Executive Assistant / Admin Specialist (AI-Driven Ops Partner) - A148

Industry : AI / HealthTech / Operations

Work Arrangement : Fully Remote (US Time Zones)

Job Type : Independent Contractor, Full-time

Work Schedule : Flexible & asynchronous (40–48 hours per week; agility >

hours)

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.

Role Overview

We’re hiring an Executive Assistant / Admin Specialist (AI-Driven Operations Partner) to serve as the operational backbone for the founding team.

You’ll manage time, systems, and communication — anticipating needs before they arise, driving alignment across priorities, and enabling the founders to focus on strategy, partnerships, and growth.

This is a high-trust, high-autonomy role perfect for someone who thrives in startup environments, loves solving operational challenges, and is excited by the chance to scale with the company into a Chief-of-Staff–level position .

Your Impact

• Maximize founder leverage by managing time, tasks, and communication with precision.
• Build and maintain operational systems that enhance clarity and efficiency.
• Act as a communication hub — ensuring updates, deliverables, and follow-ups never slip.
• Drive accountability through structure, tools, and proactive problem-solving.
• Evolve operational workflows through automation and continuous improvement.

Core Responsibilities

Founder Support & Communication – 35%

• Maintain founder inboxes and calendars (aim for inbox zero).
• Draft, proof, and send professional internal / external communications.
• Prepare meeting briefs and follow-ups, ensuring founders are always context-ready.
• Manage task lists and close 90%+ of delegated items within 48 hours.

Operational Systems & Workflow Management – 30%

• Maintain dashboards and documentation in Asana , Notion , and internal tools.
• Create and update SOPs to improve consistency and efficiency.
• Build structure around recurring workflows through automation and process mapping.
• Monitor task completion, reducing recurring errors or missed deadlines.

Recruiting & Strategic Coordination – 20%

• Coordinate hiring pipelines and outreach for U.S.-based roles.
• Research, screen, and communicate with potential talent and vendors.
• Support partner development, scheduling, and coordination for business initiatives.

Documentation & Strategic Projects – 15%

• Manage internal communications such as weekly team updates and investor notes.
• Research new tools and AI automations to improve operational speed and accuracy.
• Identify potential issues early and propose proactive solutions.

Performance Expectations

• Inbox and calendar accuracy maintained at 100%.
• 90% of delegated tasks completed within 48 hours.
• Zero recurring workflow errors or missed deadlines.
• Two to three new SOPs created or improved each month.
• Meeting briefs always prepared ahead of key discussions.
• Anticipates 80% of potential issues before escalation.

Requirements

Must-Have (Required) :

• 3+ years of experience as an Executive Assistant, Admin Specialist, or Operations Partner .
• Strong written and verbal communication skills in English.
• Proven ability to manage calendars, inboxes, and founder-level communication.
• Tech-savvy and resourceful — skilled in Notion, Asana, Google Workspace, Slack , and automation tools ( Zapier , AI assistants).
• Exceptional attention to detail, organization, and time management.
• Proactive mindset with strong ownership and discretion in handling confidential information.
• Prior experience working directly with CEOs, founders, or startup leadership .
• Bachelor’s degree preferred.

Nice-to-Have (Preferred) :

• Background in healthcare, startups, or project management .
• Experience building SOPs or internal systems.
• Exposure to AI tools for automation and productivity.
• Familiarity with analytics, reporting, or data-driven decision support.

Tools Proficiency

Required :
• Notion
• Asana
• Google Workspace (Docs, Sheets, Drive, Calendar)
• Slack
• Zapier
Preferred :
• Airtable
• ChatGPT / AI Assistants
• LinkedIn / CRM systems
• Loom

Benefits

• Competitive Salary : Based on experience and skills
• Remote Work : Fully remote—work from anywhere
• Career Growth : Path to Chief-of-Staff within 2-3 years
• 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 proactive, hyper-organized, and passionate about helping founders operate at peak performance, we’d love to meet you. Apply now and help scale an AI-driven healthcare startup that’s reshaping patient advocacy.