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 including Claude and ChatGPT as a core part of how you work, not as an afterthought

Use AI to research, draft, summarise, and produce fast, high-quality first versions of documents, emails, and reports

Continuously identify opportunities to automate and optimise processes using AI

Build and maintain AI-assisted workflows and documents across the business

What You Bring

Proven experience as a Chief of Staff, Executive Assistant, or Operations Lead supporting a founder or CEO, remote experience welcome

Strong organisational and project management skills with the ability to manage multiple priorities across parallel workstreams simultaneously

Solid finance and bookkeeping competency including profit and loss preparation, payroll, expense tracking, and budget management

Genuinely AI-native with confidence using Claude, ChatGPT, and similar tools daily for research, drafting, and workflow optimisation

Excellent written English with a clear, professional, and warm communication style

Highly proactive, reliable, and discreet with the ability to handle sensitive business and personal information with full confiden…