Executive Assistant to 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 — edu
365, Fleet
365, and Real Estate
365 — 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 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.

• 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

• 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, Whats App, and Linked In communications as directed
• Chase outstanding responses and keep communication threads moving

• 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

• 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

• 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

• 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

• 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, Power Point
• 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

• Experie…