Chief of Staff (Executive Assistant)

Overseas; Gauteng; Remote; ZAR 1,997,000 - 2,995,000; Full time

Benefits offered by this job

Paid Time Off

100% remote setup

US business hours alignment

Job summary

Overseas is seeking a sharp, high-agency Chief of Staff (Executive Assistant) to own recruiting, offshore staff training, and operational support for a fast-growing AI healthcare startup. This generalist leadership role moves across functions, requires independence, and delivers outcomes without a predefined playbook.

If you are self-directed, highly organized, and comfortable with evolving scope, this role is a strong fit for you and your career growth.

Qualifications

• 8+ years in executive assistant, chief of staff, head of recruitment, or high-ownership generalist roles (hard requirement).
• Minimum of 2 years tenure at each employer; frequent changes may disqualify.
• Exceptional written and spoken English fluency for training and communication-heavy work.
• Ability to manage multiple complex workflows with minimal oversight.
• Comfort training and supporting team members at varying levels of experience.
• Strong organizational systems and consistent follow-through.

Responsibilities

• Recruiting and pipeline management across multiple boards with high volume.
• Offshore staff training and onboarding, developing materials and ensuring productivity from day one.
• Interview scheduling and coordination with calendar invites and lead times.
• Operations and navigation support, identifying gaps and proposing proactive solutions.

Skills

Executive support

Chief of Staff

Recruiting coordination

Training delivery

Operations coordination

English fluency

Independent work

Problem solving

Job description

We're looking for a sharp, high-agency Chief of Staff (Executive Assistant) to own recruiting, offshore staff training, and operational support for a fast-growing AI healthcare startup. This is a generalist leadership role built for someone who is genuinely all-around capable — someone who picks up new systems fast, runs independently, and delivers outcomes without needing a playbook handed to them.

You will spend a significant portion of your time recruiting and training offshore staff, but this role extends beyond that. You will also support navigation, operations, and other projects as they arise. What we are looking for is not a specialist — it is someone smart and versatile enough to move between functions without losing quality or momentum. If you are self-directed, highly organized, and thrive in an environment where your scope evolves alongside the business, this role is a strong fit.

Why You'll Want to Join

• You will be paid in USD (bi-monthly: every 15th and 30th)
• Paid Time Off in accordance with company policy
• Observance of Holidays per company guidelines
• 100% remote setup so you can work wherever you're most productive
• This role requires availability during US business hours
• Direct ownership over recruiting, offshore training, and operational support inside a growing healthtech startup
• High-agency, high-variety role with clear targets and the autonomy to hit them your way

What You'll Work On

Recruiting and Pipeline Management

• Source and move candidates through the funnel across multiple job boards with hundreds of applications weekly
• Review inbound applications same-day or next-day across all active platforms
• Screen candidates and move qualified applicants forward without waiting for direction
• Hit consistent hiring targets and keep the pipeline clean, current, and moving at all times
• Refine, publish, and iterate job descriptions based on performance data and team feedback

Offshore Staff Training and Onboarding

• Train newly hired offshore staff on tools, systems, workflows, and expectations
• Develop and improve training materials and onboarding documentation over time
• Ensure new hires are fully set up and productive before and from day one
• Flag setup gaps or blockers early so nothing falls through during onboarding
• Build and maintain a repeatable onboarding process that scales as the team grows

Interview Scheduling and Coordination

• Schedule all interview rounds with enough lead time to ensure a smooth candidate experience
• Send calendar invites at least 24 hours in advance across all interview stages
• Coordinate availability between candidates and interviewers without creating friction

Operations and Navigation Support

• Support operational projects and initiatives as assigned across the business
• Assist with navigation, process management, and internal coordination as needed
• Identify and flag operational gaps or inefficiencies and propose solutions proactivelyTake on ad hoc projects and new responsibilities as the business evolves

What You Bring

• 8 or more years of experience across executive assistant, chief of staff, head of recruitment, or high-ownership generalist roles — this is a hard requirement
• Demonstrated career stability with a minimum of 2 years tenure at each employer — candidates with frequent job changes of less than 2 years per role will not be considered
• Exceptional written and spoken English fluency at a professional or near-native level — this is required for a training and communication-heavy role
• Proven ability to manage multiple complex workflows simultaneously with minimal oversight
• Comfortable training and supporting team members at varying levels of experience and technical ability
• Strong organizational systems and a track record of following through without being reminded
• Ownership mindset — you surface problems with a proposed solution, not just a flag
• Genuinely versatile and adaptable with the ability to shift between recruiting, training, and operational work without losing quality

Nice to Have

• Prior exposure to recruiting, HR coordination, or candidate management
• Experience training or onboarding offshore or remote team members
• Experience in healthcare, healthtech, or a regulated industry
• Interest in or comfort with AI tools that could automate parts of the workflow
• Background in operations, project coordination, or chief of staff functions

Application Process Overview

Our comprehensive selection process ensures we find the right fit for both you and our clients:

1. Initial Application- Submit your application and complete our prequalifying questions
2. Video Introduction- Record an video introduction to showcase your communication skills and work experience
3. Role-Specific Assessment- Complete a homework assignment tailored to the position (if applicable)
4. Recruitment Interview- Initial screening with our talent team
5. Executive Interview- Meet with senior leadership to discuss role alignment
6. Client Interview- Final interview with the client team you'd be supporting
7. Background & Reference Check - Professional reference verification
8. Job Offer- Successful candidates receive a formal offer to join the team

Each stage is designed to evaluate your fit for the role while giving you insights into our company culture and expectations. We'll keep you informed throughout the process and provide feedback at each step.