Executive Assistant (Job ID: RICBEN1EA)

Insideoutva; South Africa; On-site; ZAR 365,000 - 456,000; Full time

Job summary

Insideoutva seeks an Executive Assistant/Chief of Staff to directly support the Co-CEOs and CFO. This high-touch, hybrid role blends strategic operational support with personal administration, balancing business and private workflows for top leadership.

The ideal candidate is proactive, tech-forward, and comfortable managing complex calendars, cross-functional coordination, and sensitive personal tasks with discretion.

Qualifications

• Exceptional verbal and written English communication skills.
• Spanish fluency is highly beneficial given the Texas location and customer base.
• Experience using AI as a daily productivity partner (Anthropic Claude, ChatGPT, Gemini, Google tools).
• Ability to work with high autonomy and strong judgment in strategic tasks.
• Adaptable and able to shift between strategic business tasks and personal admin.

Responsibilities

• Research and prepare high-level executive briefs, slide decks, and meeting materials ahead of key decisions.
• Pull data, manage reports, and maintain CRM records for leadership visibility.
• Create, refine, and document SOPs for recurring processes to build infrastructure.
• Manage complex executive calendars, filter priority communications, and protect focus time.
• Coordinate between co-CEOs to ensure delegation boundaries and alignment across remote teams.
• Handle high-level personal tasks including travel, insurance calls, dining reservations, and vendor management.

Skills

Executive communication

Spanish bilingual

Claude AI

ChatGPT

Gemini

Google Tools

Autonomy

Cultural fit

Tools

Anthropic Claude

ChatGPT

Gemini

Google Workspace

RingCentral

Custom internal CRM

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.