimize founder and team productivity.
Handle ad-hoc strategic projects such as vendor coordination and event planning.

Communication & Coordination – 15%

Draft clear, professional correspondence and internal communications.
Anticipate founder and team needs; preempt blockers to maintain momentum.
Handle confidential information with discretion and professionalism.

Requirements

Must-Have (Required):

2–3+ years of experience as an Executive Assistant, 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:

CRM & Operations: HubSpot, Airtable, Monday.com
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-time Chief of Staff role
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
Top-grading Interview
Client Interview
Job Offer
Client Onboarding

Ready to Join Us?

If you’re a proactive operator who thrives in high-growth, founder-led environments and takes pride in creating order from chaos, we’d love to meet you. Apply now to become a trusted partner helping build and scale a fast-growing startup from the ground up.

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