Personal assistant to CEO

Executive & Lifestyle Manager to the CEO SESSA Design & Sourcing | RJ's Hospitality Services | CEO Personal Affairs Position Overview SESSA Design & Sourcing and RJ's Hospitality Services are seeking an exceptional Executive & Lifestyle Manager to become the right hand to the CEO. This is not a traditional Executive Assistant role. The successful candidate will serve as the central coordinator for the CEO's business activities, personal affairs, international travel, scheduling, relationships, and lifestyle management. The ideal candidate is highly organized, proactive, resourceful, discreet, and capable of anticipating needs before they arise. They must be comfortable managing multiple priorities across different countries, time zones, and business entities while maintaining complete confidentiality. The objective of this role is simple: Create more time, less stress, and a smoother life for the CEO. About the CEO The CEO operates multiple businesses throughout the Caribbean, United States, and China, including: SESSA Design & Sourcing RJ's Hospitality Services Luxury hospitality development projects International sourcing and manufacturing operations Real estate and resort development projects The CEO travels extensively throughout: Saint Lucia Grenada Barbados Antigua Turks & Caicos United States China Europe The Executive & Lifestyle Manager will become the primary coordinator ensuring both business and personal affairs run seamlessly. Core Responsibilities Executive Support Calendar Management Manage CEO's personal and professional calendar Coordinate meetings across multiple time zones Resolve scheduling conflicts proactively Schedule recurring meetings Ensure adequate travel and preparation time between appointments Maintain daily, weekly, and monthly planning calendars Daily Briefings Prepare a Daily CEO Briefing each morning including: Calendar appointments Travel schedule Follow-up items Outstanding approvals Upcoming birthdays and events Personal reminders Business priorities Pending decisions Communication Management Draft emails and correspondence Follow up on outstanding requests Coordinate communication with team members Track commitments made by CEO Ensure deadlines are not missed Assist with presentation preparation Travel Management Complete Travel Planning Responsible for all aspects of travel including: Flights Research optimal flight routes Identify best pricing opportunities Utilize travel hacks and loyalty programs Track fare changes Manage upgrades when possible Coordinate changes and cancellations Accommodations Source best hotel options Negotiate rates when possible Utilize loyalty memberships Arrange upgrades and VIP requests Coordinate early check-in and late check-out Ground Transportation Airport transfers Rental cars Private drivers Ferry and boat transportation Yacht charters when required Travel Documentation Passport tracking Visa requirements Travel insurance Entry requirements Immigration forms Travel Itineraries Create professional travel packets including: Flight details Hotel confirmations Driver information Restaurant reservations Meeting schedules Emergency contacts Personal Lifestyle Management Personal Administration Manage all personal logistics including: Relationship Management Birthday tracking Anniversary tracking Gift planning Flower orders Holiday gifts Thank-you gifts Personal correspondence Social Coordination Dinner reservations Event bookings Entertainment planning Special occasions Family events Friend gatherings Personal Appointments Medical appointments Wellness appointments Fitness scheduling Grooming appointments Personal errands Personal Projects Coordinate special projects Research purchases Home-related management Vendor coordination Business Coordination Cross-Department Coordination Work closely with: CEO Finance Department Accounting Team Operations Team China Office Sourcing Team Project Managers Responsibilities include: Tracking action items Following up on deliverables Monitoring deadlines Coordinating communication Organizing project updates Event & Hospitality Coordination Manage: Client dinners Networking events Investor meetings Hotel site visits Corporate events Special celebrations Responsibilities include: Venue selection Reservation management Guest coordination Transportation logistics Event follow-up Technology & Systems Maintain proficiency in: Required Google Workspace Gmail Google Calendar Google Drive Google Docs Google Sheets Microsoft Office Zoom Asana Preferred QuickBooks Canva Notion Slack AI tools (ChatGPT, Gemini, etc.) CRM systems Key Performance Indicators (KPIs) Success in this role will be measured by: Organization Calendar accuracy Missed appointment prevention Travel readiness Responsiveness Timely follow-up completion Response time to requests Deadline management Proactivity Anticipation of needs Identification of potential issues Problem-solving ability Travel Excellence Cost savings achieved Upgrade opportunities secured Travel disruptions minimized Personal Support Birthday and gift management accuracy Personal event coordination Relationship management support Ideal Candidate Profile Required Qualities Highly organized Exceptional attention to detail Strong written and verbal English Professional demeanor Resourceful and proactive Strong problem-solving abilities Able to maintain confidentiality Calm under pressure Excellent judgment Preferred Experience Executive Assistant experience Lifestyle Manager experience Chief of Staff support experience Luxury hospitality experience Travel concierge experience International business support Work Schedule This role requires flexibility. The CEO operates internationally and frequently travels across multiple time zones. The candidate must be comfortable responding to urgent matters outside traditional business hours when necessary. Compensation Competitive compensation based on experience. Performance bonuses available based on: Efficiency improvements Travel savings KPI achievement Overall performance The Ideal Outcome The successful candidate becomes the CEO's trusted operational partner. Their job is to ensure that: Every trip is organized. Every meeting is prepared. Every birthday is remembered. Every gift is sent. Every reservation is booked. Every deadline is tracked. Every detail is handled. The Executive & Lifestyle Manager should be able to anticipate needs before they are requested and create a world where the CEO can focus on growth, relationships, strategy, and living life rather than managing logistics.