Executive Assistant / Chief of Staff (Job ID: HOLJAZ1EA)

Insideoutva; India; On-site; ZAR 630,000 - 720,000; Full time

Job summary

Insideoutva in South Africa seeks an Executive Assistant / Light Chief of Staff to manage executive calendars, prepare candidate materials, and support business development and events.

You will also handle personal administration across multiple properties, vendor management, and travel arrangements, ensuring timely, discreet, and high-quality support for the Managing Partner.

Qualifications

• Must be based in South Africa with alignment to working hours.
• Strong problem-solving, ownership, and independent work ethic.
• Fluent English with professional, PE/exec-level communication.

Responsibilities

• Coordinate complex multi-party interview logistics and scheduling.
• Build data-driven candidate presentations and dashboards.
• Manage personal and property administration, travel, and vendor relations.

Skills

Executive support

Scheduling

Data analysis

AI tools

Excel/Sheets

Vendor management

Tools

Claude AI

LinkedIn

Microsoft Office

Candidate testing portal

Job description

IMPORTANT - Watch this quick Loom video on how to get hired:

https://www.loom.com/share/345f776084e642ba99c24aabe40a67a0

C1 ENGLISH LEVEL IS REQUIRED, THE SELECTED CANDIDATE WILL BE SPEAKING STRICTLY IN ENGLISH DURING THEIR WHOLE SHIFT.

JOB TITLE: Executive Assistant / Chief of Staff

JOB ID: HOLJAZ1EA

INDUSTRY: Executive Search & Recruiting

LOCATION: South Africa

JOB STATUS: Full Time

WORK SCHEDULE: Monday to Friday, 8am to 5pm (Eastern Time)
with periodic flexibility required for evening or weekend candidate testing support and urgent priority updates.

SALARY: $3500 to 4000 Per Month

TARGET START DATE: ASAP

Role overview

About the client

The company is an executive search and recruiting firm with approximately two decades of experience serving high-level finance and private equity clients. Its work spans candidate sourcing, interview scheduling, and structured testing, supported by a proprietary candidate-testing portal developed and maintained by a dedicated South Africa-based technology division built during the past several years.

About the role

You will serve as a high-touch, dedicated Executive Assistant & Light Chief of Staff. On the business side, you will manage executive scheduling, build data-driven candidate presentations, assist with business development and event coordination, and provide live coverage for multi-hour candidate testing sessions.

On the personal side, you will act as a proactive operator across life and multi-property administration. You will manage vendor logistics, track recurring household maintenance, oversee personal accounts, and serve as an assertive right hand who keeps the Managing Partner organized, on time, and focused on strategic growth.

Key responsibilities

Recruitment Operations & Business Support (~40%)

• Executive & Candidate Scheduling: Coordinate complex multi-party interview logistics across private equity clients, candidates, and internal recruitment teams.


• Data Synthesis & Client Presentations: Build structured Excel/pivot tables and candidate slate summaries to present filterable data (e.g., GPA, university, technical background) for data-driven clients.


• AI & Workflow Automation: Utilize Claude and advanced AI tools to analyze candidate resumes, build dashboards, draft client collateral, and streamline operational SOPs.


• Testing Session Management: Serve as live proctor and tech-support standby during 3–4 hour candidate testing sessions (including early mornings or weekends), coordinating with candidates and technical proctoring teams.

Business Development & Marketing Logistics (~20%)

• Delegated Outreach: Execute targeted outreach campaigns directly through the Managing Partner’s LinkedIn account to prospective business development leads.


• Market Research: Conduct targeted research on prospective client firms, executive target lists, and geographic markets (e.g., San Francisco trip prep).


• Event Coordination: Manage logistics for client and marketing events, including tabulating RSVPs, catering arrangements, venue logistics, and post-event follow-up messages.

Personal & Multi-Property Administration (~40%)

• Preventive Property Tracking: Build and maintain an operational master calendar to track recurring service, inspections, and maintenance across multiple residential properties (e.g., HVAC servicing, specialized landscaping/arborist reviews, carpet cleaning).


• Vendor & Contractor Management: Research providers, gather multiple quotes, interface directly with contractors, and book property services.


• Financial & Life Oversight: Audit personal accounts, subscriptions, and vendor billing to flag duplicate charges or discrepancies; assist with document prep for tax filings.


• Travel & Personal Logistics: Handle personal calendars, family logistics, and detailed travel arrangements (flights, hotels, appointments).

Combined Qualifications & Core Competencies

Must-Haves & Non-Negotiables

• Location & Alignment: Must be based in South Africa to align seamlessly with the firm's existing technology team and working hours (including early morning or weekend testing support).


• Analytical & Proactive Oversight: Exceptional problem-solving skills and high ownership. Ability to work independently, analyze friction points, research complex topics/vendors, and deliver clear pros/cons recommendations rather than just executing basic tasks.


• Polished Communication: Flawless written and spoken English with a sophisticated, professional tone suitable for private equity executives, high-level clients, and candidates.


• Advanced AI Capability: High proficiency (or rapid adaptability) with AI tools—specifically Claude to automate research, analyze resumes, build dashboards, draft collateral, and streamline workflows.


• Data & Spreadsheet Mastery: Strong proficiency in Excel/Google Sheets, specifically building, formatting, and manipulating interactive pivot tables and structured candidate data sets.


• Communication & Time Management: High discretion, ruthless focus on driving tasks to completion, and comfort using modern communication channels (e.g., WhatsApp for quick updates and voice notes).


• Availability: Able to function as a dedicated near-full-time resource, dynamically balancing shifting priorities between business operations and personal administration.

Nice-to-Haves / Preferences

• Executive Search / Sourcing Background: Prior experience in recruitment operations, headhunting, or HR environments.


• Dual-Scope Experience: Proven track record supporting C-suite executives or high-net-worth individuals in a blended business and personal/household administration capacity.

Tech stack

• Claude (including Claude Cowork and Claude Design)


• LinkedIn


• Microsoft Suite (Excel pivot tables, Word, Outlook)


• Candidate testing portal


• Video conferencing tools


• WhatsApp