Executive Assistant (Job ID: RICBEN1EA)

Inside Out Hiring; United States; Hybrid; USD 22,000 - 28,000; Full time

Job summary

Inside Out Hiring in the United States is seeking a high-capability Executive Assistant / Chief of Staff to act as a direct proxy to our executive team. This is a hybrid, high-trust role balancing strategic business operations with personal administrative flows.

Key responsibilities include strategic CRM management, calendar ownership, and discreet handling of life-admin tasks. English fluency is essential; Spanish is a strong plus, and comfort with AI tools is expected.

Qualifications

• Executive Communication: Exceptional verbal and written English communication skills.
• Bilingual Spanish: Strongly preferred given Texas location and client base.
• AI Tool Integration: Experience using AI daily (Claude, ChatGPT, Gemini, Google tools).
• High Autonomy & Judgment: Resourceful problem-solver who works independently.
• Adaptability & Cultural Fit: Reliable and able to shift between strategic tasks and life admin.

Responsibilities

• Strategic Business Support & CRM: conduct high-level research and prepare briefs, decks, and materials.
• Executive Admin & Calendar: manage complex calendars and protect leadership focus time.
• Life Admin: handle personal tasks for senior leaders with discretion and reliability.

Skills

Executive Communication

Spanish bilingual

AI Tool Integration

Autonomy & Judgment

Adaptability & Culture Fit

Tools

Google Workspace

RingCentral

CRM System

Anthropic Claude AI

Job description

• Job Title: EXECUTIVE ASSISTANT


• Job ID: RICBEN1EA


• Industry: Healthcare


• Location: LATAM / South Africa


• Contract Type: Full Time


• Work Schedule: Monday to Friday, 8:00am to 5:00pm flexible (CST)


• Salary: $2000 to $2500 per month


• Target Start Date: ASAP

About the Client:

Our client operates a virtual clinical network managing a nationwide association of healthcare providers and physicians within the U.S. personal injury healthcare space. Headquartered in Texas, they bridge clinical networks with contingency-based care models, financial services, and AI-driven care coordination platforms.

The company maintains a lean, highly effective management team overseeing an expansive clinical association. Their work culture is family-oriented, flexible, and built on mutual respect and partnership—operating with low friction, high trust, and zero micromanagement.

About the Role

We are looking for a high-capability Executive Assistant / Chief of Staff to act as a direct proxy and operational partner to our executive team (Co-CEOs / CFO). This is not an ordinary task-driven Virtual Assistant role. It is a high-touch hybrid position—part strategic operational bridge, part high-trust private EA—designed to provide structure, streamline leadership focus, and handle both business and personal administrative flows.

Both executives are self-sufficient but ready to delegate control to the right person. If you are proactive, tech-forward, and comfortable seamlessly balancing executive business operations with personal "life admin", you will thrive here.

Key Responsibilities

1. Strategic Business Support & CRM Management

• Research & Preparation: Conduct high-level business research and prepare comprehensive executive briefs, slide decks, and meeting materials ahead of key decision-making sessions.


• CRM & Data Reporting: Pull data, manage reports, and maintain accurate records within the business CRM to ensure leadership has clear visibility into core metrics.


• SOP & Process Documentation: Create, refine, and document standardized operating procedures (SOPs) for recurring processes to build lasting business infrastructure.

2. Executive Administration & Calendar Ownership

• Calendar & Communication: Proactively manage complex executive calendars, filter priority communications, and protect leadership’s focus time.


• Cross-Executive Alignment: Coordinate seamlessly between co-CEOs, establishing clear delegation boundaries and operational syncs to build trust and alignment across remote structures.

3. Executive Personal Administration ("Life Admin")

• Handle high-level personal tasks for senior leadership, including complex travel arrangements, personal insurance calls, dining/venue reservations, and vendor management.


• Manage sensitive personal projects with total discretion, reliability, and precision.

Qualifications & Attributes

• Executive Communication: Exceptional verbal and written English communication skills.


• Bilingual Capability (Spanish): Strongly Preferred / Highly Beneficial given our Texas location and customer base (Spanish fluency is a major asset).


• AI Tool Integration: Active experience using AI as a daily productivity partner. Familiarity with Anthropic Claude (our core internal platform) alongside ChatGPT, Gemini, or Google native tools is a strong plus.


• High Autonomy & Judgment: Resourceful problem-solver with strong common sense. You don't need step-step instructions—you spot friction and address it independently.


• Adaptability & Cultural Fit: Grounded, reliable, and comfortable shifting effortlessly from strategic business tasks to everyday personal admin.

Tech Stack: Google Workspace native, RingCentral, custom internal CRM, Anthropic Claude AI platform.