Executive Assistant to the CEO

About SIS Global

SIS Global is a Microsoft-platform digital transformation business operating across the USA, South Africa, the UK, and the Middle East. We deliver enterprise technology transformation through our vertical platforms — edu365, Fleet365, and RealEstate365 — built on Microsoft Dynamics 365, Azure, Power Platform, and Copilot. The CEO is based in Clearwater, Florida and operates globally across multiple time zones and business interests.

The Role

The CEO of SIS Global needs a sharp, reliable, and highly organized Executive Assistant based in Clearwater. This is a hybrid role — you work from home for most tasks but are available to come into the CEO's Clearwater office when needed for in-person meetings, document handling, and on-site support.

The CEO runs a globally distributed technology company, multiple corporate entities across five countries, and a charitable initiative building a school in South Africa. He is deeply hands-on across commercial, product, and strategic work. Your job is to protect his time, keep his world organized, and handle the personal and business coordination that currently lands on his desk.

A separate South Africa-based Executive Assistant handles the corporate secretarial, legal, and administrative workload. You focus on the CEO's personal and business coordination in the US.

What You Will Do

Calendar & Schedule Management

• Own the CEO's calendar across US, UK, South Africa, and Middle East time zones
• Schedule, confirm, and protect meetings — internal and external, virtual and in-person
• Resolve scheduling conflicts proactively and build in preparation and travel buffers
• Manage the CEO's day so he is always prepared and never double-booked

Communications

• Monitor and triage the CEO's email inbox — flag urgent items, draft responses, and clear noise
• Draft professional emails, follow-ups, and correspondence on behalf of the CEO
• Manage Teams, WhatsApp, and LinkedIn communications as directed
• Chase outstanding responses and keep communication threads moving

Travel & Logistics

• Research, book, and manage all domestic and international travel — flights, hotels, transfers, visas
• Build detailed itineraries with all confirmations, addresses, and contacts
• Anticipate disruptions and have contingencies ready before they're needed
• Manage expense receipts and submit reports on the CEO's behalf

In-Person Support — Clearwater

• Available to work from the CEO's Clearwater office when required — meetings, document handling, hosting visitors
• Manage the Clearwater office space — supplies, coordination, meeting setup
• Handle notarization, courier, and document delivery tasks locally
• Support in-person client and partner meetings as required

Meeting Preparation & Follow-Up

• Prepare briefing notes before every significant meeting — who, what, context, objectives
• Record and track action items from meetings
• Maintain a master action tracker and follow up with owners across time zones
• Coordinate with the SA-based Executive Assistant and SA-based Chief of Staff on joint tasks

Business & Personal Support

• Handle personal scheduling, appointments, errands, and ad hoc tasks as directed
• Research tasks — suppliers, venues, contacts, information — delivered quickly and accurately
• Support the CEO's involvement in the Imagine Charity where US coordination is needed
• Maintain full confidentiality across all business and personal matters at all times

What We Are Looking For

Required

• 3–6 years’ experience as an Executive Assistant or Personal Assistant supporting a C-suite executive
• Actively uses AI tools in your current work — Microsoft Copilot, ChatGPT, or equivalent — and can demonstrate this with real examples from the last 30 days
• Strong Microsoft 365 including Copilot — Outlook, Teams, Word, Excel, PowerPoint
• Based in or near Clearwater, Florida — you must be able to come into the office when needed
• Exceptional written and verbal English — professional, clear, and confident
• Proven calendar management across multiple time zones
• Absolute discretion and confidentiality — you will have access to sensitive business and personal information
• Proactive and self-managing — you anticipate what's needed without being asked

Advantageous

• Experience supporting a CEO or founder in a technology, professional services, or international business
• Familiarity with Microsoft Dynamics 365 or similar CRM tools
• Experience coordinating with teams across multiple countries and time zones
• Background working in a fast-moving, globally distributed organization

The Person We Are Looking For

You are calm, precise, and one step ahead. You manage a busy global CEO's day with confidence, and you take genuine pride in the fact that things run smoothly because of you. You are discreet with sensitive information, professional in every interaction, and completely reliable. You use AI tools naturally because they make you faster and better — not because someone told you to. You work well independently but you're also comfortable being physically present when the situation calls for it.

What SIS Global Offers

• A varied, high-trust role supporting a globally operating CEO
• Hybrid working — mostly remote with in-person presence in Clearwater when needed
• Exposure to international business across the USA, UK, South Africa, and Middle East
• Full Microsoft stack — Copilot, Teams, Dynamics 365, and the tools to do your job well
• Competitive salary: $45,000 – $65,000 per year based on experience
• A role that grows as the company grows

How to Apply

1.How do you currently use AI tools in your work? Give a specific example from the last 30 days.

2.Describe a time you managed a complex international travel itinerary under pressure.

***email_hidden*** · www.sisglobal.com