Executive Assistant (Job ID: OSBSAM1EA)

Insideoutva; South Africa; On-site; ZAR 449,000 - 539,000; Full time

Job summary

Insideoutva in South Africa is seeking an experienced Executive Assistant to act as the Founder’s right-hand, taking administrative and team-management duties off the plate. You will track team deliverables, establish cadence, and leverage Claude to audit internal processes, write SOPs, build dashboards, and streamline daily operations.

You will coordinate travel, manage schedules, and provide clear reporting on risks, timelines, and progress.

Qualifications

• 3+ years supporting Founders, CEOs, or Agency Owners directly in an EA or Operations role.

Responsibilities

• Executive Support & Administrative Operations: Manage calendar scheduling, inbox prioritization, and high-level secretarial tasks to free up the Founder’s time for growth initiatives.
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Skills

Executive support

Process & SOP creation

Team cadence & accountability

Clear reporting

Google Workspace proficiency

ClickUp proficiency

Slack proficiency

AI literacy (Claude)

Tools

Google Workspace

ClickUp

Slack

Job description

Job Title: Executive Assistant

Job ID: OSBSAM1EA

Industry: Digital Media

Location: South Africa / LATAM

Job Status: Full Time

Work Schedule: Monday to Friday, 9:00am to 5:00pm (EST)

Salary: $2500 to $3000 per month

Target Start Date: ASAP

About the Client:

Our client operates a boutique digital media, narrative strategy, and growth marketing studio that functions as part of a broader technology and media ecosystem. Rooted in research-driven strategies, media buying, performance marketing, and high-standard visual storytelling, the firm helps select brands, founders, and partners build long-term market mindshare. The company operates lean and intentionally—combining high-level strategic craft with internal AI technologies and operational automation.

About the Role:

This is a high-leverage position acting as the operational right-hand to the Founder. You will be stepping in to take administrative and team management responsibilities entirely off the Founder’s plate, allowing leadership to focus on high-revenue strategic work.

Rather than a traditional administrative role, you will be heavily involved in tracking team deliverables, establishing cadence, and utilizing advanced AI tools (specifically Claude) to audit technical processes, write SOPs, build dashboards, and streamline daily operations.

Key Responsibilities

• Executive Support & Administrative Operations: Manage calendar scheduling, inbox prioritization, and high-level secretarial tasks to free up the Founder's time for growth initiatives.


• Team Accountability & Progress Tracking: Oversee day-to-day team execution, establish operational cadences, track task completion, and proactively clear roadblocks so the Founder doesn't have to chase updates.


• AI-Driven Operations & SOP Building: Leverage Claude to document internal systems, generate operational SOPs, build reporting dashboards, and convert manual workflows into automated processes.


• Technical Audits & Process Documentation: Use AI tools alongside the Founder to audit basic code repositories, review technical documentation, and eliminate key-person operational risks.


• Transparent Communication & Reporting: Provide real-time, accurate reporting on team progress, operational risks, and project timelines.


• Travel & Personal Admin (Life Admin): Manage end-to-end business travel logistics (booking flights/hotels, negotiating room upgrades), handle mail forwarding setups, manage password security/access, handle personal reservations, orders, and routine personal logistics.


• External Process & Operational Research: Review external documentation, vendor requirements, and setup processes (e.g., setting up direct mail campaigns, permits, mailboxes) and translate complex requirements into actionable internal SOPs.

Required Skills & Qualifications

• Executive Support Background: 3+ years supporting Founders, CEOs, or Agency Owners directly in an EA or Operations role.


• Process & SOP Creation: Proven ability to document, organize, and maintain detailed Standard Operating Procedures (SOPs) across various agency functions.


• Team Accountability & Cadence: Strong delegation tracking skills—monitoring deliverable timelines for team members (media buyers, admins, developers) without needing micro-management.


• Clear Communication & Reporting: Ability to provide concise daily/weekly summaries highlighting task status, light workloads, blockers, and items needing direct Founder sign-off.


• Tool Proficiency: Strong proficiency in Google Workspace, ClickUp, Slack, task boards, and standard cloud-based operational tools.


• High Technical Comprehension & Fast Research: Ability to digest detailed external guides, technical documentation, or service setup requirements quickly and execute them correctly.

Non-Negotiables

• Radical Candor & Extreme Ownership: Absolute operational transparency. You flag delays, broken processes, and bottlenecks immediately rather than hiding behind passive reassurances or telling leadership what they want to hear.


• Advanced AI Technical Literacy: Daily experience using Claude (or similar LLMs) as a thinking partner to analyze data, resolve operational issues, write documentation, and perform basic technical/repository status audits.


• Proactive Self-Reliance & Critical Thinking: A default setting of independent problem-solving—you exhaust AI, help desks, and online documentation before escalating questions to the Founder. You act as a gatekeeper and solution-provider (e.g., adjusting schedules around open calendar blocks independently rather than asking for instructions).


• Fluent Professional English: Native or flawless spoken and written English with zero communication friction.

Technical & AI Tool Stack

• Core Workspace: Google Suite (Docs, Sheets, Gmail, Calendar), ClickUp.


• AI & Automation Tools: Advanced daily usage of AI Tools (Claude, ChatGPT, Cursor, AWS, Coolify, and willingness/ability to leverage open-source/automated framework tracking tools e.g., OpenClaw, MixClaw).

Nice-to-Haves

• Digital Agency Experience: Prior exposure to programmatic advertising, digital media buying, or performance marketing environments.


• Basic GitHub/Technical Familiarity: Conceptual understanding of code repositories, GitHub workflows, or software development lifecycles (ability to direct Claude to audit repo progress).


• Asset & Deck Creation: Experience using AI design or document-building features (e.g., Claude Artifacts, Canva) to create clean pitch decks or client-facing slide decks.


• Bilingual Capability: Conversational or professional Spanish (if interacting with Latin American team members or partners).