Head Executive Assistant - REMOTE - AP000 at Pearl

Cape Town, Western Cape, South Africa -

Full Time

Start Date

Immediate

Expiry Date

27 May, 26

Salary

0.0

Posted On

26 Feb, 26

Experience

0 year(s) or above

Remote Job

Yes

Telecommute

Yes

Sponsor Visa

Skills

Executive Support, Calendar Management, Inbox Management, Communication, Organization, Time Management, Notion, Asana, SOP Creation, Process Improvement, Travel Coordination, Research, Problem-Solving, Confidentiality, Proactive Mindset, Follow-Through

Industry

Staffing and Recruiting

Description

Department: Admin and Executive Assistance Work Arrangement: Remote Job Type: Independent Contractor, Full Time Work Schedule: US Time Zone (candidate expected to be flexible with the client's preference) Locations: Philippines, LATAM, South Africa, Kenya, and other remote regions with excellent English communication skills About Pearl Talent Pearl works with the top 1% of candidates from around the world and connects them with the best startups in the US and EU. Our clients have raised over $5B in aggregate and are backed by companies like OpenAI, a16z, and Founders Fund. They're looking for the sharpest, hungriest candidates who they can consistently promote and work with over many years. Candidates we've hired have been flown out to the US and EU to work with their clients, and even promoted to roles that match folks onshore in the US. Hear why we exist, what we believe in, and who we're building for: WATCH HERE Why Work with Us? At Pearl, we're not just another recruiting firm—we connect you with exceptional opportunities to work alongside visionary US and EU founders. Our focus is on placing you in roles where you can grow, be challenged, and build long-term, meaningful careers. Role Overview The Executive Assistant serves as the operational backbone for founders, CEOs, and senior leadership teams in fast-paced startup environments. This role goes beyond traditional administrative work—you'll manage time, systems, and communication while anticipating needs before they arise, driving alignment across priorities, and enabling executives to focus on strategy, partnerships, and growth. This is a high-trust, high-autonomy position perfect for someone who thrives on solving operational challenges and is excited by the opportunity to scale into Chief-of-Staff–level responsibilities. Your Impact Your efforts will maximize executive leverage by managing time, tasks, and communication with precision. You'll build and maintain operational systems that enhance clarity and efficiency across the organization. Acting as a communication hub, you'll ensure updates, deliverables, and follow-ups never slip through the cracks. You'll drive accountability through structure, tools, and proactive problem-solving while continuously evolving operational workflows through automation and process improvement. Core Responsibilities Executive Support & Communication (35%) Manage executive calendars, inboxes, and priorities to ensure maximum productivity (aim for inbox zero) Draft, proof, and send professional internal and external communications on behalf of leadership Prepare meeting briefs, agendas, and follow-ups ensuring executives are always context-ready Coordinate meetings with internal and external stakeholders across multiple time zones Manage task lists and close 90%+ of delegated items within 48 hours Track deadlines, commitments, and action items to ensure timely execution Maintain proactive oversight of ongoing projects to ensure on-time delivery Operational Systems & Workflow Management (30%) Maintain dashboards and documentation in Notion, Asana, and other internal tools Create, update, and refine SOPs to improve consistency and operational efficiency Build structure around recurring workflows through automation and process mapping Monitor task completion and reduce recurring errors or missed deadlines Streamline recurring workflows and support cross-functional operational processes Facilitate team communication, shared workspaces, and progress tracking systems Support operations including vendor coordination and task management Calendar, Travel & Administrative Coordination (20%) Own complex calendar management including internal meetings, external calls, and priority-based scheduling Coordinate and book travel arrangements (flights, hotels, transportation) with detailed itineraries Handle inbox triage: flag urgent messages, draft replies, file emails, and ensure nothing slips through Support legal and administrative documentation (routing forms, signatures, deadline tracking) Coordinate personal appointments, reservations, and occasional household/vendor support as needed Protect executive time by managing schedule conflicts and ensuring adequate focus time Research, Documentation & Strategic Projects (15%) Conduct industry, competitor, and market research to support executive decision-making Compile concise briefs, summaries, and actionable insights from research Manage internal communications such as weekly team updates and stakeholder notes Research new tools and AI automations to improve operational speed and accuracy Support reporting on performance metrics, market trends, and strategic opportunities Identify potential issues early and propose proactive solutions Assist with special projects including light due diligence and business development initiatives Must-Haves (Required) Experience: 1-2+ years as an Executive Assistant, Admin Specialist, Operations Partner, or supporting C-level executives in fast-paced environments Executive Support: Proven ability to manage calendars, inboxes, and founder/CEO-level communication Communication: Excellent written and verbal English communication skills; clear, concise, and professional Organization: Exceptional attention to detail, organization, and time management capabilities Tech Proficiency: Comfortable with Google Workspace, Microsoft Office, and modern productivity tools Proactive Mindset: Strong ownership mentality with ability to anticipate needs and take initiative Discretion: High levels of confidentiality and professionalism when handling sensitive information Remote Experience: Demonstrated ability to work remotely with leaders across time zones Problem-Solving: Ability to think critically, manage competing priorities with urgency and precision Follow-Through: Demonstrated reliability in completing tasks and meeting deadlines consistently Nice-to-Haves (Preferred) Bachelor's degree preferred Background in healthcare, startups, AgTech, telecommunications, or project management Experience building SOPs, internal systems, or operational documentation Exposure to AI tools for automation and productivity enhancement Familiarity with analytics, reporting, or data-driven decision support Experience supporting M&A, investor relations, or due diligence processes Experience with CRM systems or project coordination tools Basic spreadsheet skills (sorting, filtering, formulas like SUM, IF, VLOOKUP) Prior startup or high-growth company experience Tools ProficiencyMust-Haves (Required) Email & Messaging: Gmail, Outlook, Slack, Microsoft Teams, WhatsApp Calendar & Scheduling Tools Google Workspace (Docs, Sheets, Drive, Calendar) Microsoft Office Suite (Word, Excel, PowerPoint) Zoom or equivalent video conferencing platforms AI Tools: ChatGPT, Claude, Perplexity, or similar AI assistants Nice-to-Haves (Preferred) Project Management: Notion, Asana, Trello, ClickUp, Airtable Automation: Zapier or similar workflow automation tools CRM Platforms: Pipedrive, HubSpot, Salesforce, ConnectWise Finance: QuickBooks or similar bookkeeping tools E-commerce: Amazon Seller Central, Shopify Communication: Loom for video messaging LinkedIn for professional networking and outreach Competitive Salary: Based on experience and skills Remote Work: Fully remote — work from anywhere Generous PTO: In accordance with company policy Direct Mentorship: Access to global industry leaders Learning & Development: Continuous growth resources Global Networking: Work with international teams Health Coverage (Philippines only): HMO after 3 months (full-time) Our Recruitment Process Application Skills Assessment Initial Screening Top-grading Interview Client Matching Job Offer Onboarding Ready to Join Pearl Talent? If you're a driven professional ready to work with exceptional founders building the next generation of world-class companies, we'd love to meet you. Apply now to unlock opportunities where your growth, impact, and success are our top priorities.

Responsibilities

The Executive Assistant will serve as the operational backbone for senior leadership by managing time, systems, and communication, ensuring executives can focus on strategy and growth. Core duties include executive support like calendar and inbox management, maintaining operational systems in tools like Notion and Asana, coordinating complex travel, and conducting research for strategic projects.