Executive Assistant

Executive Assistant To Founders

Location: Remote (Latin America preferred; U.S. Eastern Time overlap required)

Employment Type: Full-Time (40 hours/week, Monday–Friday + occasional flexibility)

Time Zone Alignment: Full-time availability during U.S. Eastern Time (ET) business hours (9:00 AM – 5:00 PM ET base, with flexibility as business needs dictate).

Salary: Dependant on location and experience

• Philippines: $1400 - $1800
• South Africa: $1700 - $2200
• LATAM: $2000 - $2400
• Canada: TBD

Experience Level: 3–5+ years supporting executives/founders (Startup experience highly valued)

Industry: Healthcare Technology / Medicare & Medicaid Access

About The Company

Our client is a fast-growing healthcare technology company on a mission to simplify access to essential healthcare benefits. Our free platform helps individuals discover, understand, and enroll in Medicaid and Medicare benefits tailored to their unique needs.

As our team and operations rapidly expand, our founders need a high-caliber administrative partner to take ownership of operational, administrative, and personal workflows so leadership can stay focused on strategic growth and company building.

Role Overview

We are seeking a highly proactive, tech-savvy, and resourceful Executive Assistant (EA) to provide direct administrative support to two company founders (with primary support focused on the Chief Executive).

This is not a basic administrative support position. We are looking for an exceptional individual who operates like a Chief of Staff in the making —someone who thrives in a fast-paced, dynamic startup environment, handles both business and personal administrative tasks with total discretion, and proactively builds systems to streamline executive workflows.

The ideal candidate brings strong independent judgment, advanced proficiency with modern AI tools, native-level or fluent English (bilingual in Spanish is a strong plus), and a valid passport for travel to annual company-wide offsites.

Key Responsibilities

Executive & Founder Support

• Proactive Gatekeeping & Workflow Management: Protect founders' focus time, track outstanding commitments, manage action items, and ensure critical tasks are completed without requiring repeated follow-up.
• Meeting Preparation & Context Briefing: Prepare agendas, gather documentation, research background details, and brief executives prior to internal and external commitments.
• Administrative Ownership: Handle complex paperwork, documentation, forms, and time-consuming administrative tasks on behalf of leadership.
• Discretion & Trust: Manage highly sensitive business, financial, and personal information with absolute confidentiality and integrity.

Inbox & Communication Triage

• High-Volume Email Management: Monitor, organize, and triage high-volume founder inboxes.
• Independent Execution: Determine which emails require direct executive attention versus those that can be drafted, answered, or delegated independently.
• Follow-Up & Tracking: Draft professional responses, follow up on pending items, and ensure zero critical messages fall through the cracks.

Calendar & Schedule Optimization

• Strategic Calendar Management: Coordinate complex internal and external meetings across multiple time zones while safeguarding deep-work blocks for founders.
• Conflict Resolution: Proactively identify and resolve scheduling overlaps or logistics issues before they impact executive availability.

Personal & Logistics Support

• Business & Personal Integration: Seamlessly transition between company operational tasks and personal administrative requests (e.g., personal travel arrangements, reservations, scheduling, family coordination).
• Travel & Event Logistics: Coordinate travel itineraries, accommodation, and logistics for executive travel and company-wide offsites. Note: You will be invited to attend and help facilitate select company offsites in person.

AI, Automation & Process Efficiency

• AI-Powered Workflows: Actively leverage AI tools (e.g., ChatGPT, Claude, Gemini) to summarize information, draft communications, conduct research, and automate repetitive administrative tasks.
• Systems Architecture: Identify operational bottlenecks and implement improved digital filing, tracking, and communication systems rather than simply maintaining existing ones.

Research & Special Projects

• Independent Research: Conduct fast, thorough web research on diverse topics and present clear, synthesized summaries to leadership.
• Data & Presentation Support: Build spreadsheets, execution trackers, slide decks, and supporting materials for business initiatives.

Required Qualifications

• Experience: 3–5+ years of experience as an Executive Assistant, Virtual Assistant, or Operations Assistant directly supporting C-level executives or startup founders.
• Language Skills: Exceptional written and spoken English proficiency (C1/C2 level).
• Travel Readiness: Valid passport and willingness/ability to travel internationally to attend annual in-person company offsites (all expenses paid by company).
• Technical Mastery: Advanced proficiency with Google Workspace (Gmail, Calendar, Docs, Sheets, Drive) and modern productivity tools.
• AI Tool Fluency: Practical experience integrating generative AI tools into daily workflows to increase speed and execution quality.
• Security & Trust: Highest level of personal integrity, suitable for handling sensitive accounts, booking tools, and confidential company information (background and reference checks required).

Preferred Qualifications

• Startup/High-Growth Background: Prior experience navigating the ambiguity, speed, and shifting priorities of an early-stage or scaling technology startup.
• Bilingual Capability: Fluency in Spanish (spoken and written).
• Location: Based in Latin America (for optimal time zone alignment and travel logistics).
• Growth Mindset: Ambition to take on expanding responsibilities and grow into an operational leadership or Chief of Staff role over time.

Technical & Security Environment

Candidates should be proficient in or adaptable to working within the following setup:

• Core Stack: Google Workspace, AI platforms (ChatGPT/Claude/Gemini), Slack, web conference platforms.
• Security & Compliance: Compliance with company security standards, including working within enterprise-managed secure browsers (e.g., Island Browser) and password management tools.

What We Offer

• Founder-Level Exposure: Direct daily interaction with decision-makers, offering deep insight into startup operations and executive leadership.
• Career Growth: Clear opportunity to scale your scope of work as the company grows.
• Modern Tooling Environment: Freedom and encouragement to introduce AI and automation tools to optimize your workflow.
• In-Person Connection: Fully company-funded travel to attend team offsites and gatherings.