Chief of Staff

We're looking for a **Chief of Staff** to act as the CEO's strategic right hand and force-multiplier across a growing group of companies spanning healthcare, media, and software. You will keep the CEO organised, informed, and focused; own the operating rhythm, priorities, and reporting; oversee day-to-day finance and operations; and take work off the CEO's plate across both business and personal life. This is not a traditional executive assistant role. You will own recruitment end to end, manage monthly financials, lead cross-functional projects, and represent the CEO with partners and suppliers as a trusted proxy. Full training on all company systems and processes will be provided — no prior healthcare experience is required. If you are highly organised, genuinely AI-native, proactive by default, and take pride in making a high-performing CEO more effective, this role is a strong fit. ### Why You'll Want to Join - You will be paid in **USD** (bi-monthly: every 15th and 30th) - **Paid Time Off** in accordance with company policy - Observance of **Holidays** per company guidelines - **100% remote setup** so you can work wherever you're most productive - This role requires availability during **UK business hours** - Act as a true strategic partner to a founder running multiple companies across healthcare, media, and software - High-ownership, high-trust role with direct impact on how the business operates day to day ### What You'll Work On **Executive Operations and Calendar Management** - Own the CEO's calendar end to end, protecting deep-work time, family commitments, and fixed priorities before adding anything new - Create clear, complete calendar invites with full context, colour-coded by type, and conflict-free at all times - Manage the CEO's inbox daily, surfacing only what requires his attention, drafting replies, and filing the rest - Prepare the CEO for every decision with options, context, and a clear recommendation - Run the operating rhythm including recurring team meetings, weekly reviews, and quarterly planning **Finance and Reporting** - Prepare the monthly profit and loss, run payroll, manage invoices, expenses, and budgets - Coordinate with the accountant on tax and ensure records are organised and current - Maintain simple dashboards and track key numbers across the group - Deliver board and leadership reports accurately and on time **Projects and Operations** - Lead cross-functional and special projects end to end with full ownership of timelines, quality, and delivery - Build, document, and continuously improve SOPs and systems across the business - Track KPIs, OKRs, and priorities across all companies and keep the team aligned and accountable - Manage vendor relationships, tool subscriptions, renewals, and negotiations - Coordinate contractors and external partners on active workstreams **Recruitment and People Operations** - Own recruitment end to end including writing job specs, sourcing and screening candidates, coordinating interviews, and managing offers - Build and maintain pipelines for both contractors and permanent hires - Run onboarding for new starters and maintain team records and light HR administration **Communications and Stakeholder Management** - Act as communication liaison for clients, partners, and suppliers - Manage follow-ups with leads and clients and support email campaigns - Represent the CEO as a trusted proxy with high-level partners and stakeholders - Prepare meeting agendas, notes, action lists, status reports, and slide decks **Personal and Family Support** - Manage the CEO's personal and family calendar including appointments, birthdays, and anniversaries - Plan family events, celebrations, travel, and holidays - Handle gifting, shopping, and personal admin including household management, bills, health appointments, and document renewals - Manage personal finances including budgeting, receipts, and liaison with personal advisers **AI-First Workflow** - Use AI tools daily inclu…